[(3Z,6S,7E)-trideca-3,7-dien-9,12-diyn-6-yl] benzoate

Base Information

• Chemical Name: [(3Z,6S,7E)-trideca-3,7-dien-9,12-diyn-6-yl] benzoate
• CAS No.: 853929-60-9
• Molecular Formula: C₂₀H₂₀O₂
• Molecular Weight: 292.378
• DSSTox Substance ID: DTXSID701202626
• Nikkaji Number: J2.170.810K
• Mol file: 853929-60-9.mol

Synonyms:DTXSID701202626;853929-60-9;3,7-Tridecadiene-9,12-diyn-6-ol, 6-benzoate, (3Z,6S,7E)-

Chemical Property of [(3Z,6S,7E)-trideca-3,7-dien-9,12-diyn-6-yl] benzoate

Chemical Property:

• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 292.146329876
• Heavy Atom Count: 22
• Complexity: 498

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC=CCC(C=CC#CCC#C)OC(=O)C1=CC=CC=C1
• Isomeric SMILES: CC/C=C\C[C@@H](/C=C/C#CCC#C)OC(=O)C1=CC=CC=C1

Technology Process of [(3Z,6S,7E)-trideca-3,7-dien-9,12-diyn-6-yl] benzoate

There total 7 articles about [(3Z,6S,7E)-trideca-3,7-dien-9,12-diyn-6-yl] benzoate 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:

(S)-1-Benzyloxy-hept-4-yn-2-ol (853929-46-1) → Benzoic acid (E)-(S)-((Z)-1-pent-2-enyl)-oct-2-ene-4,7-diynyl ester (853929-60-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 94 percent / pyridine / 0 - 20 °C

2.1: 96 percent / H₂ / Lindlar cat. / hexane

3.1: 85 percent / EtSH; AlCl₃ / CH₂Cl₂ / -35 °C

4.1: 84 percent / Py*SO₃; DMSO; Et₃N / CH₂Cl₂ / 20 °C

5.1: CrCl₂ / tetrahydrofuran / 20 °C

6.1: 50 percent / n-PrNH₂; CuI / Pd(Ph₃)4 / benzene / 20 °C

7.1: AgNO₃ / methanol; H₂O

7.2: NaCN

With pyridine; chromium dichloride; propylamine; copper(l) iodide; aluminium trichloride; hydrogen; sulfur trioxide pyridine complex; silver nitrate; dimethyl sulfoxide; triethylamine; ethanethiol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Lindlar catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; benzene; 4.1: Swern oxidation / 5.1: Takai olefination;

DOI:10.1016/j.tetlet.2005.03.175

Reference yield:

Benzoic acid (Z)-(S)-1-((E)-2-iodo-vinyl)-hex-3-enyl ester → Benzoic acid (E)-(S)-((Z)-1-pent-2-enyl)-oct-2-ene-4,7-diynyl ester (853929-60-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 50 percent / n-PrNH₂; CuI / Pd(Ph₃)4 / benzene / 20 °C

2.1: AgNO₃ / methanol; H₂O

2.2: NaCN

With propylamine; copper(l) iodide; silver nitrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; water; benzene;

DOI:10.1016/j.tetlet.2005.03.175

Reference yield:

Benzoic acid (Z)-(S)-1-hydroxymethyl-hex-3-enyl ester (853929-51-8) → Benzoic acid (E)-(S)-((Z)-1-pent-2-enyl)-oct-2-ene-4,7-diynyl ester (853929-60-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 84 percent / Py*SO₃; DMSO; Et₃N / CH₂Cl₂ / 20 °C

2.1: CrCl₂ / tetrahydrofuran / 20 °C

3.1: 50 percent / n-PrNH₂; CuI / Pd(Ph₃)4 / benzene / 20 °C

4.1: AgNO₃ / methanol; H₂O

4.2: NaCN

With chromium dichloride; propylamine; copper(l) iodide; sulfur trioxide pyridine complex; silver nitrate; dimethyl sulfoxide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; benzene; 1.1: Swern oxidation / 2.1: Takai olefination;

DOI:10.1016/j.tetlet.2005.03.175

upstream raw materials:

Benzoic acid (E)-(S)-1-((Z)-pent-2-enyl)-8-trimethylsilanyl-oct-2-ene-4,7-diynyl ester

(S)-1-Benzyloxy-hept-4-yn-2-ol

Benzoic acid (Z)-(S)-1-hydroxymethyl-hex-3-enyl ester

Benzoic acid (Z)-(S)-1-benzyloxymethyl-hex-3-enyl ester

Downstream raw materials:

C₃₇H₄₂O₆

7(S),17(S)-resolvin D5

C₃₇H₃₈O₆