1,2,3,4-Tetrahydrocyclopenta[b]indole

Base Information

• Chemical Name: 1,2,3,4-Tetrahydrocyclopenta[b]indole
• CAS No.: 2047-91-8
• Molecular Formula: C11H11N
• Molecular Weight: 157.215
• Hs Code.: 2933990090
• European Community (EC) Number: 626-055-6
• NSC Number: 112674
• DSSTox Substance ID: DTXSID10296917
• Nikkaji Number: J377.249G,J3.171.754J
• Wikidata: Q72505423
• Mol file: 2047-91-8.mol

Synonyms:1,2,3,4-tetrahydro-cyclopenta(b)indole

Chemical Property of 1,2,3,4-Tetrahydrocyclopenta[b]indole

Chemical Property:

• Vapor Pressure: 0.00195mmHg at 25°C
• Melting Point: 100.5-105.5 °C(lit.)
• Refractive Index: 1.701
• Boiling Point: 300.9 °C at 760 mmHg
• PKA: 17.83±0.20(Predicted)
• Flash Point: 130.4 °C
• PSA: 15.79000
• Density: 1.2 g/cm³
• LogP: 2.65660
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 157.089149355
• Heavy Atom Count: 12
• Complexity: 178

Purity/Quality:

98%, ^*data from raw suppliers

1,2,3,4-Tetrahydrocyclopent[b] indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2=C(C1)NC3=CC=CC=C23
• Uses: ? ;Reactant for thionium species-mediated functionalization at the 2α-position of indoles1? ;Reactant for preparation of tetramethylpiperidine-1-oxoammonium salts as oxidants2 1,2,3,4-Tetrahydrocyclopent[b]indole is used in the synthesis of BACE inhibitors. Also used to synthesize benzazocinecarboxylic acids as potential antiinflammatory agents. Reactant for thionium species-mediated functionalization at the 2α-position of indolesReactant for preparation of tetramethylpiperidine-1-oxoammonium salts as oxidants

Technology Process of 1,2,3,4-Tetrahydrocyclopenta[b]indole

There total 41 articles about 1,2,3,4-Tetrahydrocyclopenta[b]indole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(3aS,8bR)-2,3,3a,4-Tetrahydro-1H-cyclopenta[b]indol-8b-ol (78839-81-3) → 2,3-dihydro-1H-cyclopentindole (2047-91-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1.75h;

DOI:10.1016/S0040-4020(01)88618-X

Reference yield: 98.0%

C11H11N3 (1279722-86-9) → 2,3-dihydro-1H-cyclopentindole (2047-91-8)

Guidance literature:

With rhodium (II) octanoate dimer; In 1,2-dichloro-ethane; at 70 ℃; for 16h; Inert atmosphere; Molecular sieve;

DOI:10.1002/anie.201006917

Reference yield: 97.0%

phenylhydrazine hydrochloride (59-88-1) + cyclopentanone (120-92-3) → 2,3-dihydro-1H-cyclopentindole (2047-91-8)

Guidance literature:

With L-(+)-tartaric acid-urea melt; at 70 ℃; for 0.5h;

DOI:10.1021/ol302034r

upstream raw materials:

diethyl ether

cyclopentanone phenylhydrazone

8b-methylsulfanyl-1,2,3,8b-tetrahydro-cyclopenta[b]indole

(3aS,8bR)-2,3,3a,4-Tetrahydro-1H-cyclopenta[b]indol-8b-ol

Downstream raw materials:

2-(2-benzoylamino-2-methoxycarbonylethyl)-6,10b-dihydro-5a,10b-propano-5aH-<1,4>benzodioxino<2,3-b>indole

8b-(2-Nitro-phenylsulfanyl)-1,2,3,8b-tetrahydro-cyclopenta[b]indole

1,4-dihydrocyclopenta[b]indol-3(2H)-one

1,2,3,4-tetrahydrocyclopentindol-1-one

Refernces

• 1、 Welmaker, Gregory S.,Sabalski, Joan E.. "A process for the preparation of 1,2,3,4,8,9,10,10a-octahydro-7bH- cyclopenta[b][1,4]diazepino[6,7,1-hi]indole". . p. 4851 - 4854. Retrieved 2004.
• 2、 Misal Castro, Luis C.,Sultan, Ibrahim,Nishi, Kohei,Tsurugi, Hayato,Mashima, Kazushi. "Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst". . p. 3287 - 3299. Retrieved 2021/03/01.
• 3、 Yang, Ping,Xu, Ren-Qi,Zheng, Chao,You, Shu-Li. "Pd-Catalyzed Dearomatization of Indole Derivatives via Intermolecular Heck Reactions?". supporting information. p. 235 - 241. Retrieved 2020/01/28.