(1S,2R,5S,6S,7R)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

Base Information

• Chemical Name: (1S,2R,5S,6S,7R)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one
• CAS No.: 139405-39-3
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.43

Synonyms:(1S,2R,5S,6S,7R)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

Chemical Property of (1S,2R,5S,6S,7R)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

Chemical Property:

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Technology Process of (1S,2R,5S,6S,7R)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

There total 3 articles about (1S,2R,5S,6S,7R)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one 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:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2R,5S,6S,7R)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one (139405-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / CH₂Cl₂ / 15 h / Ambient temperature

2: p-toluenesulfonic acid / benzene / 3 h / Heating

With toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1021/ja00262a006

Reference yield:

(1S,2R,5S)-(+)-menthol (15356-60-2) + (3R*,3aR*,4S*,7R*,7aS*)-3-hydroxy-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one (56232-16-7,72937-64-5,72937-66-7,72937-71-4,117142-76-4,117469-15-5) → (1S,2R,5S,6S,7R)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one (139405-39-3) + (1R,2S,5R,6R,7S)-5-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one (72902-82-0)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 3h; Yield given. Yields of byproduct given; Heating;

DOI:10.1021/ja00262a006

Reference yield:

5-(1)-menthyloxy-2(5H)-furanone (370874-78-5) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → <3R-<3α(1R,2S,5R),3aα,4α,7α,7aα>>-3a,4,7,7a-tetrahydro-3-<<5-methyl-2-(1-methyl-ethyl)-cyclohexyl>oxy>-4,7-methanoisobenzofuran-1(3H)-one (72937-74-7) + (1R,2S,5S,6R,7S)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.02,6]dec-8-en-3-one (72902-82-0,72937-74-7,99685-54-8,139405-39-3)

Guidance literature:

In toluene; at 110 ℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00240a048

upstream raw materials:

5-⁽¹⁾-menthyloxy-2(5H)-furanone

cyclopenta-1,3-diene

(1S,2R,5S)-(+)-menthol

(3R*,3aR*,4S*,7R*,7aS*)-3-hydroxy-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one

Downstream raw materials:

(2S,5R,6R)-5-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-2-methyl-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

(1S,2R,3S,4R)-3-Vinyl-bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

(2S,6R)-4-Oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

(2S,5R,6R)-2-Ethyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one

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