80152-02-9

Basic information

• Product Name: 1H-Azepino(5,4,3-cd)indole, 3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl) -, (-)-
• Synonyms: 1H-Azepino(5,4,3-cd)indole, 3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl) -, (-)-
• CAS NO: 80152-02-9
• Molecular Formula: C15H18 N2
• Molecular Weight: 226.32
• Mol File: 80152-02-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 405.3°C at 760 mmHg
• Flash Point: 198.9°C
• Appearance: /
• Density: 1.149g/cm³
• Vapor Pressure: 8.83E-07mmHg at 25°C
• Refractive Index: 1.678
• CAS DataBase Reference: 1H-Azepino(5,4,3-cd)indole, 3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl) -, (-)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Azepino(5,4,3-cd)indole, 3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl) -, (-)-(80152-02-9)
• EPA Substance Registry System: 1H-Azepino(5,4,3-cd)indole, 3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl) -, (-)-(80152-02-9)

Safety Data

• Hazardous Substances Data: 80152-02-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 33, p. 2162, 1985 DOI: 10.1248/cpb.33.2162

InChI:InChI=1/C15H18N2/c1-10(2)8-14-12-4-3-5-13-15(12)11(9-17-13)6-7-16-14/h3-5,8-9,14,16-17H,6-7H2,1-2H3

Upstream product

• 1070913-15-3 C₂₂H₂₄N₂O₂S 
• 29702-35-0 (S)-2-amino-3-(4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl)propanoic acid 
• 33062-26-9 (-)-trans-clavicipitic acid 
• 1542231-54-8 C₂₂H₂₄N₂O₂S 
• 1542231-52-6 C₂₃H₂₄N₂O₄S 
• 1542231-49-1 C₂₆H₃₀N₂O₄S 
• 1542231-28-6 C₁₂H₁₈INO₄Si 
• 197243-48-4 2-iodo-3-nitrophenol 
• 1070913-00-6 C₂₀H₂₃NO₄S 
• 1070913-14-2 C₂₈H₂₉N₃O₇S₂ 
• 1070913-10-8 C₂₈H₂₇N₃O₆S₂ 
• 1070913-08-4 C₂₈H₂₇N₃O₆S₂ 

Relevant articles and documents

Iridium-catalyzed enantioselective synthesis of (-)- and (+)-aurantioclavine

A new protocol for generating indoleazepine 9 via an Ir-catalyzed intramolecularly asymmetric amination of secondary allylic alcohol 5 in the presence of Carreira ligand (10) and Sc(OTf)3 is described. This methodology has been exploited in the facile synthesis of natural (-)-aurantioclavine (1), a biosynthetical precursor of communesins, and its unnatural enantiomer (+)-aurantioclavine (ent-1).

Asymmetric synthesis of (-)-aurantioclavine via palladium-catalyzed intramolecular allylic amination

The total synthesis of (-)-aurantioclavine (1) was accomplished based on an intramolecular asymmetric amination of allyl carbonate 3 containing a p-tosylamide group. The reaction using tris(dibenzylideneacetone)dipalladium(0), tBu-phosphinooxazoline, and Bu4NCl in CH2Cl2 gave azepane 2 in 77% yield with 95% enantiomeric excess. The obtained azepane 2 was also converted to a substructure of communesin F.

Confirmation of the absolute configuration of (-)-aurantioclavine

We confirm our previous assignment of the absolute configuration of (-)-aurantioclavine as 7R by crystallographically characterizing an advanced 3-bromoindole intermediate reported in our previous synthesis. This analysis also provides additional support