(2-methyl-but-3-en-1-yl)-diphenyl-(phenylthiomethyl)silane

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-methyl-but-3-en-1-yl)-diphenyl-(phenylthiomethyl)silane
• 英文别名: 2-Methylbut-3-enyl-diphenyl-(phenylsulfanylmethyl)silane；2-methylbut-3-enyl-diphenyl-(phenylsulfanylmethyl)silane
• 化学式: C₂₄H₂₆SSi
• 分子量: 374.622
• InChiKey: WZCZOUSCZMIQFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  fluoro(2-methylbut-3-enyl)diphenylsilane 、 茴香硫醚 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 以80%的产率得到(2-methyl-but-3-en-1-yl)-diphenyl-(phenylthiomethyl)silane
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Silanediol Precursors from 1,5-Dihydrosiloles

  摘要：

  Dihydrosiloles are easily prepared from 1,3-dienes and dichlorosilanes, even on kilogram scale. Asymmetric hydroboration of a 3-alkyl-1,5-dihydrosilole, prepared from a 2-alkyl-1,3-diene, followed by treatment with aqueous HF results in Peterson fragmentation, forming optically active 3-alkyl-4-fluorosilyl-1-butenes. The fluorosilanes are stable to moisture but very reactive toward, nucleophiles. In addition, they can be converted to nucleophilic silyllithium reagents.

  DOI：

  10.1021/ol7021559

文献信息

• Efficient Asymmetric Synthesis of Silanediol Precursors from 1,5-Dihydrosiloles
  作者：Sushmita Sen、Madhusudhan Purushotham、Yingmei Qi、Scott McN. Sieburth

  DOI：10.1021/ol7021559

  日期：2007.11.1

  Dihydrosiloles are easily prepared from 1,3-dienes and dichlorosilanes, even on kilogram scale. Asymmetric hydroboration of a 3-alkyl-1,5-dihydrosilole, prepared from a 2-alkyl-1,3-diene, followed by treatment with aqueous HF results in Peterson fragmentation, forming optically active 3-alkyl-4-fluorosilyl-1-butenes. The fluorosilanes are stable to moisture but very reactive toward, nucleophiles. In addition, they can be converted to nucleophilic silyllithium reagents.