65166-97-4

Basic information

• Product Name: (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole
• Synonyms: esermethole
• CAS NO: 65166-97-4
• Molecular Formula: C₁₄H₂₀N₂O
• Molecular Weight: 232.3214
• Mol File: 65166-97-4.mol
• Article Data: 49

Chemical Properties

• Boiling Point: 348.1°C at 760 mmHg
• Flash Point: 103.8°C
• Density: 1.087g/cm³
• Vapor Pressure: 5.14E-05mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole(65166-97-4)
• EPA Substance Registry System: (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole(65166-97-4)

Safety Data

• Hazardous Substances Data: 65166-97-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "(3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole" is a complex organic molecule with a fused bicyclic ring structure. It consists of a pyrroloindole core with a methoxy group attached to the 5th carbon, and three methyl groups attached to the 1st, 3rd, and 8th carbons. (3aS,8aR)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole has potential pharmaceutical importance due to its structural novelty and the presence of a methoxy group, which can influence its biological activity. The unique arrangement of atoms in this molecule may give it interesting biological properties, making it a potential candidate for further pharmacological investigation.

Upstream product

• 139115-75-6 2-iodo-4-methoxy-N-methylaniline 
• 50-00-0 formaldehyd 
• 46479-70-3 (+/-)-5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 64085-52-5 5-bromo-2-iodo-aniline 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 157496-75-8 tert-butyl (2-iodo-4-methoxyphenyl)carbamate 
• 1426832-63-4 C₁₅H₂₁NO₃ 
• 128368-43-4 2-isopropenyl-4-methoxyaniline 
• 128368-44-5 (2-Isopropenyl-4-methoxy-phenyl)-carbamic acid methyl ester 
• 128368-45-6 [(2-Isopropenyl-4-methoxy-phenyl)-methoxycarbonyl-amino]-acetic acid methyl ester 
• 128368-46-7 [(2-Isopropenyl-4-methoxy-phenyl)-methoxycarbonyl-amino]-acetic acid 
• 128368-47-8 (2aS,7bR)-6-Methoxy-7b-methyl-2-oxo-1,2,2a,7b-tetrahydro-cyclobuta[b]indole-3-carboxylic acid methyl ester 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 35292-54-7 N-methyl-N-(p-methoxyphenyl)hydrazine 

Downstream Products

• 57-47-6 (+/-)-Physostigmine 
• 104069-12-7 (3aR,8aS)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 101246-66-6 phenserine 
• 29347-15-7 (+)-Eseroline 
• 104015-32-9 (3S)-1,3-dimethyl-3-<2'-(dimethylamino)ethyl>-5-hydroxyindoline 
• 57-47-6 Physostigmin 
• 139314-01-5 (3aS,cis)-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-5-yl-3,4-dihydro-2(1H)-isoquinolinecarboxylate 
• 70354-71-1 (+/-)-eseroline 
• 104015-30-7 (3S)-1,3-dimethyl-3-<2'-(dimethylamino)ethyl>-5-methoxyindoline 
• 469-22-7 eseroline 

Relevant articles and documents

Ethylene in organic synthesis: A new route to anticholenergic pyrrolidinoindolines, and other molecules with all carbon-quaternary centers via asymmetric hydrovinylation

The asymmetric hydrovinylation (1 mol % Ni-cat., 1 atm, ethylene, >98% ee) products from 1-methylenetetralines are readily converted into 3, 3-disubstituted oxindoles and subsequently to pyrrolidinoindolines. These hydrovinylation products are also useful for the syntheses of enantiopure benzomorphans.

Nickel-Catalyzed Enantioselective Carbamoyl Iodination: A Surrogate for Carbamoyl Iodides

This work reports the enantioselective formal transfer of a carbamoyl iodide across a 1,1-disubstituted styrene using Ni-catalysis. Employing an air-stable Ni(II) precatalyst and a commercially available chiral ligand ((S)-tBuPHOX), enantioenriched 3,3-disubstituted iodooxindoles were obtained in up to 90% yield and up to 97:3 e.r. This methodology was applied to the total synthesis of (-)-esermethole and (-)-phenserine.

The photocatalysis synthetic alkaloid (by machine translation)

The present invention provides a catalytic synthesis method of living beings, the alkaloid comprises indole fused ring class and indole spiro compound, the process is as follows: in order to nitrogen aryl acrylamide as raw materials in under the photocatalysis with peroxide synthesis 3 - acetal 2 - indole compound, obtained through hydrolysis 3 - formyl - 2 - indole compound, further reducing synthetic alkaloid, the method routes mild, efficiency is high-efficient. The reaction in the illumination can occur under the room temperature, mild condition, has better substrate versatility and functional group tolerant. (by machine translation)

Pd(0)-Catalyzed Chemoselective Deacylative Alkylations (DaA) of N-Acyl 2-Oxindoles: Total Syntheses of Pyrrolidino[2,3- b]indoline Alkaloids, (±)-Deoxyeseroline, and (±)-Esermethole

We report an efficient Pd(0)-catalyzed deacylative allylation of N-acyl 3-substituted 2-oxindoles via the coupling of in situ generated nucleophiles (3 and 4) with allyl electrophiles for the synthesis of a variety of 2-oxindoles with C3-quaternary centers. Gratifyingly, this alkylation process is found to be highly chemoselective in nature, where a C-C bond formation is completely predominant over a C-N bond formation. A variety of key intermediates were synthesized utilizing an aforementioned methodology.