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

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

• 1255909-60-4 tert-butyl (R)-1-(2-methylprop-1-en-1-yl)-1,2,3,4-tetrahydro-6H-azepino[5,4,3-cd]indole-6-carboxylate 
• 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 
• 52488-36-5 4-bromo-1H-indole 
• 303068-05-5 tert-butyl 4-bromo-3-(2-((tert-butoxycarbonyl)amino)ethyl)-1H-indole-1-carboxylate 
• 108061-74-1 2-(4-bromo-1H-indol-3-yl)ethan-1-amine 
• 303068-04-4 4-bromo-3-(2-nitroethenyl)-indole 
• 1255909-59-1 (7R)-1,6-di-Boc-auranthioclavine 
• 1542231-54-8 C₂₂H₂₄N₂O₂S 
• 1542231-52-6 C₂₃H₂₄N₂O₄S 
• 1542231-49-1 C₂₆H₃₀N₂O₄S 

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).

Intramolecular Fischer Indole Synthesis for the Direct Synthesis of 3,4-Fused Tricyclic Indole and Application to the Total Synthesis of (-)-Aurantioclavine

Aryl hydrazides with a ketone or aldehyde containing side chains linked to the meta-position of the aromatic ring undergo acid-promoted intramolecular Fischer indole synthesis to generate 3,4-fused tricyclic indoles. The preparative utility of this concep

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.

Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis

(-)-Aurantioclavine (1), which contains a characteristic seven-membered ring fused to an indole ring, belongs to the azepinoindole class of fungal clavine alkaloids. Here we show that starting from a 4-dimethylallyl-l-tryptophan precursor, a flavin adenine dinucleotide (FAD)-binding oxidase and a catalase-like heme-containing protein are involved in the biosynthesis of 1. The function of these two enzymes was characterized by heterologous expression, in vitro characterization, and deuterium labeling experiments.

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

Total synthesis of clavicipitic acid and aurantioclavine: Stereochemistry of clavicipitic acid revisited

The stereocontrolled total synthesis of clavicipitic acid and aurantioclavine from a common azepino[5,4,3-cd]-indole intermediate is reported. This key azepinoindole nucleus was constructed via a one-pot Heck/Boc-deprotection/aminocyclization process from

Total synthesis of (-)-aurantioclavine

Figure presented The concise total synthesis of (-)-aurantioclavine has been achieved by taking advantage of strategies for the asymmetric alkenylation of N-tert-butanesulfinyl imines. The enantiomerically pure natural product was prepared in 6 steps and 27% overall yield by using Rh-catalyzed addition of a N-methyliminodiacetic acid (MIDA) boronate and in 5 steps and 29% yield by employing a Grignard reagent addition sequence.

Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: Applications to the total synthesis of alkaloids

Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an aryne C-C insertion reaction in accessing complex polycyclic frameworks is also described.