1-trimethylsilyloxy-2-azido octane

• 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-trimethylsilyloxy-2-azido octane
• 英文别名: 2-Azidooctoxy(trimethyl)silane
• 化学式: C₁₁H₂₅N₃OSi
• 分子量: 243.424
• InChiKey: WAOZRRVYXQWQLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  叠氮基三甲基硅烷 、 1,2-环氧辛烷 在 aluminum isopropoxide 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以74%的产率得到1-azido-2-(trimethylsilyloxy)octane
  参考文献：
  名称：

  A Highly Regio- and Chemoselective Ring Opening of Epoxides with Trimethylsilyl Azide/Aluminum Isopropoxide

  摘要：

  功能化环氧化物通过三甲基硅基叠氮化钠/异丙醇铝选择性地对位打开，生成2-三甲基硅氧基叠氮化物，攻击的是取代基较少的碳原子。

  DOI：

  10.1055/s-1988-27631

文献信息

• A Highly Regio- and Chemoselective Ring Opening of Epoxides with Trimethylsilyl Azide/Aluminum Isopropoxide
  作者：M. Emziane、P. Lhoste、D. Sinou

  DOI：10.1055/s-1988-27631

  日期：——

  Functionalized epoxides are regioselectively opened using trimethylsilyl azide/aluminum isopropoxide giving 2-trimethylsiloxy azides by attack on the less substituted carbon.

  功能化环氧化物通过三甲基硅基叠氮化钠/异丙醇铝选择性地对位打开，生成2-三甲基硅氧基叠氮化物，攻击的是取代基较少的碳原子。
• Highly regio and chemoselective ring opening of epoxides with trimethylsilyl azide in the presence of aluminium isopropoxide and titanium isopropoxide
  作者：Kun I. Sutowardoyo、Mohamed Emziane、Paul Lhoste、Denis Sinou

  DOI：10.1016/s0040-4020(01)86420-6

  日期：1991.1

  The ring-opening of functionalized epoxides with trimethylsilyl azide in the presence of a catalytic amount of Ti(O-i-Pr)4 or Al(O-i-Pr)3 is described. The reaction is stereospecific and highly regiospecific, leading generally to the formation of the carbon-azido bond on the less substituted carbon. The mechanism of this reaction is also discussed.
• Scope and limitations of one-pot multistep reactions with heterogeneous catalysts: The case of alkene epoxidation coupled to epoxide ring-opening
  作者：José M. Fraile、Nuria García、Clara I. Herrerías、José A. Mayoral

  DOI：10.1016/j.cattod.2011.03.067

  日期：2011.9

  The combination of two reactions in one-pot multistep system requires the compatibility not only between the catalysts of both reactions, but also between all the reaction components and conditions. In the case of the coupling of alkene epoxidation and epoxide ring opening, it has been possible to synthesize cyanohydrin and azidohydrin derivatives through a simple process that involves a one-pot multistep process by using a mixture of two heterogeneous catalysts, a silica-grafted Ti catalyst and ytterbium chloride, whose efficiency depends on the reactivity of the starting alkene. In addition, in some cases the mixture of catalysts can be recovered and reused in several one-pot multistep cycles. However, this system is not possible with electron- deficient alkenes, as the basic catalyst required for epoxidation has shown to be incompatible with the ring-opening process. (C) 2011 Elsevier B.V. All rights reserved.
• Ouverture régiosélective d'époxydes par Me3SiN3 catalysée par Ti[O.iPr]4
  作者：Denis Sinou、Mohamed Emziane

  DOI：10.1016/s0040-4039(00)84968-0

  日期：1986.1
• Ring opening reactions of epoxides catalyzed by samarium iodides
  作者：Pierre Van de Weghe、Jacqueline Collin

  DOI：10.1016/0040-4039(95)00086-r

  日期：1995.3

  SmI2(THF)(2) catalyzes the ring opening of epoxides by trimethylsilylazide, trimethylsilylcyanide and primary and secondary amines. High regioselectivities are observed in specific cases.