| Identification | Back Directory | [Name]
[6aS,(+)]-9α-Ethenyl-2,6,6aα,7,8,9,10,10aβ-octahydro-10α-isocyano-6,6,9-trimethylnaphtho[1,2,3-cd]indole | [CAS]
106928-30-7 | [Synonyms]
Hapalindole U
Dechlorohapalindol A-10a-epimer
[6aS,(+)]-9α-Ethenyl-2,6,6aα,7,8,9,10,10aβ-octahydro-10α-isocyano-6,6,9-trimethylnaphth[1,2,3-cd]indole
[6aS,(+)]-9α-Ethenyl-2,6,6aα,7,8,9,10,10aβ-octahydro-10α-isocyano-6,6,9-trimethylnaphtho[1,2,3-cd]indole | [Molecular Formula]
C21H24N2 | [MOL File]
106928-30-7.mol | [Molecular Weight]
304.429 |
| Hazard Information | Back Directory | [Definition]
ChEBI: Hapalindole U is a hapalindole that is hapalindole H in which the octahydronaphthalene ring junction carbons both have S configuration instead of R. It is an isocyanide, an organic heterotetracyclic compound and a hapalindole. | [Preparation]
To a cooled ( 20 C°) solution of the formamide (6.5 mg) in pyridine (0.4 mL) under Ar atmosphere was added phosphoryl chloride (11 mL) and the mixture was stirred at the same temperature for 40 min. Addition of saturated aq. NaHCO3, extraction with 10% MeOH/ CH2Cl2, standard work-up, and PTLC (hexane/EtOAc, 4:1) afforded (±)-hapalindole U 1629 (4.5 mg, 73%) as colorless needles; mp 240–242 C° (CH2Cl2/hexane).
During the synthesis and evaluation of a series of arachidonate epoxy inhibitors, 1631 was prepared in 85% yield by dehydration of the formamide 1630 with phosphoryl chloride. |
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