methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate

Base Information

• Chemical Name: methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate
• CAS No.: 1258518-21-6
• Molecular Formula: C₁₅H₁₆O₃
• Molecular Weight: 244.29
• Mol file: 1258518-21-6.mol

Synonyms:methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate

Chemical Property of methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate

There total 4 articles about methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate 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: 45.7%

methyl 1-methacryloyl-2-phenylcyclopropane-1-carboxylate (1258517-98-4) → methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate (1258518-21-6)

Guidance literature:

With indium(III) triflate; In dichloromethane; at 25 ℃; for 30h; Inert atmosphere;

DOI:10.1021/ol102497w

Reference yield:

methyl 1-methacryloyl-2-phenylcyclopropane-1-carboxylate (1258517-98-4) + allyl-trimethyl-silane (762-72-1) → methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate (1258518-21-6) + methyl 5-allyl-4-hydroxy-5-methyl-1,2,5,6-tetrahydro-[1,1'-biphenyl]-3-carboxylate + methyl 5-allyl-4-hydroxy-5-methyl-1,2,5,6-tetrahydro-[1,1'-biphenyl]-3-carboxylate

Guidance literature:

With indium(III) triflate; In dichloromethane; at 25 ℃; for 18h; Overall yield = 38 %; Overall yield = 152.8 mg; Molecular sieve; Inert atmosphere;

DOI:10.1021/ol503305r

Reference yield:

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate (1258518-21-6)

Guidance literature:

Multi-step reaction with 3 steps

1: rhodium (II) octanoate dimer / dichloromethane / 33 h / Inert atmosphere

2: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

3: indium(III) triflate / dichloromethane / 30 h / 25 °C / Inert atmosphere

With indium(III) triflate; rhodium (II) octanoate dimer; In tetrahydrofuran; dichloromethane; 3: homo-Nazarov cyclization;

DOI:10.1021/ol102497w

upstream raw materials:

styrene

methyl 1-(methoxy(methyl)carbamoyl)-2-phenylcyclopropane-1-carboxylate

methyl 1-methacryloyl-2-phenylcyclopropane-1-carboxylate

allyl-trimethyl-silane