(1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

Base Information

Chemical Name:(1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene
CAS No.:1309435-01-5
Molecular Formula:C₂₁H₂₂O₂S
Molecular Weight:338.47
Hs Code.:

Synonyms:(1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

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Chemical Property of (1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

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Technology Process of (1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

There total 4 articles about (1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene 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: 35.0%

: 7-bromo-2-(4-methoxyphenyl)bicyclo[2.2.1]hept-2-ene

: 1517-82-4
(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

: 1309435-01-5
(1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

: 1309435-02-6
(1S,4R,7S)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

Guidance literature:: 7-bromo-2-(4-methoxyphenyl)bicyclo[2.2.1]hept-2-ene; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 2h; Inert atmosphere;

With magnesium chloride; In tetrahydrofuran; pentane; at -78 ℃; for 0.5h; Inert atmosphere;

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate; In tetrahydrofuran; pentane; at -78 ℃; for 4h; optical yield given as %ee; Inert atmosphere; Resolution of racemate;
DOI:10.1021/ol200841x

Reference yield:

: 498-66-8
norborn-2-ene

: 1309435-01-5
(1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

: 1309435-02-6
(1S,4R,7S)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: N-Bromosuccinimide / water / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: lanthanum trichloride lithium chloride complex / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.2: 4 h / -78 - 20 °C / Inert atmosphere

3.3: -78 °C / Inert atmosphere

4.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 °C / Inert atmosphere

4.3: 4 h / -78 °C / Inert atmosphere; Resolution of racemate

With N-Bromosuccinimide; oxalyl dichloride; lanthanum trichloride lithium chloride complex; tert.-butyl lithium; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water; pentane; 2.1: Swern oxidation;
DOI:10.1021/ol200841x

Reference yield:

: 20047-65-8
syn-7-bromonorbornene

: 1309435-01-5
(1R,4S,7R)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

: 1309435-02-6
(1S,4R,7S)-2-(4-methoxyphenyl)-7-((R)-p-tolylsulfinyl)-bicyclo[2.2.1]hept-2-ene

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: lanthanum trichloride lithium chloride complex / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.2: 4 h / -78 - 20 °C / Inert atmosphere

2.3: -78 °C / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

3.3: 4 h / -78 °C / Inert atmosphere; Resolution of racemate

With oxalyl dichloride; lanthanum trichloride lithium chloride complex; tert.-butyl lithium; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; pentane; 1.1: Swern oxidation;
DOI:10.1021/ol200841x