5388-42-1 | - Indole Building Blocks

Prey, V. et al. published their research in Monatshefte fuer Chemie in 1958 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Electric Literature of C14H11NO

1-Thiophthalide was written by Prey, V.;Kondler, P.. And the article was included in Monatshefte fuer Chemie in 1958.Electric Literature of C14H11NO This article mentions the following:

Treatment of 1-thiophthalide (I) with PhNH₂ at 190鎺?in a bomb tube resulted in a rearrangement to 2-thiophthalide (II). The mechanism of the rearrangement is discussed. Phthalide (6.7 g.) and 11.1 g. P₂S₅ in xylene refluxed 1 hr., the mixture filtered hot, the filtrate steam distilled, the residue cooled, the oily product filtered off, pressed, and recrystallized twice from absolute EtOH gave 4.5 g. I, m. 108-9鎺? mol. weight 148.6. Proof of structure was supported by hydrolysis of I to phthalide, m. 73鎺? detection of the CS group by treatment of I with 0.5N alc. KOH and several drops of 30% H₂O₂, warming, cooling, acidifying, and adding BaCl₂ to obtain BaSO₄, and detection of the CS group by Grote’s test (C.A. 25, 5876). I treated with HgCl₂ 1 in Et₂O 15 parts gave I-Hg Cl₂ adduct (III), decompose 185鎺? III treated with saturated aqueous KI decomposed with the formation of HgS. I (2.0 g.) and 5.0 g. freshly distilled PhNH₂ refluxed 5 hrs. at 185鎺? cooled, the precipitate filtered off, and washed with dilute HCl and dried gave 1.02 g. N-phenylphthalimidine (IV), m. 165鎺? from the filtrate was obtained 0.7 g. addnl. IV. I (2.0 g.) and 5.0 g. PhNH₂ heated 3 hrs. at 190鎺?in a bomb tube, the mixture treated with dilute HCl, the oily precipitate dried in vacuo, taken up in EtOH, filtered, EtOH removed from the filtrate, and the product recrystallized from tetrahydrofuran with C and then from H₂O gave 1.65 g. II, white needles, m. 57-8鎺? I and PhNH₂ heated 3 hrs. at 240鎺?in a bomb tube gave 94% IV, m. 164鎺? II (2.0 g.) and 5.0 g. PhNH₂ refluxed 12 hrs. at 185鎺? cooled, the mixture treated with 50 cc. 20% HCl, and the resulting precipitate crystallized from EtOH gave 1.8 g. unchanged II, m. 57-8鎺? II (2 g.) and 5.0 g. PhNH₂ heated 3 hrs. at 190鎺?gave 95% unchanged II, but this mixture heated 3 hrs. at 240鎺?gave 2.45 g. IV, m. 164-5鎺? IV (2.0 g.) and 5.0 g. PhNH₂ contained in a bomb tube treated with dry H₂S with cooling at -78鎺? the tube sealed, and heated 3 hrs. at 190鎺?gave only unchanged IV. A similar result was obtained by heating at 240鎺? I (2.0 g.) and 5.8 g. PhNHMe refluxed 4.5 hrs. gave only 1.8 g. unchanged I. A similar result was obtained by heating 3 hrs. at 190鎺? Similar unsuccessful results were obtained using I and PhNMe, I being recovered. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Electric Literature of C14H11NO).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from鑱紹acillus thuringiensis鑱絘nd鑱紹acillus velezensis鑱絘nd their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Parham, William E. et al. published their research in Journal of Organic Chemistry in 1976 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Reference of 5388-42-1

Selective halogen-lithium exchange in bromophenylalkyl halides was written by Parham, William E.;Jones, Lawrence D.;Sayed, Yousry A.. And the article was included in Journal of Organic Chemistry in 1976.Reference of 5388-42-1 This article mentions the following:

