2731-01-3

Basic information

• Product Name: (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole
• CAS NO: 2731-01-3
• Molecular Weight: 232.326
• Mol File: 2731-01-3.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole(2731-01-3)
• EPA Substance Registry System: (±)-5-methoxy-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]indole(2731-01-3)

Safety Data

• Hazardous Substances Data: 2731-01-3(Hazardous Substances Data)

Upstream product

• 143947-74-4 5-methoxy-1,3-dimethyl-3-(2-methylamino-ethyl)-indolin-2-one 
• 50-00-0 formaldehyd 
• 46479-70-3 (+/-)-5-methoxy-3a,8-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole 
• 874796-19-7 N-[4-methoxy-2-[(trimethylsilyl)ethynyl]phenyl]-N'-methylcarbodiimide 
• 874796-20-0 5-methoxy-1-methyl-3-(trimethylsilyl)pyrrolo[2,3-b]indol-2-one 
• 59908-57-5 5-methoxy-1,3-dimethyl-1H-indole-2-carboxylic acid 
• 61838-92-4 ethyl-5-methoxy-1,3-dimethyl-1H-indole-2-carboxylate 
• 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 

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 
• 70354-71-1 (+/-)-eseroline 

Relevant articles and documents

Photocatalytic Cascade Radical Cyclization Approach to Bioactive Indoline-Alkaloids over Donor-Acceptor Type Conjugated Microporous Polymer

Herein, we describe a visible-light-induced radical strategy for the 1,2-formylarylation of N-arylacrylamides via the C-H activation of 1,3-dioxolane using a carbazolic-cyano conjugated microporous polymer (CC-CMP) as a metal-free photocatalyst. This process provides an efficient and mild approach for constructing highly functionalized formyl-substituted oxindoles, which are valuable building blocks that allow rapid access to various important heterocycle-fused and spirocyclic indole alkaloids. Utilizing this strategy, bioactive alkaloids, such as (±)-desoxyeseroline, (±)-esermethole, and (±)-N-Me-coerulescine, have been concisely synthesized in up to 74% overall yield from low-cost acrylamides and 1,3-dioxolane. The overall yields of our approach are much higher than those of conventional multistep methods. Gram-scale syntheses of natural alkaloids have been demonstrated, highlighting the practical utility of this protocol. The use of CC-CMP photocatalysts, which are metal-free, flexible, stable, effective, and reusable, making this strategy appealing to advanced chemical manufacturing.

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.

Synthesis of C3-Methyl-Substituted Pyrroloindolines and Furoindolines via Cascade Dearomatization of Indole Derivatives with Methyl Iodide

A highly efficient method for constructing C3-methyl-substituted pyrroloindolines and furoindolines via cascade dearomatization reaction of indole derivatives with methyl iodide was developed. This protocol offers a direct approach to a wide range of C3 methyl substituted pyrroloindolines under mild conditions. The utility of this method was further demonstrated in the concise synthesis of (±)-esermethol.