(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:

97% ^*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
• General Description: (1S,4R)-2-Azabicyclo[2.2.1]hept-5-en-3-one, also known as Vince lactam, is a chiral bicyclic γ-lactam widely used as a key intermediate in the synthesis of carbocyclic nucleosides and other pharmaceuticals. It can be enantioselectively resolved through methods such as inclusion complexation with brucine, lipase-catalyzed transesterification, or enzymatic resolution using γ-lactamases, which exhibit high substrate tolerance and enantioselectivity. (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one serves as a versatile scaffold for constructing rigid bicycloheterocyclic structures, making it valuable in medicinal chemistry and combinatorial synthesis.

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-aminocyclopenten-2-ene-1-carboxylic acid

(1S)-2-(allyl)-2-azabicyclo[2.2.1]hept-5-en-3-one

(-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate]

C₇H₁₃NO₂