(1S*,3R*)-1-Cyclohexyl-3-(dimethylphenylsilyl)butanol

• 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: (1S*,3R*)-1-Cyclohexyl-3-(dimethylphenylsilyl)butanol
• 英文别名: (1S,3R)-1-cyclohexyl-3-[dimethyl(phenyl)silyl]butan-1-ol
• 化学式: C₁₈H₃₀OSi
• 分子量: 290.521
• InChiKey: YMDJJHIONUBUMX-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-Cyclohexyl-3-(dimethylphenylsilyl)prop-2-ynol tert-butyldimethylsilyl ether 在 Rh(norbornadiene)(bis(diphenylphosphino)butane)(+)BF4(-) 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1S*,3R*)-1-Cyclohexyl-3-(dimethylphenylsilyl)butanol
  参考文献：
  名称：

  Exploring the reactivity of alkenes bearing silicon and/or tin in the hydroxyl-directed hydrogenation. A diastereoselective synthesis of heterobimetallic compounds

  摘要：

  The hydroxyl-directed hydrogenation of (E)- and (Z)-gamma-hydroxy vinylstannanes and silanes has been studied in the presence of (dppb)Rh(NBD)BF4 (1). Efficient routes to gamma-hydroxy stannanes and silanes have been developed. Diastereoselectivities from 60 to >500:1 were observed. A significant difference in reaction rate and pathway was observed between the (E)- and (Z)-vinylstannanes. We observed a reductive destannation process for the (Z)-stannanes which was influenced by the size of the R group. Competition studies were carried out to determine if steric or electronic effects were responsible for the reactivity patterns observed.

  DOI：

  10.1021/jo00100a023

文献信息

• Lautens, Mark; Zhang, ChunHao; Crudden, Cathleen M., Angewandte Chemie, 1992, vol. 104, # 2, p. 237 - 239
  作者：Lautens, Mark、Zhang, ChunHao、Crudden, Cathleen M.

  DOI：——

  日期：——
• Exploring the reactivity of alkenes bearing silicon and/or tin in the hydroxyl-directed hydrogenation. A diastereoselective synthesis of heterobimetallic compounds
  作者：Mark Lautens、C. H. Zhang、Betty Jane Goh、Cathleen M. Crudden、Marc J. A. Johnson

  DOI：10.1021/jo00100a023

  日期：1994.10

  The hydroxyl-directed hydrogenation of (E)- and (Z)-gamma-hydroxy vinylstannanes and silanes has been studied in the presence of (dppb)Rh(NBD)BF4 (1). Efficient routes to gamma-hydroxy stannanes and silanes have been developed. Diastereoselectivities from 60 to >500:1 were observed. A significant difference in reaction rate and pathway was observed between the (E)- and (Z)-vinylstannanes. We observed a reductive destannation process for the (Z)-stannanes which was influenced by the size of the R group. Competition studies were carried out to determine if steric or electronic effects were responsible for the reactivity patterns observed.