(1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile

Base Information

• Chemical Name: (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile
• CAS No.: 24425-58-9
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.176
• DSSTox Substance ID: DTXSID801180465
• Nikkaji Number: J953.769D

Synonyms:24425-58-9;SCHEMBL13409251;DTXSID801180465;rel-(1R,2S,3R,4S)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile

Chemical Property of (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 144.068748264
• Heavy Atom Count: 11
• Complexity: 268

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C(C2C#N)C#N
• Isomeric SMILES: C1[C@@H]2C=C[C@H]1[C@H]([C@H]2C#N)C#N

Technology Process of (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile

There total 6 articles about (1S,2R,3S,4R)-bicyclo[2.2.1]hept-5-ene-2,3-dicarbonitrile 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: 100.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + 1,2-Dicyanoethylene (764-42-1) → bicyclo<2.2.1>hept-5,6-ene-2α,3β-dicarbonitrile (6343-16-4,24425-58-9,38447-89-1,51252-31-4)

Guidance literature:

In methanol; at 0 - 20 ℃;

DOI:10.1080/00304940209355789

Reference yield:

3-oxatetracyclo<3,3,0,02,804,6>octane (175879-37-5) + 1,2-Dicyanoethylene (764-42-1) → bicyclo<2.2.1>hept-5,6-ene-2α,3β-dicarbonitrile (6343-16-4,24425-58-9,38447-89-1,51252-31-4) + (1R,2S,5R,6S,7S,8S)-9-Oxa-tricyclo[4.2.1.12,5]dec-3-ene-7,8-dicarbonitrile

Guidance literature:

at 150 - 200 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/0040-4039(96)00062-7

Reference yield:

maleonitrile (928-53-0,764-42-1,17656-09-6,62600-65-1,62742-11-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → norbornene-(5)-dicarbonitrile-(2endo.3endo) (24425-58-9) + 5,6-Dicyan-bicyclo[2.2.1]hepten-(2) (38447-89-1)

Guidance literature:

In 1,4-dioxane;

upstream raw materials:

maleonitrile

cyclopenta-1,3-diene

1,2-Dicyanoethylene

3-oxatetracyclo<3,3,0,0^2,80^4,6>octane

Downstream raw materials:

(+/-)-norbornane-dicarbonitrile-(2endo.3exo)

anti-1,2,3,4,5,6,7,8-octahydro-1,4,5,8-dimethano-naphthalene anti-sesquinorbornene

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