9-Azabicyclo[4.2.1]non-2-ene-9-carboxylicacid, 2-acetyl-, 1,1-dimethylethyl ester, (1R)- (9CI)

Base Information

• Chemical Name: 9-Azabicyclo[4.2.1]non-2-ene-9-carboxylicacid, 2-acetyl-, 1,1-dimethylethyl ester, (1R)- (9CI)
• CAS No.: 90741-53-0
• Molecular Formula: C15H23 N O3
• Molecular Weight: 265.348
• Mol file: 90741-53-0.mol

Synonyms:(1R)-N-(t-Butoxycarbonyl)anatoxina

Chemical Property of 9-Azabicyclo[4.2.1]non-2-ene-9-carboxylicacid, 2-acetyl-, 1,1-dimethylethyl ester, (1R)- (9CI)

Chemical Property:

• Vapor Pressure: 6.94E-06mmHg at 25°C
• Boiling Point: 377°Cat760mmHg
• Flash Point: 181.8°C
• PSA: 46.61000
• Density: 1.098g/cm³
• LogP: 3.00160

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9-Azabicyclo[4.2.1]non-2-ene-9-carboxylicacid, 2-acetyl-, 1,1-dimethylethyl ester, (1R)- (9CI)

There total 65 articles about 9-Azabicyclo[4.2.1]non-2-ene-9-carboxylicacid, 2-acetyl-, 1,1-dimethylethyl ester, (1R)- (9CI) 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: 93.0%

tert-butyl (1R,6R)-2-ethynyl-9-azabicyclo[4.2.1]non-2-ene-9-carboxylat → (1R)-2-acetyl-9-(1-tert-butoxycarbonyl)-9-azobicyclo<4.2.1>-2-nonene (90741-53-0)

Guidance literature:

With boron trifluoride diethyl etherate; mercury(II) oxide; trichloroacetic acid; In methanol; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.tet.2018.04.057

Reference yield: 90.0%

tert-butyl (1R*,6R*)-2-ethynyl-9-azabicyclo[4.2.1]non-2-ene-9-carboxylate → t-butyl-1-(9-azabicyclo<4.2.1>-non-2-ene-2-yl)ethanone carbamate (90741-53-0,90821-08-2,92998-50-0)

Guidance literature:

With boron trifluoride diethyl etherate; mercury(II) oxide; trichloroacetic acid; In methanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201904002

Reference yield: 81.0%

9-(tert-butoxycarbonyl)-2-((Z)-1-(dimethyl-tert-butylsiloxy)ethylidene)-9-azabicyclo[4.2.1]nonane → t-butyl-1-(9-azabicyclo<4.2.1>-non-2-ene-2-yl)ethanone carbamate (90741-53-0,90821-08-2,92998-50-0)

Guidance literature:

With palladium diacetate; In acetonitrile; for 48h; Ambient temperature;

DOI:10.1016/0040-4020(96)00645-X

upstream raw materials:

chloro-trimethyl-silane

(1R)-2-β-acetyl-9-((tert-butyloxy)carbonyl)-9-azabicyclo<4.2.1>nonane

(1R,2RS)-9-(tert-butoxycarbonyl)-2-<(Z)-1-(dimethyl-tert-butylsilyloxy)ethylidene>-9-azabicyclo<4.2.1>nonane

(1R,6R)-2-[1-Trimethylsilanyloxy-eth-(E)-ylidene]-9-aza-bicyclo[4.2.1]nonane-9-carboxylic acid tert-butyl ester

Downstream raw materials:

(+/-)-anatoxin-a

(+/-)-Anatoxin A

(+)-anatoxin-a hydrochloride

(1R,6R)-9-Aza-bicyclo[4.2.1]non-2-ene-2,9-dicarboxylic acid 9-tert-butyl ester 2-methyl ester

Refernces

• 1、 Addante-Moya, Luis G.,Agulló, Consuelo,Qui?ones-Reyes, Guillermo,Mercader, Josep V.,Abad-Fuentes, Antonio,Abad-Somovilla, Antonio. "A unified approach to the synthesis of both enantiomers of anatoxin-a and homoanatoxin-a cyanotoxins". . p. 5022 - 5031. Retrieved 2018/05/04.
• 2、 Parsons, Philip J.,Camp, Nicholas P.,Underwood, J. Mark,Harvey, Darren M.. "Tandem reactions of anions: A short and efficient route to ±anatoxin-a". . p. 11637 - 11642. Retrieved 2007/10/03.