1,1-diphenyl 4-acetoxy 1-silacyclopentan-3-ol | 1450667-22-7

• 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: 1,1-diphenyl 4-acetoxy 1-silacyclopentan-3-ol
• 英文别名: (3R,4R)-4-hydroxy-1,1-diphenylsilolan-3-yl acetate
• CAS: 1450667-22-7
• 化学式: C₁₈H₂₀O₃Si
• 分子量: 312.44
• InChiKey: VYRUVFJAADQLRL-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,1-diphenyl 4-acetoxy 1-silacyclopentan-3-ol 在 叔丁基过氧化氢 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以52%的产率得到(R)-3-丁烯-1,2-二醇
  参考文献：
  名称：

  Preparation of enantioenriched tetraols and triolamines from a common epoxide

  摘要：

  We identify a silylcyclopentene oxide that is amenable to several distinct asymmetric catalytic transformations providing access to enantio-enriched tetraol and triol-amines. The sequence employed allows for selective protection of one amine or alcohol from the four heteroatoms that are introduced into the carbon scaffold. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.001
• 作为产物：
  描述：

  (3S,4R)-4-chloro-1,1-diphenylsilolan-3-ol 在 (R,R)-Jacobsen catalyst 、 C₃₆H₅₂ClCoN₂O₂^(1-) 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 1,1-diphenyl 4-acetoxy 1-silacyclopentan-3-ol 、 [(3S,4S)-4-hydroxy-1,1-diphenylsilolan-3-yl] acetate
  参考文献：
  名称：

  Preparation of enantioenriched tetraols and triolamines from a common epoxide

  摘要：

  We identify a silylcyclopentene oxide that is amenable to several distinct asymmetric catalytic transformations providing access to enantio-enriched tetraol and triol-amines. The sequence employed allows for selective protection of one amine or alcohol from the four heteroatoms that are introduced into the carbon scaffold. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.001

文献信息

• Sila et germacyclopentanes C-bifonctionnels
  作者：Georges Manuel、Rabah Boukherroub

  DOI：10.1016/0022-328x(93)80235-4

  日期：1993.4

  C-bifunctional sila- and germacyclopentanes have some potential as biologically active drugs. Ten representative 1-sila (and 1-germa) cyclopentane-2,3 and 3,4-diols, cis or trans, were synthesized from the corresponding 1-metallacyclopen-3-enes. The influence of the metal, silicon or germanium, on each step leading to 3 sets of alpha-diols is underlined. The stereochemistry of the alpha-diols and their precursors was established by H-1 and C-13 NMR spectroscopy.