(-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID

Base Information

• Chemical Name: (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID
• CAS No.: 140860-51-1
• Molecular Formula: C8H6 Br N O
• Molecular Weight: 212.046
• Hs Code.: 2926909090
• European Community (EC) Number: 817-279-7
• DSSTox Substance ID: DTXSID00459074
• Nikkaji Number: J1.350.210B
• Wikidata: Q72446116
• Mol file: 140860-51-1.mol

Synonyms:(-)-(1S,4R)-GAMMA-HOMOCYCLOLEU-2-ENE

Chemical Property of (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID

Chemical Property:

• Melting Point: 139.3 °C
• Boiling Point: 312.8±27.0 °C(Predicted)
• PSA: 33.02000
• Density: 1.56
• LogP: 2.32938
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 210.96328
• Heavy Atom Count: 11
• Complexity: 174

Purity/Quality:

98%min ^*data from raw suppliers

2-bromo-4-methoxybenzonitrile ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=C(C=C1)C#N)Br

Technology Process of (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID

There total 8 articles about (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID 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: 79.0%

4-methoxybenzonitrile (874-90-8) → 2-bromo-4-methoxy benzonitrile (140860-51-1)

Guidance literature:

With N-Bromosuccinimide; palladium diacetate; toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 70 ℃; for 12h; Sealed tube;

DOI:10.1021/jo302765g

Reference yield: 64.0%

2-bromo-5-methoxy-benzaldehyde-oxime → 2-bromo-4-methoxy benzonitrile (140860-51-1)

Guidance literature:

With PEG-supported methyl N-(triethylammonium-sulfonyl)carbamate; In tetrahydrofuran; Heating;

Reference yield: 38.0%

3-methoxyphenyl bromide (2398-37-0) + (3,5-bis(trifluoromethyl)phenyl)(cyano)-l3-iodanyl trifluoromethanesulfonate → 2-bromo-4-methoxy benzonitrile (140860-51-1)

Guidance literature:

With iron(II) acetate; In 1,2-dichloro-ethane; at 70 ℃; for 48h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201309791

upstream raw materials:

diazomethane

2-bromo-4-hydroxybenzonitrile

2-bromo-5-methoxy-benzaldehyde

4-methoxybenzonitrile

Downstream raw materials:

4-methoxy-2-methylbenzonitrile

Refernces

• 1、 Shu, Zhibin,Ji, Wenzhi,Wang, Xi,Zhou, Yujing,Zhang, Yan,Wang, Jianbo. "Iron(II)-catalyzed direct cyanation of arenes with aryl(cyano)iodonium triflates". supporting information. p. 2186 - 2189. Retrieved 2014/03/21.
• 2、 Chao, Bo,Tong, Xian-Kun,Tang, Wei,Li, De-Wen,He, Pei-Lan,Garcia, Jean-Michel,Zeng, Li-Min,Gao, An-Hui,Yang, Li,Li, Jia,Nan, Fa-Jun,Jacobs, Michael,Altmeyer, Ralf,Zuo, Jian-Ping,Hu, You-Hong. "Discovery and optimization of 2,4-diaminoquinazoline derivatives as a new class of potent dengue virus inhibitors". experimental part. p. 3135 - 3143. Retrieved 2012/06/01.