(1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one

Base Information

• Chemical Name: (1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one
• CAS No.: 130931-83-8
• Molecular Formula: C6H7NO
• Molecular Weight: 109.128
• Hs Code.: 2933790090
• European Community (EC) Number: 627-840-6
• DSSTox Substance ID: DTXSID401336090
• Nikkaji Number: J724.494K
• Wikidata: Q6619630
• Wikipedia: Vince_lactam
• Mol file: 130931-83-8.mol

Synonyms:130931-83-8;(1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one;(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one;vince lactam;(1R,4S)-3-Azabicyclo[2.2.1]hept-5-en-2-one;(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one;2-Azabicyclo[2.2.1]hept-5-en-3-one, (1S,4R)-;(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one;(1S,4R)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one;MFCD00211275;(+)-Vince lactam;(1S, 4R)-2-Azabicyclo[2.2.1]hept-5-en-3-one;SCHEMBL1192745;DDUFYKNOXPZZIW-CRCLSJGQSA-N;DTXSID401336090;BCP07500;AKOS015924575;CS-W001398;AS-39359;2-Azabicyclo[2.2.1]hept-5-en-3-one, 98%;A806169;(1S,4R)-3-Oxo-2-azabicyclo[2.2.1]hept-5-ene;J-650393;Q6619630;W-205333;(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one, >=98%;(1S,4R)-2-Azabicyclo[2.2.1]hept-5-en-3-one;66Y

Chemical Property of (1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one

Chemical Property:

• Appearance/Colour: off-white to beige crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 94-97 °C(lit.)
• Refractive Index: 1.546
• Boiling Point: 319.302 °C at 760 mmHg
• PKA: 15.48±0.20(Predicted)
• Flash Point: 167.131 °C
• PSA: 29.10000
• Density: 1.199 g/cm³
• LogP: 0.38970
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 109.052763847
• Heavy Atom Count: 8
• Complexity: 162

Purity/Quality:

99.9% ^*data from raw suppliers

(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2C=CC1NC2=O
• Isomeric SMILES: C1[C@@H]2C=C[C@H]1NC2=O
• Uses: This lactam and its antipode are precursors to the enantiomers of the carbocyclic nucleoside carbovir. It has been demonstrated that (-)-carbovir is a potent inhibitor of HIV-1 and based on clinical trials it could become an alternative to AZT. AZT is a trademark of The Wellcome Foundation Ltd.

Technology Process of (1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one

There total 22 articles about (1S,4R)-2-azabicyclo[2.2.1]hept-5-en-3-one 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: 95.0%

(1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one (157810-20-3) → (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one (130931-83-8)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2016.06.019

Reference yield: 48.0%

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one (49805-30-3) → (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one (130931-83-8)

Guidance literature:

With resin-supported recombinant Candida antarctica lipase B; water; In tert-butyl methyl ether; at 60 ℃; for 102h; enantioselective reaction;

DOI:10.1016/j.tet.2010.03.030

Reference yield: 46.0%

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one (49805-30-3) → (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one (130931-83-8) + (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid (102579-71-5,102579-72-6,102679-78-7,134003-04-6,134234-04-1)

Guidance literature:

With lipase B from Candida antarctica; In water; isopropyl alcohol; at 60 ℃; for 4h; stereospecific reaction; Enzymatic reaction;

DOI:10.1002/ejoc.200800723

upstream raw materials:

2-azabicyclo[2.2.1.]hept-5-en-3-one

(1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one

(1S,4R)-2-[(4-methoxyphenyl)methyl]-2-azabicyclo[2.2.1]hept-5-en-3-one

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one

Downstream raw materials:

(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Refernces

• 1、 Nakano, Hiroto,Okuyama, Yuko,Iwasa, Kazuto,Hongo, Hiroshi. "A Facile Lipase-Catalyzed Resolution of 2-Azabicyclohept-5-en-3-ones". . p. 1155 - 1156. Retrieved 1994.
• 2、 Li, Hongxia,Zhu, Shaozhou,Zheng, Guojun. "Promiscuous (+)-γ-lactamase activity of an amidase from nitrile hydratase pathway for efficient synthesis of carbocyclic nucleosides intermediate". . p. 1071 - 1076. Retrieved 2018.
• 3、 -. "Chemical preparation method of 2-azabicyclo [2.2.1] hept-5-ene-3-one with optical activity". . . Retrieved 2020/05/08.
• 4、 Tanaka, Koichi,Muraoka, Toshihide,Otubo, Yasuhiro,Takahashi, Hiroki,Ohnishi, Atsushi. "HPLC enantioseparation on a homochiral MOF-silica composite as a novel chiral stationary phase". . p. 21293 - 21301. Retrieved 2016/03/08.