Exchange of the aryl halide atom in o-BrC6H4CH2Cl, o-BrC6H4(CH2)2Br, and o-BrC6H4(CH2)3Cl for Li was carried out with BuLi in THF-hexane at -100掳. The stable lithio derivatives reacted with a variety of electrophiles; e.g., o-LiC6H4CH2Cl (I) with H2O, cyclohexanone, or PhNCO at low temperature gave, resp., PhCH2Cl, II, and III. I with H2O at room temperature gave 9,10-dihydroanthracene (not benzocyclopropene). Benzocyclobutene was formed from o-LiC6H4(CH2)2Br under similar conditions. O-halobenzyl bromides were lithiated at the benzyl bromine atom and underwent subsequent coupling to bibenzyl. O-BrC6H4(CH2)3Br with BuLi underwent intramol. coupling to indan. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lai, Huifang et al. published their research in Organic Chemistry Frontiers in 2022 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole could be stereoselectively alkylated with chiral cyclopentyl sulfone reagent. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Application In Synthesis of 2-Phenylisoindolin-1-one

Chemo-selective control of Ritter-type reaction by coordinatively unsaturated inorganic salt hydrates was written by Lai, Huifang;Xu, Jiexin;Lin, Jin;Su, Biling;Zha, Daijun. And the article was included in Organic Chemistry Frontiers in 2022.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

The Ritter-type reaction, without relying on a pre-installed functional group, is a highly efficient tool for the construction of amides. However, the intrinsic chemo-selectivity that determines the generation of amides or byproducts limits the efficiency and yield of the reaction. From 68 different types of hydrates studied, a coordinatively unsaturated inorganic salt hydrate, MgSO₄路2H₂O, controlled chemo-selectivity and eliminated the shortcomings of other synthesis approaches. To rationalize the differences in selectivity of inorganic salt hydrates, their corresponding water content, alkalinity, anions and cations were analyzed. MgSO₄路2H₂O was used with diverse scaffolds and C-H oxygenations, which demonstrated its generality in synthetic utility. Because it is readily available and it significantly improves yield, MgSO₄路2H₂O will have broad application for Ritter-type reactions. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

Lewis, Frederick D. et al. published their research in Journal of Physical Chemistry A in 2002 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Moreover, it is known that it controls biofilm formation. However, the role of indole in the cell has not been fully elucidated.Reference of 5388-42-1

Temperature- and Conformation-Dependent Luminescence of Benzanilides was written by Lewis, Frederick D.;Liu, Weizhong. And the article was included in Journal of Physical Chemistry A in 2002.Reference of 5388-42-1 This article mentions the following:

The luminescence of benzanilide, N-methylbenzanilide, and two cyclic analogs has been investigated as a function of temperature both in microcrystals and in the glass-forming solvent methyltetrahydrofuran. Potential energy surfaces for small-amplitude geometric relaxation of the excited states and large amplitude twisting about the amide bond in the ground and excited states have been explored using AM1 and RCIS calculations, resp. ZINDO calculations have been used to probe the electronic configuration of the planar and twisted singlet and triplet states. Correlation of the spectroscopic and computational results indicates that at 77 K benzanilide phosphorescence occurs from a planar 蟺,蟺* triplet state whereas fluorescence occurs from a singlet state with partially relaxed geometry. At higher temperatures, large-amplitude geometric relaxation results in the formation of an intramol. charge-transfer (TICT) state that is twisted about the amide C-N bond. This TICT state is responsible for the weak Stokes-shifted fluorescence observed from benzanilide and N-methylbenzanilide in fluid solution Inhibition of amide twisting in cyclic derivatives precludes observation of TICT fluorescence. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

Papa, Veronica et al. published their research in Catalysis Science & Technology in 2020 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Related Products of 5388-42-1

Homogeneous cobalt-catalyzed deoxygenative hydrogenation of amides to amines was written by Papa, Veronica;Cabrero-Antonino, Jose R.;Spannenberg, Anke;Junge, Kathrin;Beller, Matthias. And the article was included in Catalysis Science & Technology in 2020.Related Products of 5388-42-1 This article mentions the following:

