14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,2,7,12,14-pentaene

Base Information

• Chemical Name: 14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,2,7,12,14-pentaene
• CAS No.: 1644030-69-2
• Molecular Formula: C₂₇H₂₇ClO₆S
• Molecular Weight: 515.027
• Mol file: 1644030-69-2.mol

Synonyms:

Chemical Property of 14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,2,7,12,14-pentaene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,2,7,12,14-pentaene

There total 4 articles about 14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.0^3,8]pentadeca-1⁽¹¹⁾,2,7,12,14-pentaene 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: 71.0%

dimethyl 2-[5-(4-chlorophenyl)-5-methyl-2-phenylsulfonylhexa-2,3-dienyl]-2-(prop-2-ynyl)malonate (1644030-59-0) → 14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.03,8]pentadeca-1(11),2,7,12,14-pentaene (1644030-69-2)

Guidance literature:

With di(rhodium)tetracarbonyl dichloride; In toluene; for 0.5h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201403990

Reference yield:

dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate (1644031-10-6) → 14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.03,8]pentadeca-1(11),2,7,12,14-pentaene (1644030-69-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3: di(rhodium)tetracarbonyl dichloride / toluene / 0.5 h / Inert atmosphere; Reflux

With di(rhodium)tetracarbonyl dichloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/anie.201403990

Reference yield:

α,α-dimethyl-(4-chlorophenyl)acetaldehyde (20401-29-0) → 14-chloro-5,5-bis(methoxycarbonyl)-10,10-dimethyl-7-phenylsulfonyltricyclo[9.4.0.03,8]pentadeca-1(11),2,7,12,14-pentaene (1644030-69-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.08 h / -78 °C / Inert atmosphere

2.1: triethylamine / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: di(rhodium)tetracarbonyl dichloride / toluene / 0.5 h / Inert atmosphere; Reflux

With di(rhodium)tetracarbonyl dichloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/anie.201403990

upstream raw materials:

α,α-dimethyl-(4-chlorophenyl)acetaldehyde

dimethyl 2-[5-(4-chlorophenyl)-4-hydroxy-5-methylhex-2-ynyl]-2-(prop-2-ynyl)malonate

dimethyl 2-[5-(4-chlorophenyl)-5-methyl-2-phenylsulfonylhexa-2,3-dienyl]-2-(prop-2-ynyl)malonate

dimethyl 2,2-di(prop-2-ynyl)malonate