tert-butyl(dimethyl)[(2-methylenecyclohexyl)oxy]silane | 72726-56-8

• 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: tert-butyl(dimethyl)[(2-methylenecyclohexyl)oxy]silane
• 英文别名: 2-(tert-butyldimethylsilanyloxy)cyclohexylmethylene；2-methylene-1-(tert-butyldimethylsiloxy)cyclohexane；2-methylenecyclohexyl tert-butyldimethylsilyl ether；tert-Butyl(dimethyl)[(2-methylidenecyclohexyl)oxy]silane；tert-butyl-dimethyl-(2-methylidenecyclohexyl)oxysilane
• CAS: 72726-56-8
• 化学式: C₁₃H₂₆OSi
• 分子量: 226.434
• InChiKey: MGDYSUMJFNUCHO-UHFFFAOYSA-N

物化性质

• 沸点：
  241.6±29.0 °C(Predicted)
• 密度：
  0.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  tert-butyl(dimethyl)[(2-methylenecyclohexyl)oxy]silane 生成 [(1R,2R)-2-[tert-butyl(dimethyl)silyl]oxycyclohexyl]methanol
  参考文献：
  名称：

  EVANS, DAVID A.;FU, GREGORY C.;HOVEYDA, ARMIR H., J. AMER. CHEM. SOC., 110,(1988) N 20, C. 6917-6918

  摘要：

  DOI：
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 碘 、 sodium 作用下， 以 乙腈 为溶剂， 反应 20.08h， 生成 tert-butyl(dimethyl)[(2-methylenecyclohexyl)oxy]silane
  参考文献：
  名称：

  Silyl halides from (phenylseleno)silanes. Reaction with oxiranes and alcohols to give hydrolytically stable silyl ethers

  摘要：

  DOI：

  10.1021/jo00320a012

文献信息

• Highly Efficient Synthesis of Terminal Alkenes from Ketones
  作者：Hélène Lebel、Danielle Guay、Valérie Paquet、Kim Huard

  DOI：10.1021/ol049085p

  日期：2004.9.1

  [reaction: see text] The rhodium(I)-catalyzed methylenation of ketones using trimethylsilyldiazomethane proceeds to give the corresponding alkenes in good yields (60-97%). The use of an excess of 2-propanol and 1,4-dioxane as a solvent were instrumental to obtain the desired alkenes in high yields. Superior results were achieved with the rhodium(I)-catalyzed methylenation in comparison with the standard

  [反应：见正文]使用三甲基甲硅烷基重氮甲烷进行铑（I）催化的酮的甲基化反应，得到了相应的烯烃，收率很高（60-97％）。使用过量的2-丙醇和1，4-二恶烷作为溶剂有助于以高收率获得所需的烯烃。与标准Wittig反应相比，铑（I）催化的亚甲基化获得了优异的结果。
• Substrate-Controlled Highly Diastereoselective Synthesis of Primary and Secondary Diorganozinc Reagents by a Hydroboration/Boron–Zinc Exchange Sequence
  作者：Eike Hupe、M. Isabel Calaza、Paul Knochel

  DOI：10.1002/chem.200204662

  日期：2003.6.16

  The scope of substrate-controlled diastereoselective hydroborations can be considerably enhanced by a boron-zinc exchange reaction, providing organozinc derivatives that react with a broad range of electrophiles. Even normally unreactive boronic esters, obtained by Rh-catalyzed hydroboration with catecholborane, react readily with iPr2Zn providing the corresponding zinc reagents in high diastereoselectivity

  底物控制的非对映选择性硼氢化反应的范围可以通过硼锌交换反应大大提高，从而提供可与各种亲电试剂反应的有机锌衍生物。甚至通过儿茶酚硼烷经Rh催化的硼氢化反应获得的通常无反应的硼酸酯，也容易与iPr2Zn反应，从而以高非对映选择性提供相应的锌试剂。
• Regio- and Stereospecific Formation of Protected Allylic Alcohols via Zirconium-Mediated S_N2‘ Substitution of Allylic Chlorides
  作者：Richard J. Fox、Gojko Lalic、Robert G. Bergman

  DOI：10.1021/ja075967i

  日期：2007.11.1

  regio- and stereospecific SN2‘ substitution reaction between a zirconium oxo complex and allylic chloride has been achieved. The resulting allylic alcohol or TBS-protected allylic ether products were isolated in good to excellent yields with a wide range of E-allylic chlorides. A mechanism for the SN2‘ allylic substitution consistent with kinetic, stereochemical, and secondary isotope effect studies

  已经实现了锆氧配合物和烯丙基氯之间的新的、高度区域和立体特异性的 SN2' 取代反应。得到的烯丙醇或 TBS 保护的烯丙醚产物与各种 E-烯丙基氯化物以良好至极好的产率分离。提出了与动力学、立体化学和次级同位素效应研究一致的 SN2' 烯丙基取代机制。
• Rhodium(I)-catalyzed hydroboration of olefins. The documentation of regio- and stereochemical control in cyclic and acyclic systems
  作者：David A. Evans、Gregory C. Fu、Amir H. Hoveyda

  DOI：10.1021/ja00228a068

  日期：1988.9

  Catalyse par les complexes Rh(PPh 3 ) 3 Cl et [Rh(nbd)(diphos-4)]BF 4 (nbd=norbornadiene, diphos-4=bis-diphenylphosphino-1,4 butane)

  催化复合物 Rh(PPh 3 ) 3 Cl et [Rh(nbd)(diphos-4)]BF 4 (nbd=降冰片二烯，diphos-4=双-二苯基膦基-1,4丁烷)
• Rhodium(I)- and iridium(I)-catalyzed hydroboration reactions: scope and synthetic applications
  作者：David A. Evans、Gregory C. Fu、Amir H. Hoveyda

  DOI：10.1021/ja00043a009

  日期：1992.8

  A study of the rhodium(1)- and iridium(1)-catalyzed hydroboration of olefins with catecholborane is described. Applications to organic synthesis were one focus of this investigation. The scope of the reaction was defined, and issues of stereoselection were addressed. The rhodium-catalyzed hydroboration of several classes of allylic alcohols was found to be highly diastereoselective, preferentially

  描述了铑 (1)-和铱 (1)-催化烯烃与儿茶酚硼烷硼氢化的研究。有机合成的应用是这项研究的重点之一。定义了反应的范围，并解决了立体选择问题。发现几类烯丙醇的铑催化硼氢化反应具有高度的非对映选择性，优先提供与未催化反应变体 (9-BBN) 提供的异构体互补的异构体。开发了实现定向烯烃硼氢化的前两种通用方法。亚膦酸盐和酰胺都证明能够传递过渡金属试剂。