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

Base Information

• Chemical Name: (1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one
• CAS No.: 79200-56-9
• Molecular Formula: C6H7NO
• Molecular Weight: 109.128
• Hs Code.: 29337900
• European Community (EC) Number: 418-530-1,616-668-7,627-840-6
• DSSTox Substance ID: DTXSID10369337
• Nikkaji Number: J406.685E
• Wikidata: Q72444172
• Mol file: 79200-56-9.mol

Synonyms:79200-56-9;(1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one;(1R)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one;(1S,4R)-3-azabicyclo[2.2.1]hept-5-en-2-one;2-Azabicyclo[2.2.1]hept-5-en-3-one, (1R,4S)-;EC 418-530-1;(1R,4S)-2-Azabicyclo(2.2.1)hept-5-en-3-one;(1~{s},4~{r})-3-Azabicyclo[2.2.1]hept-5-En-2-One;(+/-)-2-Azabicyclo[2.2.1]hept-5-en-3-one;MFCD00213364;(-)-Vince Lactam;MFCD00211274;4-Amino-2-cyclopentene-1-carboxylic acid lactam;(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one;SCHEMBL419989;((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one;DTXSID10369337;DDUFYKNOXPZZIW-UHNVWZDZSA-N;AKOS006346791;AKOS016016507;AC-6113;CS-W009267;GS-4091;(1S,4R)-3-Azanorborna-5-ene-2-one;AM20080220;EN300-6744251;A839614;(1R, 4S)-2-azabicyclo[2.2.1]hept-5-en-3-one;(1R,4S)-3-Oxo-2-azabicyclo[2.2.1]hept-5-ene;rac-(1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one;(1R, 4S)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one;(1R)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one, >=98%;(4R)-3-azabicyclo[2.2.1]hept-5-en-2-one;66Z

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

Chemical Property:

• Appearance/Colour: Off-white to beige crystals or crystalline powder
• Vapor Pressure: 0.000342mmHg at 25°C
• Melting Point: 94-97 °C(lit.)
• Refractive Index: 1.545
• Boiling Point: 319.302 °C at 760 mmHg
• PKA: 15.48±0.20(Predicted)
• Flash Point: 167.131 °C
• PSA: 29.10000
• Density: 1.198 g/cm³
• LogP: 0.38970
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• 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% ^*data from raw suppliers

(1R)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41-43
• Safety Statements: 24-26-37/39

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: ((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one is an abacavir intermediate. It is used as an intermediate in the synthesis of carbocyclic sugar amines, carbanucleosides, and carbocyclic dinucleotide analogues. (1R)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one can be used as a precursor to prepare: Amino-peramivir, a potent neuraminidase inhibitor.Five membered analogs of 4-amino-5-halopentanoic acids as potential GABA aminotransferase (GABA-AT) inactivators.

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

There total 34 articles about (1R,4S)-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: 49.9%

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one (49805-30-3) → (-)-2-azabicyclo[2.2.1]hept-5-en-3-one (79200-56-9) + (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid (134003-04-6)

Guidance literature:

With (+)-γ-lactamase from Bradyrhizobium japonicum USDA 6; In aq. buffer; at 45 ℃; for 1h; pH=8; Temperature; pH-value; enantioselective reaction; Catalytic behavior; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.bmcl.2015.07.054

Reference yield:

2-azabicyclo[2.2.1.]hept-5-en-3-one (49805-30-3) → (-)-2-azabicyclo[2.2.1]hept-5-en-3-one (79200-56-9) + (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid (134003-04-6)

Guidance literature:

With lactamase; Enzymatic reaction;

DOI:10.1016/S0957-4166(01)00108-2

Reference yield:

2-azabicyclo[2.2.1.]hept-5-en-3-one (49805-30-3) → (-)-2-azabicyclo[2.2.1]hept-5-en-3-one (79200-56-9) + (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one (130931-83-8) + (1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid (134003-04-6)

Guidance literature:

With Nocardia farcinica-polyamidase (NfpolyA); In aq. phosphate buffer; at 30 ℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction;

DOI:10.1002/cctc.201402077

upstream raw materials:

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

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

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one

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

Downstream raw materials:

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

N-(2'-iodobenzyl)-2-aza-3-oxobicyclo[2.2.1]hept-5-ene

(1S,2S,4R,5R)-3-Oxa-6-aza-tricyclo[3.2.1.0^2,4]octan-7-one

(1S,2R,4S,5R)-3-oxa-6-azatricyclo[3.2.1.02,4]octan-7-one

Refernces

• 1、 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.
• 2、 Li, Wei,Wen, Huijiao,Shi, Qianqiao,Zheng, Guojun. "Study on immobilization of (+) γ-lactamase using a new type of epoxy graphene oxide carrier". . p. 270 - 276. Retrieved 2016/02/05.