cis-3-azabicyclo[3,3,0]oct-2-ene

Base Information

• Chemical Name: cis-3-azabicyclo[3,3,0]oct-2-ene
• CAS No.: 1227703-21-0
• Molecular Formula: C7H11N
• Molecular Weight: 109.16894
• Mol file: 1227703-21-0.mol

Synonyms:cis-3-azabicyclo[3,3,0]oct-2-ene

Chemical Property of cis-3-azabicyclo[3,3,0]oct-2-ene

Chemical Property:

• PSA: 12.36000
• LogP: 0.92270

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-3-azabicyclo[3,3,0]oct-2-ene

There total 27 articles about cis-3-azabicyclo[3,3,0]oct-2-ene 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: 97.5%

octahydrocyclopenta[c]pyrrole (1468-87-7,5661-03-0,10268-00-5) → 3-azabicyclo-[3,3,0]oct-2-ene (1227703-21-0)

Guidance literature:

octahydrocyclopenta[c]pyrrole; With sodium hypochlorite; In water; at 0 - 15 ℃; for 6h;

With tetra(n-butyl)ammonium hydroxide; potassium hydroxide; In water; at 30 - 50 ℃; for 12h;

Reference yield: 85.0%

(3aR,6aS)-octahydrocyclopenta[c]pyrrole (1037834-39-1) → (3aS,6aR)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrrole (1205676-33-0,1227703-21-0)

Guidance literature:

With monoamine oxidase N from D₅ E_.Coli; at 37 ℃; pH=8; optical yield given as %ee; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/anie.201001592

Reference yield: 78.0%

(3aR,6aS)-octahydrocyclopenta[c]pyrrole (1037834-39-1) → (3aR,6aS)-1,3a,4,5,6,6a-hexahydrocyclopenta[c]pyrrole (1227703-21-0)

Guidance literature:

(3aR,6aS)-octahydrocyclopenta[c]pyrrole; With sodium hypochlorite; In tert-butyl methyl ether; water; at 0 ℃; for 3h; Inert atmosphere;

With tetrabutylammomium bromide; sodium hydroxide; In tert-butyl methyl ether; water; at 50 ℃; for 6h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c00387

upstream raw materials:

N-chloro-3-azabicyclo[3.3.0]octane

octahydrocyclopentane[c]pyrrole hydrochloride

octahydrocyclopenta[c]pyrrole

(3aR,6aS)-octahydrocyclopenta[c]pyrrole hydrochloride

Downstream raw materials:

C₈H₁₂N₂

C₁₉H₂₆N₂O₂

C₁₈H₂₄N₂O₂

C₁₇H₂₂N₂O₂

Refernces

• 1、 Liu, Lin-Wei,Wang, Fei-Ying,Tian, Fang,Peng, Lin,Wang, Li-Xin. "An Improved and Enantioselective Preparation of the Telaprevir Bicyclic [3.3.0] Proline Intermediate and Reuse of Unwanted Enantiomer". . p. 320 - 324. Retrieved 2016.
• 2、 Elkhatib,Peyrot,Scharff,Delalu. "Kinetics of dehydrohalogenation of N-chloro-3-azabicyclo[3,3,0]octane in alkaline medium. NMR and ES/MS evidence of the dimerization of 3-azabicyclo[3,3,0]oct-2-ene". . p. 129 - 136. Retrieved 1998.
• 3、 Kim, Jae Hyun,Paul, Anirudra,Ghiviriga, Ion,Seidel, Daniel. "α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines". supporting information. p. 797 - 801. Retrieved 2021/02/06.
• 4、 Valles, Daniel A.,Dutta, Subhradeep,Paul, Anirudra,Abboud, Khalil A.,Ghiviriga, Ion,Seidel, Daniel. "α,α′-C-H Bond Difunctionalization of Unprotected Alicyclic Amines". supporting information. p. 6367 - 6371. Retrieved 2021/08/18.