61302-92-9

Basic information

• Product Name: (13aS)-2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline
• CAS NO: 61302-92-9
• Molecular Formula: C₂₄H₂₇NO₄
• Molecular Weight: 393.4755
• Mol File: 61302-92-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 559.9°C at 760 mmHg
• Flash Point: 160.5°C
• Density: 1.26g/cm³
• Vapor Pressure: 1.44E-12mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: (13aS)-2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (13aS)-2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline(61302-92-9)
• EPA Substance Registry System: (13aS)-2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline(61302-92-9)

Safety Data

• Hazardous Substances Data: 61302-92-9(Hazardous Substances Data)

Usage

Description

(13aS)-2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline is a complex organic compound with a bicyclic structure. It is classified as a dibenzo[f,h]pyrrolo[1,2-b]isoquinoline derivative and contains four methoxy groups. (13aS)-2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline is a type of alkaloid, which are organic compounds found in plants and exhibit various biological activities. Its unique structural features and potential pharmacological properties make it a promising candidate for research in medicinal chemistry.

Uses

Used in Medicinal Chemistry:
(13aS)-2,3,5,6-tetramethoxy-9,11,12,13,13a,14-hexahydrodibenzo[f,h]pyrrolo[1,2-b]isoquinoline is used as a research compound in medicinal chemistry for its potential therapeutic applications and biological effects. Its unique structure and properties may offer insights into the development of new drugs and treatments.

Upstream product

• 50-00-0 formaldehyd 
• 40972-86-9 (2,3-dimethoxyphenyl)boronic acid 
• 89978-46-1 4-bromo-5-iodoveratrole 
• 1260216-15-6 (R)-7-(2',3',4,5-tetramethoxy-[1,1'-biphenyl]-2-yl)-1,2,3,5,8,8a-hexahydroindolizine 
• 1260216-09-8 2'-bromo-2,3,4',5'-tetramethoxy-1,1'-biphenyl 
• 621-59-0 isovanillin 
• 2859-78-1 4-Bromoveratrole 
• 2973-58-2 2-bromoisovanillin 
• 1588418-55-6 C₂₀H₂₀O₅ 
• 1588418-54-5 C₂₂H₂₄O₆ 
• 1588418-53-4 C₂₂H₂₄O₆ 
• 1588418-52-3 C₁₇H₁₉BrO₄ 
• 1588418-51-2 2-(3,4-dimethoxyphenyl)-3,4-dimethoxybenzyl alcohol 
• 85010-22-6 2-(3,4-dimethoxyphenyl)-3,4-dimethoxybenzaldehyde 

Relevant articles and documents

Modular Syntheses of Phenanthroindolizidine Natural Products

A highly concise strategy for the total synthesis of phenanthroindolizidines was developed. The one-pot iterative Suzuki-Miyaura reaction of aryl boronic acids with ortho-bromoaryl N-methyliminodiacetate (MIDA) boronate followed by a second Suzuki-Miyaura reaction with a suitable pyridyl bromide provided ortho-aza-terphenyls. Subsequent saturation of the triple bond, treatment with mesyl chloride, and reduction of the resulting dihydroindolizidinium ring afforded the hexahydroindolizines. A final vanadium-catalyzed oxidative electrocyclization provided the desired alkaloids in only three column-separation operations.

Synthesis of tylocrebrine and related phenanthroindolizidines by VOF 3-mediated oxidative aryl-alkene coupling

A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF3-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

Total synthesis of (S)-(+)-tylophorine via enantioselective intramolecular alkene carboamination

(Chemical Equation Presented) The enantioselective synthesis of (S)-(+)-tylophorine, a potent cancer cell growth inhibitor, has been accomplished in eight steps from commercially available 3,4-dimethoxybenzyl alcohol. A copper (II)-catalyzed enantioselective intramolecular alkene carboanimation was employed as the key step to construct the chiral indolizidine ring.