22793-63-1

Basic information

• Product Name: 6,7,8,9,10,11-HEXAHYDRO-5H-CYCLOOCTA[B]INDOLE
• Synonyms: 6,7,8,9,10,11-HEXAHYDRO-5H-CYCLOOCTA[B]INDOLE;INDOLO(2,3-B)CYCLOOCTENE;2,3-cyclooctenoindole;6,7,8,9,10,11-HEXAHYDROCYCLOOCT[B]INDOLE, 97%;5H-Cyclooct[b]indole, 6,7,8,9,10,11-hexahydro-
• CAS NO: 22793-63-1
• Molecular Formula: C₁₄H₁₇N
• Molecular Weight: 199.29
• Mol File: 22793-63-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: 57 °C
• Boiling Point: 355.5°Cat760mmHg
• Flash Point: 154.5°C
• Appearance: /
• Density: 1.082g/cm³
• Vapor Pressure: 6.38E-05mmHg at 25°C
• Refractive Index: 1.618
• PKA: 17.84±0.20(Predicted)
• CAS DataBase Reference: 6,7,8,9,10,11-HEXAHYDRO-5H-CYCLOOCTA[B]INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7,8,9,10,11-HEXAHYDRO-5H-CYCLOOCTA[B]INDOLE(22793-63-1)
• EPA Substance Registry System: 6,7,8,9,10,11-HEXAHYDRO-5H-CYCLOOCTA[B]INDOLE(22793-63-1)

Safety Data

• Hazardous Substances Data: 22793-63-1(Hazardous Substances Data)

Usage

General Description

6,7,8,9,10,11-HEXAHYDRO-5H-CYCLOOCTA[B]INDOLE, also known as harmine, is a naturally occurring compound found in a variety of plants, including certain species of the Banisteriopsis and Peganum genera. It belongs to the family of beta-carboline alkaloids and has been traditionally used in indigenous medicine and religious rituals in South America and the Middle East. It has been studied for its potential psychoactive and therapeutic effects, including its ability to inhibit the activity of certain enzymes and receptors in the brain. Harmine has also shown promise in research for its potential anti-inflammatory, antidepressant, and anti-cancer properties, although further studies are needed to fully understand its mechanisms of action and potential medical applications.

InChI:InChI=1/C14H17N/c1-2-4-9-13-11(7-3-1)12-8-5-6-10-14(12)15-13/h5-6,8,10,15H,1-4,7,9H2

Upstream product

• 502-49-8 cycloactanone 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 1556-09-8 cyclooctyl bromide 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 201230-82-2 carbon monoxide 
• 628-92-2 Cycloheptene 
• 104563-27-1 N-cycloheptylmethylene-N'-phenylhydrazine 
• 95-51-2 o-chloroaniline 
• 106347-55-1 N-Cyclooctylidene-N'-phenyl-hydrazine 
• 77118-64-0 4-(2,3,4,5,6,7-Hexahydro-1H-cyclooctindol-7-yl)-3-buten-2-on 
• 1227476-15-4 Azobenzene 
• 190788-59-1 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene 
• 1402424-10-5 2-allyl-3-(propa-1,2-dienyl)-1-tosyl-1H-indole 

Downstream Products

• 5560-72-5 iprindole 
• 130872-88-7 C₂₁H₂₀Cl₂N₂O₂ 
• 130872-91-2 C₂₄H₂₈N₂O₂ 
• 82237-74-9 11a-(2-Nitro-phenylsulfanyl)-7,8,9,10,11,11a-hexahydro-6H-cycloocta[b]indole 

Relevant articles and documents

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Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para-quinone Methides

Catalytic asymmetric N-alkylation of indoles and carbazoles represents a family of important but underdeveloped reactions. Herein, we describe a new organocatalytic strategy in which in situ generated aza-para-quinone methides are employed as the alkylating reagent. With the proper choice of a chiral phosphoric acid and an N-protective group, the intermolecular C?N bond formation with various indole and carbazole nucleophiles proceeded efficiently under mild conditions with excellent enantioselectivity and functional-group compatibility. Control experiments and kinetic studies provided important insight into the reaction mechanism.

A Convenient Modification of the Fischer Indole Synthesis with a Solid Acid

(Chemical Equation Presented). A new one-pot version of the titled reaction involves heating a mixture of a carbonyl compound, a phenylhydrazine, and the cation exchange resin Amberlite IR 120 in refluxing ethanol. A variety of enolizable aldehydes, and ketones and several substituted phenylhydrazines could thus be converted to the corresponding indoles in excellent yields (70-88%). Reaction times were typically 6-10 h, with the resin being then filtered off and the product isolated after minimal workup.