(4E)-4-[(1S,2R,3S,6R)-2-[(3S)-3-Cyclohexyl-3-hydroxyprop-1-ynyl]-3-hydroxy-7-bicyclo[4.2.0]octanylidene]butanoic acid

Base Information

• Chemical Name: (4E)-4-[(1S,2R,3S,6R)-2-[(3S)-3-Cyclohexyl-3-hydroxyprop-1-ynyl]-3-hydroxy-7-bicyclo[4.2.0]octanylidene]butanoic acid
• CAS No.: 105284-21-7
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.467
• Wikidata: Q27088639
• Pharos Ligand ID: DW452XXYPCKR
• Mol file: 105284-21-7.mol

Synonyms:RS 93427;RS 93427-007;RS-93427-007

Chemical Property of (4E)-4-[(1S,2R,3S,6R)-2-[(3S)-3-Cyclohexyl-3-hydroxyprop-1-ynyl]-3-hydroxy-7-bicyclo[4.2.0]octanylidene]butanoic acid

Chemical Property:

• Vapor Pressure: 2.17E-15mmHg at 25°C
• Boiling Point: 570.5°C at 760 mmHg
• Flash Point: 312.9°C
• Density: 1.2g/cm³
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 346.21440943
• Heavy Atom Count: 25
• Complexity: 575

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C(C#CC2C(CCC3C2CC3=CCCC(=O)O)O)O
• Isomeric SMILES: C1CCC(CC1)[C@@H](C#C[C@@H]2[C@H](CC[C@@H]\3[C@@H]2C/C3=C\CCC(=O)O)O)O

Technology Process of (4E)-4-[(1S,2R,3S,6R)-2-[(3S)-3-Cyclohexyl-3-hydroxyprop-1-ynyl]-3-hydroxy-7-bicyclo[4.2.0]octanylidene]butanoic acid

There total 14 articles about (4E)-4-[(1S,2R,3S,6R)-2-[(3S)-3-Cyclohexyl-3-hydroxyprop-1-ynyl]-3-hydroxy-7-bicyclo[4.2.0]octanylidene]butanoic 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:

1-cyclohexylprop-2-yn-1-ol (97563-45-6,105880-38-4,128241-52-1,4187-88-6) → butanoic acid, 4-[(1S,2S,3R,6S)-2-[(3S)-3-cyclohexyl-3-hydroxy-1-propynyl]-3-hydroxybicyclo[4.2.0]oct-7-ylidene]-(4Z) (105284-21-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C

2: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h

3: 71 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

4: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C

5: 40.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C

6: 55.6 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

7: 92 percent / 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C

8: 1.) dimsylsodium, sodium carbonate / 1.) 23 deg C, 20 min, 2.) 23 deg C, 4 h

With chromium(VI) oxide; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; (S)-alpine borane; sulfuric acid; boron trifluoride diethyl etherate; dimsylsodium; dihydrogen peroxide; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo00389a038

Reference yield:

cyclohexanecarbaldehyde (2043-61-0) → butanoic acid, 4-[(1S,2S,3R,6S)-2-[(3S)-3-cyclohexyl-3-hydroxy-1-propynyl]-3-hydroxybicyclo[4.2.0]oct-7-ylidene]-(4Z) (105284-21-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) ethylmagnesium bromide / 1.) THF, 2.) THF, 23 deg C, 16 h

2: 82 percent / chromium trioxide, conc. sulfuric acid / acetone / 1 h / 0 °C

3: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h

4: 71 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

5: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C

6: 40.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C

7: 55.6 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

8: 92 percent / 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C

9: 1.) dimsylsodium, sodium carbonate / 1.) 23 deg C, 20 min, 2.) 23 deg C, 4 h

With chromium(VI) oxide; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; (S)-alpine borane; sulfuric acid; boron trifluoride diethyl etherate; ethylmagnesium bromide; dimsylsodium; dihydrogen peroxide; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo00389a038

Reference yield:

1-cyclohexyl-2-propyn-1-one (7560-69-2) → butanoic acid, 4-[(1S,2S,3R,6S)-2-[(3S)-3-cyclohexyl-3-hydroxy-1-propynyl]-3-hydroxybicyclo[4.2.0]oct-7-ylidene]-(4Z) (105284-21-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) (S)-Alpine Borane, 2.) sodium hydroxide, 30 percent hydrogen peroxide / 1.) THF, 23 deg C, 16 h, 2.) THF, 40 deg C, 3 h

2: 71 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

3: 1.) n-butyllithium, 2.) boron trifluoride etherate / 1.) THF, hexane, 2.) THF, hexane, -78 deg C

4: 40.1 percent / 4-(dimethylamino)pyridine, diisopropylethylamine / 8 h / 45 °C

5: 55.6 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

6: 92 percent / 2.) 0.5 N aq. sulfuric acid / acetonitrile / 16 h / 23 °C

7: 1.) dimsylsodium, sodium carbonate / 1.) 23 deg C, 20 min, 2.) 23 deg C, 4 h

With dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; (S)-alpine borane; sulfuric acid; boron trifluoride diethyl etherate; dimsylsodium; dihydrogen peroxide; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jo00389a038

upstream raw materials:

(3-carboxypropyl)(triphenyl)phosphonium bromide

(3'S,1S,2S,3R,6S)-2-(3'-cyclohexyl-3'-hydroxyprop-1'-ynyl)-3-hydroxybicyclo<4.2.0>octan-7-one

1-cyclohexylprop-2-yn-1-ol

1-cyclohexyl-2-propyn-1-one