ethyl (Z)-4-carboxymethylene-ε-caprolactone

Base Information

• Chemical Name: ethyl (Z)-4-carboxymethylene-ε-caprolactone
• CAS No.: 1422253-49-3
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• Mol file: 1422253-49-3.mol

Synonyms:

Chemical Property of ethyl (Z)-4-carboxymethylene-ε-caprolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (Z)-4-carboxymethylene-ε-caprolactone

There total 3 articles about ethyl (Z)-4-carboxymethylene-ε-caprolactone 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: 61.0%

(4-oxocyclohexylidene)acetic acid ethyl ester (159454-98-5) → ethyl 2-(4-hydroxycyclohexylidene)acetate (16700-13-3) + ethyl (Z)-4-carboxymethylene-ε-caprolactone (1422253-49-3)

Guidance literature:

With cyclohexanone monooxygenase Phe₄₃₂Ile/Thr₄₃₃Gly/Leu₁₄₃Met/Phe₅₀₅Cys; for 12h; diastereoselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.201200759

Reference yield:

cyclohexanedione monoethylene ketal (4746-97-8) → ethyl 2-(4-hydroxycyclohexylidene)acetate (16700-13-3) + ethyl (Z)-4-carboxymethylene-ε-caprolactone (1422253-49-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -70 °C

1.2: -70 - 20 °C

2.1: hydrogenchloride / tetrahydrofuran; water / 19 h

3.1: triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / 70 °C

4.1: cyclohexanone monooxygenase Phe₄₃₂Ile/Thr₄₃₃Gly/Leu₁₄₃Met/Phe₅₀₅Cys / 12 h / Enzymatic reaction

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cyclohexanone monooxygenase Phe₄₃₂Ile/Thr₄₃₃Gly/Leu₁₄₃Met/Phe₅₀₅Cys; sodium hexamethyldisilazane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; water; 4.1: |Baeyer-Villiger Ketone Oxidation;

DOI:10.1002/adsc.201200759

Reference yield:

8-(bromomethylene)-1,4-dioxaspiro[4.5]decane (923584-02-5) → ethyl 2-(4-hydroxycyclohexylidene)acetate (16700-13-3) + ethyl (Z)-4-carboxymethylene-ε-caprolactone (1422253-49-3)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / tetrahydrofuran; water / 19 h

2: triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / 70 °C

3: cyclohexanone monooxygenase Phe₄₃₂Ile/Thr₄₃₃Gly/Leu₁₄₃Met/Phe₅₀₅Cys / 12 h / Enzymatic reaction

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cyclohexanone monooxygenase Phe₄₃₂Ile/Thr₄₃₃Gly/Leu₁₄₃Met/Phe₅₀₅Cys; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; water; 3: |Baeyer-Villiger Ketone Oxidation;

DOI:10.1002/adsc.201200759

upstream raw materials:

(4-oxocyclohexylidene)acetic acid ethyl ester

cyclohexanedione monoethylene ketal

8-(bromomethylene)-1,4-dioxaspiro[4.5]decane