15889-93-7

Basic information

• Product Name: 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline
• Synonyms: 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline;Crispine A
• CAS NO: 15889-93-7
• Molecular Formula: C₁₄H₁₉NO₂
• Molecular Weight: 233.30616
• Product Categories: Amines, Aromatics, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 15889-93-7.mol
• Article Data: 38

Chemical Properties

• Melting Point: 87-88 °C
• Boiling Point: 110-120 °C(Press: 0.02 Torr)
• Appearance: /
• Density: 1.15±0.1 g/cm3(Predicted)
• PKA: 8.31±0.20(Predicted)
• CAS DataBase Reference: 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline(15889-93-7)
• EPA Substance Registry System: 1,2,3,5,6,10b-Hexahydro-8,9-diMethoxypyrrolo[2,1-a]isoquinoline(15889-93-7)

Safety Data

• Hazardous Substances Data: 15889-93-7(Hazardous Substances Data)

Usage

Uses

Crispine A is a tricyclic indolizidine alkaloid as potent α2-adrenoceptor antagonist.

Upstream product

• 1158959-68-2 8,9-dimethoxy-3,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinoline 
• 50548-58-8 methyl 4-<2-(2-acetamidoethyl)-4,5-dimethoxyphenyl>-4-oxobutyrate 
• 848087-02-5 6,7-dimethoxy-1-(3-trimethylsilylprop-2-ynyl)-1,2,3,4-tetrahydroisoquinoline 
• 3382-18-1 6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 67544-77-8 (3,4-Dimethoxyphenyl)acetic acid-N-hydroxysuccinimide ester 
• 10313-60-7 3,4-dimethoxyphenylacetyl chloride 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 930296-80-3 N-(4,4-diethoxybutyl)-2-(3,4-dimethoxyphenyl)acetamide 
• 930296-79-0 1-{[3,4-bis(methyloxy)phenyl]acetyl}-2-(ethyloxy)pyrrolidine 
• 96165-86-5 8,9-dimethoxy-2,3,5,6-tetrahydropyrrolo<2,1-a>isoquinoline 
• 104058-44-8 8,9-bis(methyloxy)-2,3,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-5(1H)-one 
• 1210-57-7 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 107-02-8 acrolein 
• 96567-31-6 5,6-Dihydro-8,9-dimethoxypyrrolo<2,1-a>isochinolin 

Downstream Products

• 1345019-56-8 C₁₀H₁₅OPS*C₁₄H₁₉NO₂ 
• 1345019-54-6 C₁₀H₁₅OPS*C₁₄H₁₉NO₂ 

Relevant articles and documents

Direct C-H Allylation of N-Acyl/Sulfonyl Tetrahydroisoquinolines and Analogues

A highly efficient direct C-H allylation reaction at the α position of N-acyl/sulfonyl tetrahydroisoquinolines under mild conditions was developed. The reaction was also suitable for allylation of other protected nitrogen-containing heterocycles. Several

Total synthesis of the antitumor active pyrrolo[2,1-a]isoquinoline alkaloid (±)-crispine a

Addition of a propargyl Grignard reagent to 3,4-dihydro-6,7- dimethoxyisoquinoline, silver(I)-promoted oxidative cyclization, and chemoselective hydrogenation of the pyrrole ring provide a simple three-step route to the antitumor active pyrrolo[2,1-a]isoquinoline alkaloid (±)-crispine A.

Direct Arylation of Distal and Proximal C(sp3)-H Bonds of t-Amines with Aryl Diazonium Tetrafluoroborates via Photoredox Catalysis

A visible light-mediated arylation protocol for t-amines has been reported through the coupling of γ- and α-amino alkyl radicals with different aryl diazonium salts using Ru(bpy)3Cl2·6H2O as a photocatalyst. Structurally different 9-aryl-9,10-dihydroacridine, 1-aryl tetrahydroisoquinoline, hexahydropyrrolo[2,1-a]isoquinoline, and hexahydro-2H-pyrido[2,1-a]isoquinoline frameworks with different substitution patterns have been synthesized in good yield using this methodology.

Tf2O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides

Ten types of Tf2O/TTBP-mediated amide transformation reactions were investigated. The results showed that compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.), TTBP can serve as an alternative amide activation system for the direct transformation of both secondary and tertiary amides. For most surveyed examples, higher or comparable yields were generally obtained. In addition, Tf2O/TTBP combination was used to promote the condensation reactions of 2-(tert-butyldimethylsilyloxy)furan (TBSOF) with both tertiary and secondary amides, the one-pot reductive Bischler-Napieralski-type reaction of tertiary lactams, and Movassaghi and Hill's modern version of the Bischler-Napieralski reaction. The value of the Tf2O/TTBP-based methodology was further demonstrated by the concise and high-yielding syntheses of several natural products.

Synthetic method of tetrahydroisoquino ring compound and tetrahydro-beta-carbo ring compound

The invention provides a synthetic method of a tetrahydroisoquino ring compound and a tetrahydro-beta-carbo ring compound, and belongs to the technical field of synthesis. According to the method forsynthesizing the tetrahydroisoquino and the tetrahydro-b