(1R,6S)-6-Carbamoyl-3-cyclohexene-1-carboxylic acid

Base Information

• Chemical Name: (1R,6S)-6-Carbamoyl-3-cyclohexene-1-carboxylic acid
• CAS No.: 1469-49-4
• Molecular Formula: C₈H₁₁NO₃
• Molecular Weight: 169.18
• DSSTox Substance ID: DTXSID301339277,DTXSID201339505
• Nikkaji Number: J952.022H
• Mol file: 1469-49-4.mol

Synonyms:1469-49-4;SCHEMBL7546289;DTXSID201339505;DTXSID301339277;207518-95-4;(1R,6S)-6-Carbamoyl-3-cyclohexene-1-carboxylic acid;Rel-(1R,6S)-6-carbamoylcyclohex-3-ene-1-carboxylic acid;(1R,6S)-6-(Aminocarbonyl)-3-cyclohexene-1-carboxylic acid

Chemical Property of (1R,6S)-6-Carbamoyl-3-cyclohexene-1-carboxylic acid

Chemical Property:

• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 169.07389321
• Heavy Atom Count: 12
• Complexity: 235

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CCC(C1C(=O)N)C(=O)O
• Isomeric SMILES: C1C=CC[C@H]([C@H]1C(=O)N)C(=O)O

Technology Process of (1R,6S)-6-Carbamoyl-3-cyclohexene-1-carboxylic acid

There total 6 articles about (1R,6S)-6-Carbamoyl-3-cyclohexene-1-carboxylic 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: 100.0%

cis-1,2,3,6-tetrahydrophthalic anhydride (935-79-5) → 6-carbamoylcyclohex-3-enecarboxylic acid (1469-49-4,2028-12-8)

Guidance literature:

With ammonium hydroxide; at 25 ℃;

DOI:10.1021/jm990965x

Reference yield: 85.0%

(1S,2R)-Cyclohex-4-ene-1,2-dicarboxylic acid diamide (28907-18-8) → cis-1,2,3,6-tetrahydrophthalamic acid (1469-49-4,2028-12-8)

Guidance literature:

With amidase from Rhodococcus erythropolis AJ₂₇₀ (variant I₄₅₀A/F₁₄₆A/W₃₂₈F) containing E_. coli BL₂₁ (DE₃) PlysS whole cells; In aq. phosphate buffer; at 37 ℃; for 8h; pH=7; Enzymatic reaction;

DOI:10.1002/adsc.202100597

Reference yield: 33.0%

(1R,2S)-Cyclohex-4-ene-1,2-dicarbonitrile (28907-19-9) → cis-1,2,3,6-tetrahydrophthalic acid (2305-26-2) + cis-1,2,3,6-tetrahydrophthalamic acid (1469-49-4,2028-12-8) + (1R,6S)-6-Carbamoyl-cyclohex-3-enecarboxylic acid

Guidance literature:

With Rhodococcus rhodochrous IFO 15564; water; Yields of byproduct given;

DOI:10.1016/S0957-4166(98)00084-6

upstream raw materials:

(1R,2S)-Cyclohex-4-ene-1,2-dicarbonitrile

cis-1,2,3,6-Tetrahydrophthalimide

(1S,2R)-Cyclohex-4-ene-1,2-dicarboxylic acid diamide

cis-1,2,3,6-tetrahydrophthalic anhydride

Downstream raw materials:

trans-2-amino-4-cyclohexene-1-carboxylic acid

((1S,6S)-6-Hydroxymethyl-cyclohex-3-enyl)-carbamic acid ethyl ester

trans-2-(p-clorophenyl)-1,2,4a,5,8,8a-hexahydro-4H-3,1-benzoxazine

trans-2-(hydroxymethyl)-4-cyclohexenyl-1-amine