Silacyclobutane, 1-[[1-[(1,1-dimethylethyl)thio]ethenyl]oxy]-1-methyl- | 173343-40-3

• 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: Silacyclobutane, 1-[[1-[(1,1-dimethylethyl)thio]ethenyl]oxy]-1-methyl-
• 英文别名: 1-(1-tert-butylsulfanylethenoxy)-1-methylsiletane
• CAS: 173343-40-3
• 化学式: C₁₀H₂₀OSSi
• 分子量: 216.42
• InChiKey: ZGKGCAGMNXVCPC-UHFFFAOYSA-N

物化性质

• 沸点：
  247.3±19.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  壬醛 、 Silacyclobutane, 1-[[1-[(1,1-dimethylethyl)thio]ethenyl]oxy]-1-methyl- 在 (R)-binaphthol-titanium dichloride ((R)-BINOL-TiCl₂) 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以83%的产率得到S-tert-butyl (3S)-3-(1-methylsiletan-1-yl)oxyundecanethioate
  参考文献：
  名称：

  Highly enantioselective catalysis of the mukaiyama aldol reaction by BINOL-ti perfluorophenoxide and enoxysilacyclobutane

  摘要：

  An extremely high level of enantioselectivity is established in the Mukaiyama aldol reaction using perfluorophenol as an effective achiral ligand for binaphthol (BINOL)-derived titanium (IV) catalyst. Enoxysilacyclobutane is more effective as the silyl nucleophile than the usual trimethylsilyl enol ether in the enantioselective catalysis of the Mukaiyama aldol reaction.

  DOI：

  10.1016/0957-4166(95)00336-n

文献信息

• Asymmetric carbonyl addition reactions to benzyloxyaldehydes by binaphthol-titanium catalyst: Anti- vs. Syn-diastereofacial preference in anomalous nonchelation complexation
  作者：Koichi Mikami、Satoru Matsukawa、Eiji Sawa、Akinori Harada、Nobuaki Koga

  DOI：10.1016/s0040-4039(97)00231-1

  日期：1997.3

  An anomalous nonchelation diastereofacial selectivity is observed in the titanium-catalyzed carbonyl addition reaction to benzyl-protected alkoxyaldehydes. There is a dichotomy in the sense of syn- vs. anti-diastereofacial preference, dictated by the bulkiness of the migratory group: The sterically demanding silyl group gives syn-diastereofacial preference and the less sterically demanding proton lends to anti-diastereofacial preference. (C) 1997 Elsevier Science Ltd.