7-cyclohexyl-7-methyl-5,9-dihydro-6,8-dioxa-7-sila-benzocycloheptene | 1086090-69-8

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 7-cyclohexyl-7-methyl-5,9-dihydro-6,8-dioxa-7-sila-benzocycloheptene
• 英文别名: 3-Cyclohexyl-3-methyl-1,5-dihydro-2,4,3-benzodioxasilepine
• CAS: 1086090-69-8
• 化学式: C₁₅H₂₂O₂Si
• 分子量: 262.424
• InChiKey: IVKVFNSUXBPRIE-UHFFFAOYSA-N

物化性质

• 沸点：
  346.4±31.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-cyclohexyl-7-methyl-5,9-dihydro-6,8-dioxa-7-sila-benzocycloheptene 、 叔丁基锂 在 (4S,4′S)-(-)-2,2′-(3-戊烯基)双(4-异丙基噁唑啉) 作用下， 以 正己烷 为溶剂， 生成 (S)-[2-(tert-butyl-cyclohexyl-methyl-silanyloxymethyl)phenyl]methanol 、 (R)-[2-(tert-butyl-cyclohexyl-methyl-silanyloxymethyl)phenyl]methanol
  参考文献：
  名称：

  Enantioselective Synthesis of Silanol

  摘要：

  An enantioselective nucleophilic substitution reaction of achiral dialkoxysilane has been developed. The reaction proceeds with efficient stereocontrol on the silicon chirality center to give the enantioenriched silyl ether, which can be converted to the silanol without loss of enantiopurity. We have analyzed the steric course of the reaction by using DFT calculations and propose a transition state model to explain the observed enantioselectivity.

  DOI：

  10.1021/ja805848z
• 作为产物：
  描述：

  甲基二氯环己基硅烷 、 邻苯二甲醇 在 咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以18%的产率得到7-cyclohexyl-7-methyl-5,9-dihydro-6,8-dioxa-7-sila-benzocycloheptene
  参考文献：
  名称：

  Enantioselective Synthesis of Silanol

  摘要：

  An enantioselective nucleophilic substitution reaction of achiral dialkoxysilane has been developed. The reaction proceeds with efficient stereocontrol on the silicon chirality center to give the enantioenriched silyl ether, which can be converted to the silanol without loss of enantiopurity. We have analyzed the steric course of the reaction by using DFT calculations and propose a transition state model to explain the observed enantioselectivity.

  DOI：

  10.1021/ja805848z

文献信息

• Enantioselective Synthesis of Silanol
  作者：Kazunobu Igawa、Junko Takada、Tomohiro Shimono、Katsuhiko Tomooka

  DOI：10.1021/ja805848z

  日期：2008.12.3

  An enantioselective nucleophilic substitution reaction of achiral dialkoxysilane has been developed. The reaction proceeds with efficient stereocontrol on the silicon chirality center to give the enantioenriched silyl ether, which can be converted to the silanol without loss of enantiopurity. We have analyzed the steric course of the reaction by using DFT calculations and propose a transition state model to explain the observed enantioselectivity.