The first general and efficient cobalt-catalyzed deoxygenative hydrogenation of amides, e.g., I to amines, e.g., II is presented. The optimal catalytic system based on a combination of [Co(NTf₂)₂] and (p-anisyl)triphos in the presence of [Me, ₃SiOTf] as acidic co-catalyst facilitates the direct hydrogenation of a broad range of amides, e.g., I to the corresponding amines e.g., II under mild conditions. A set of control experiments indicate that, after the initial reduction of the amide carboxylic group to the well-known hemiaminal intermediate, the reaction mainly proceeds through C-O bond cleavage though other pathways might be also involved to a minor extent. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Related Products of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. The indole subunit is an almost ubiquitous component of biologically active natural products, and its study has been the focus of research for decades. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Related Products of 5388-42-1

O’Connell, E. J. Jr. et al. published their research in Photochemistry and Photobiology in 1971 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Application In Synthesis of 2-Phenylisoindolin-1-one

Absorption and emission studies of electronic states of N-arylbenzamides was written by O’Connell, E. J. Jr.;Delmauro, M.;Irwin, J.. And the article was included in Photochemistry and Photobiology in 1971.Application In Synthesis of 2-Phenylisoindolin-1-one This article mentions the following:

Absorption and emission spectra of benzanilide, 1-naphthamide, N-phenylphthalimidine, naphthalene, BzNMePh and AcNHPh were obtained in solvents such as EtOH, benzene and 5:5:2 Et2O-isopentane-EtOH at 298 and 77掳K. Quantum yields were dependent on matrix viscosity and temperature Singlet-triplet splittings for the N-arylbenzamides, determined from the emission spectra, were small for 蟺,蟺* states (鈭?1500 cm-1). Phosphorescence maximum were blue-shifted relative to the fluorescence maximum Intersystem crossing efficiencies were consistent with S1 鈫?S0 radiationless decay. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application In Synthesis of 2-Phenylisoindolin-1-one).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Application In Synthesis of 2-Phenylisoindolin-1-one

Fang, Zhang et al. published their research in European Journal of Organic Chemistry in 2022 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. In addition to tryptophan, indigo, and indoleacetic acid, numerous compounds obtainable from plant or animal sources contain the indole molecular structure. It is used in perfumery and in making tryptophan, an essential amino acid, and indoleacetic acid (heteroauxin), a hormone that promotes the development of roots in plant cuttings.Safety of 2-Phenylisoindolin-1-one

A New Approach to Isoindolinones: Rhodium(III)-Catalyzed [3+2] Annulation Reactions of N-Methoxybenzamides with Bis(tosylamido)methane was written by Fang, Zhang;Shu, Sai;Zhou, Guanyu;Deng, Zefeng;Huang, Pengcheng;Li, Bao;Zhao, Yingsheng. And the article was included in European Journal of Organic Chemistry in 2022.Safety of 2-Phenylisoindolin-1-one This article mentions the following:

A new approach to the synthesis of isoindolinones I (R = H, Me, OMe, etc.; R¹ = Me, OPh, Cl, etc.; R² = Cl, Me, (cyclopropylmethyl)oxidanyl, etc.; R³ = H, Cl; R⁴ = H, 2-Me, 4-Br, etc.) via direct coupling of N-methoxybenzamides 2R-3R¹-4R²-5R³C₆HC(O)NHOMe and bis(tosylamido)methane (R⁴NH)₂CH₂ with rhodium(III) as catalyst has been developed. The reaction is performed under mild conditions without oxidant, and is compatible with various functional groups. Compared with the previously reported methods for constructing isoindolinone skeletons, this method involves a novel [3+2] cyclization, and affords a wide variety of isoindolinones I in moderate to excellent yields. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Safety of 2-Phenylisoindolin-1-one).

