[(1R,2R)-Cyclohex-3-ene-1,2-diyl]dimethanol

Base Information

• Chemical Name: [(1R,2R)-Cyclohex-3-ene-1,2-diyl]dimethanol
• CAS No.: 478703-63-8
• Molecular Formula: C8H14O2
• Molecular Weight: 142.198
• DSSTox Substance ID: DTXSID20575861
• Nikkaji Number: J1.792.703E
• Mol file: 478703-63-8.mol

Synonyms:478703-63-8;[(1R,2R)-Cyclohex-3-ene-1,2-diyl]dimethanol;DTXSID20575861

Chemical Property of [(1R,2R)-Cyclohex-3-ene-1,2-diyl]dimethanol

Chemical Property:

• PSA: 40.46000
• LogP: 0.55340
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 120

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(C=C1)CO)CO
• Isomeric SMILES: C1C[C@H]([C@@H](C=C1)CO)CO

Technology Process of [(1R,2R)-Cyclohex-3-ene-1,2-diyl]dimethanol

There total 7 articles about [(1R,2R)-Cyclohex-3-ene-1,2-diyl]dimethanol 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: 71.0%

(1R,2R,3Z,5R,1'S,2'R,5'S)-5-methanesulfonyloxy-cyclohex-3-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester (479549-24-1) → ((1R,6R)-6-(hydroxymethyl)cyclohex-3-enyl)methanol (15679-28-4) + (1R,2Z,6R)-(6-hydroxymethyl-cyclohex-2-enyl)methanol (478703-63-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/1521-3773(20020802)41:15<2786::AID-ANIE2786>3.0.CO;2-Z

Reference yield:

(1R,2R,1'S,2'R,5'S)-cyclohex-4-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester (73627-88-0,109062-95-5,110416-37-0,122044-47-7) → (1R,2Z,6R)-(6-hydroxymethyl-cyclohex-2-enyl)methanol (478703-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / acetonitrile; H₂O / 12 h / 50 °C

2: 92 percent / m-CPBA; iPr₂NH / CH₂Cl₂ / 14 h / 50 °C

3: 87 percent / Et₃N / CH₂Cl₂ / -78 - -15 °C

4: 64 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(03)00816-0

Reference yield:

(1R,2R,3Z,5R,1'S,2'R,5'S)-5-hydroxy-cyclohex-3-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester (479549-21-8) → (1R,2Z,6R)-(6-hydroxymethyl-cyclohex-2-enyl)methanol (478703-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Et₃N / CH₂Cl₂ / -78 - -15 °C

2: 64 percent / LiAlH₄ / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(03)00816-0

upstream raw materials:

(1R,2R,3Z,5R,1'S,2'R,5'S)-5-methanesulfonyloxy-cyclohex-3-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester

(1R,2R,1'S,2'R,5'S)-cyclohex-4-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester

(1R,2R,3Z,5R,1'S,2'R,5'S)-5-hydroxy-cyclohex-3-ene-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester

(1R,2R,4R,5R,1'S,2'R,5'S)-4-hydroxy-5-phenylselanyl-cyclohexane-1,2-dicarboxylic acid bis(2'-isopropyl-5'-methyl-cyclohexyl) ester

Downstream raw materials:

C₄₄H₆₄N₂O₈Si₂

epi,epi-(3''S,4''S)-polycephalin C

(1Z,3R,4R,1'E)-3,4-bis(2'-iodo-vinyl)-cyclohexene

(1R,2Z,6R)-cyclohex-3-ene-1,2-dicarbaldehyde