(S)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide | 155184-96-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (S)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide
• 英文别名: tert-butyl-dimethyl-[4-[(S)-methylsulfinyl]butoxy]silane
• CAS: 155184-96-6
• 化学式: C₁₁H₂₆O₂SSi
• 分子量: 250.478
• InChiKey: XDRAPABAOUDCJJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide 在 sodium azide 、 氢氟酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.5h， 生成 (S)-4-Azidobutyl methyl sulfoxide
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

  摘要：

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

  DOI：

  10.1021/jo00082a016
• 作为产物：
  描述：

  叔丁基(4-氯丁氧基)二甲基硅烷 、 (+)-(1S,2R)-trans-2-Phenylcyclohexyl (S)-methanesulfinate 在 magnesium 作用下， 生成 (S)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

  摘要：

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

  DOI：

  10.1021/jo00082a016

文献信息

• Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane
  作者：James K. Whitesell、Man-Shing Wong

  DOI：10.1021/jo00082a016

  日期：1994.2

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).