Yuan, Yu-Chao et al. published their research in Journal of Organic Chemistry in 2019 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Product Details of 5388-42-1

C-H Bond Alkylation of Cyclic Amides with Maleimides via a Site-Selective-Determining Six-Membered Ruthenacycle was written by Yuan, Yu-Chao;Goujon, Marion;Bruneau, Christian;Roisnel, Thierry;Gramage-Doria, Rafael. And the article was included in Journal of Organic Chemistry in 2019.Product Details of 5388-42-1 This article mentions the following:

The first example of a ruthenium-catalyzed C-H bond alkylation via six-membered ruthenacycles is presented. This is disclosed for the C-H bond alkylation of biol. relevant cyclic amides with maleimide derivatives The cyclic tertiary amide core acted as a directing group (DG) enabling formation of six-membered cycloruthenated species responsible for the control of the regio- and site selectivity of the reaction as well as the excellent functional group tolerance. Unexpectedly, cyclic amides were found to be better DGs than pyridine-containing ones or cyclic imides for this type of C-H bond functionalization. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Product Details of 5388-42-1).

Ludt, Robert E. et al. published their research in Journal of Organic Chemistry in 1971 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. Indole plays a fundamental role for QS in E. coli, being one of the signal molecules responsible for the transcription of a variety of genes (gabT, and tnaB ASTD). Application of 5388-42-1

Effect of tetramethylethlylenediamine on the metalation of N-methyl and N-phenylbenzylamine with n-butyllithium. Deuteration and electrophilic condensations of intermediate lithioamines. Cyclodehydrations to give N-substituted isoindolines was written by Ludt, Robert E.;Hauser, Charles R.. And the article was included in Journal of Organic Chemistry in 1971.Application of 5388-42-1 This article mentions the following:

PhCH2NHMe underwent dimetalation with BuLi-Me2NCH2CH2NMe2 (TMEDA) predominantly at the N and the o-benzyl positions as evidenced by deuteration studies. The intermediate o-LiC6H4CH2NMeLi was condensed with BzPh, BzH, cyclohexanone, BzMe, and BzEt. The resulting o-carbinolamines from the BzPh and BzH condensations underwent acid-catalyzed cyclodehydration to form N-methylisoindoline derivatives, while the ortho codensation products from the latter 3 ketones underwent acid-catalyzed linear dehydration reactions, rather than cyclodehydration to form isoindolines. N-Phenylbenzylamine was similarly dimetalated at the N and o-benzyl positions with TMEDA activated BuLi. o-Carbonyl addition reactions of the dilithio amine intermediate with CO2, BzPh, BzH, and 9-fluorenone resulted in an acid and o-carbinolamines, which were readily cyclodehydrated to N-phenylphthalimidine and N-phenylisoindoline derivatives In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Application of 5388-42-1).

Takahashi, Ichiro et al. published their research in Heterocycles in 2016 | CAS: 5388-42-1

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 5388-42-1

Application of the mild-condition phthalimidine synthesis with use of 1,2,3-1H-benzotriazole and 2-mercaptoethanol as dual synthetic auxiliaries. Effective synthesis of phthalimidines possessing a variety of substituents at 2-position was written by Takahashi, Ichiro;Kawakami, Teruki;Hirano, Etsushi;Kimino, Mako;Kamimura, Shigeki;Miwa, Takayuki;Tamura, Takanori;Tazaki, Ryo;Kitajima, Hidehiko;Hatanaka, Minoru;Isa, Kimio;Hosoi, Shinzo. And the article was included in Heterocycles in 2016.Reference of 5388-42-1 This article mentions the following:

Synthesis of 2-substituted phthalimidines (2,3-dihydroisoindol-1-one) I [R = t-Bu, C⁶H⁵, c-C⁶H¹¹, etc.] were described via Mannich type condensation reaction between o-phthalaldehyde with a variety of primary amines in the presence of excess 2-mercaptoethanol and 1,2,3-1H-benzotriazole as dual synthetic auxiliaries. In the experiment, the researchers used many compounds, for example, 2-Phenylisoindolin-1-one (cas: 5388-42-1Reference of 5388-42-1).

2-Phenylisoindolin-1-one (cas: 5388-42-1) belongs to indole derivatives. Indole, also called Benzopyrrole, a heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Reference of 5388-42-1