(1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Base Information

• Chemical Name: (1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester
• CAS No.: 258522-20-2
• Molecular Formula: C₂₈H₃₀O₂
• Molecular Weight: 398.545

Synonyms:(1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

Chemical Property of (1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

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Technology Process of (1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

There total 3 articles about (1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester 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: 70.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (1R,9R)-11-Methylene-13-oxo-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (258522-19-9) → (1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (258522-20-2)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; at 20 ℃; for 0.5h;

(1R,9R)-11-Methylene-13-oxo-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1016/S0040-4039(99)01874-2

Reference yield:

(1R,2S)-trans-2-phenylcyclohexanol (98919-68-7) → (1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (258522-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 94 percent / benzene / 30 h / Heating

2.1: 70 percent / Pd(PPh₃)4; 1,1,3,3-tetramethyl guanidine / dioxane / 14 h / 20 °C

3.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C

3.2: 70 percent / tetrahydrofuran / 1.5 h / 0 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; benzene; 1.1: Esterification / 2.1: bicycloannulation / 3.1: deprotonation / 3.2: Wittig reaction;

DOI:10.1016/S0040-4039(99)01874-2

Reference yield:

2-Oxo-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (258522-18-8) → (1S,9R)-11,13-Dimethylene-tricyclo[7.3.1.02,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester (258522-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 70 percent / Pd(PPh₃)4; 1,1,3,3-tetramethyl guanidine / dioxane / 14 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / 0.5 h / 20 °C

2.2: 70 percent / tetrahydrofuran / 1.5 h / 0 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 1,4-dioxane; 1.1: bicycloannulation / 2.1: deprotonation / 2.2: Wittig reaction;

DOI:10.1016/S0040-4039(99)01874-2

upstream raw materials:

Methyltriphenylphosphonium bromide

(1R,9R)-11-Methylene-13-oxo-tricyclo[7.3.1.0^2,7]trideca-2,4,6-triene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

(1R,2S)-trans-2-phenylcyclohexanol

2-Oxo-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid (1R,2S)-2-phenyl-cyclohexyl ester

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