methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate
• CAS No.: 115162-78-2
• Molecular Formula: C₁₄H₁₆O₃Se
• Molecular Weight: 311.239
• Mol file: 115162-78-2.mol

Synonyms:methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate

Chemical Property of methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate

There total 4 articles about methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate 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: 73.0%

diphenyl diselenide (1666-13-3) + 7-Oxabicyclo<4.1.0>hept-4-en-4-carbonsaeure-methylester (77611-97-3) → methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate (115162-78-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 4h;

DOI:10.1021/jo00249a022

Reference yield:

methyl cyclohexa-1,3-diene-1-carboxylate (30810-15-2) → methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate (115162-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / m-CPBA / CH₂Cl₂ / 1.) -70 deg C, 30 min, 2.) RT, 2 h

2: 73 percent / NaBH₄ / methanol / 4 h / 0 °C

With sodium tetrahydroborate; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1021/jo00249a022

Reference yield:

2-Diethylamino-cyclohex-3-enecarboxylic acid methyl ester (201275-17-4) → methyl 3β-(phenylseleno)4α-hydroxycyclohex-1-ene-1-carboxylate (115162-78-2)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / 21 h / Ambient temperature

2: DBU / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 99 percent / m-CPBA / CH₂Cl₂ / 1.) -70 deg C, 30 min, 2.) RT, 2 h

4: 73 percent / NaBH₄ / methanol / 4 h / 0 °C

With sodium tetrahydroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1021/jo00249a022

upstream raw materials:

diphenyl diselenide

7-Oxabicyclo<4.1.0>hept-4-en-4-carbonsaeure-methylester

methyl cyclohexa-1,3-diene-1-carboxylate

2-Diethylamino-cyclohex-3-enecarboxylic acid methyl ester

Downstream raw materials:

methyl 1β,4α-dihydroxycyclohex-2-ene-1-carboxylate

1β-<1-(carboxyethenyl)oxy>-4α-hydroxycyclohex-2-ene-1-carboxylic acid

methyl 1β-<<1-(methoxycarbonyl)ethenyl>oxy>-4α-hydroxycyclohex-2-ene-1-carboxylate

(1R,4R)-1,4-Diacetoxy-cyclohex-2-enecarboxylic acid methyl ester