1,1-Di-tert-butyl-2-(2-triisopropylsilanyloxy-ethyl)-silirane | 326499-52-9

• 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-Di-tert-butyl-2-(2-triisopropylsilanyloxy-ethyl)-silirane
• 英文别名: 2-(1,1-Ditert-butylsiliran-2-yl)ethoxy-tri(propan-2-yl)silane
• CAS: 326499-52-9
• 化学式: C₂₁H₄₆OSi₂
• 分子量: 370.767
• InChiKey: ZKFKNVXEAJUTTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  甲酸甲酯 、 1,1-Di-tert-butyl-2-(2-triisopropylsilanyloxy-ethyl)-silirane 在 zinc dibromide 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以0.196 g的产率得到(S)-3-(2-Benzyloxy-ethyl)-2,2-di-tert-butyl-5-methoxy-[1,2]oxasilolane
  参考文献：
  名称：

  Metal-Catalyzed Silacyclopropanation of Mono- and Disubstituted Alkenes

  摘要：

  As an alternative to the strongly reducing conditions necessary for the formation of silacyclopropanes, silylene transfer was developed as a mild, functional group tolerant method of silacyclopropanation. Complex silacyclopropanes were formed from functionalized alkenes using cyclohexane di-tert-butyl silacyclopropane, 1, as the source of t-Bu(2)Si. Di-tert-butyl silylene can be generated from 1 through the use of a catalytic amount of a metal salt. At -27 degrees C, silver triflate catalyzes the transfer of t-Bu(2)Si from 1 to mono- and disubstituted alkenes stereospecifically and diastereoselectively. In situ functionalization of silacyclopropanes with catalytic zinc bromide and methyl formate provides for an expedient one-flask synthesis of complex oxasilacyclopentanes from alkenes.

  DOI：

  10.1021/ja020566i
• 作为产物：
  描述：

  三异丙基氯硅烷 在 咪唑 、 silver trifluoromethanesulfonate 作用下， 以 氘代甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1,1-Di-tert-butyl-2-(2-triisopropylsilanyloxy-ethyl)-silirane
  参考文献：
  名称：

  Metal-Catalyzed Silacyclopropanation of Mono- and Disubstituted Alkenes

  摘要：

  As an alternative to the strongly reducing conditions necessary for the formation of silacyclopropanes, silylene transfer was developed as a mild, functional group tolerant method of silacyclopropanation. Complex silacyclopropanes were formed from functionalized alkenes using cyclohexane di-tert-butyl silacyclopropane, 1, as the source of t-Bu(2)Si. Di-tert-butyl silylene can be generated from 1 through the use of a catalytic amount of a metal salt. At -27 degrees C, silver triflate catalyzes the transfer of t-Bu(2)Si from 1 to mono- and disubstituted alkenes stereospecifically and diastereoselectively. In situ functionalization of silacyclopropanes with catalytic zinc bromide and methyl formate provides for an expedient one-flask synthesis of complex oxasilacyclopentanes from alkenes.

  DOI：

  10.1021/ja020566i

文献信息

• Metal-Catalyzed Di-<i>tert-</i>butylsilylene Transfer:  Synthesis and Reactivity of Silacyclopropanes
  作者：Jelena Ćiraković、Tom G. Driver、K. A. Woerpel

  DOI：10.1021/jo0355505

  日期：2004.6.1

  developed as a mild, operationally simple, functional-group-tolerant method for silacyclopropane formation. Di-tert-butylsilylene was transferred from cyclohexene silacyclopropane 1 to an alkene through the use of a metal salt. Silacyclopropanation occurred at temperatures as low as −27 °C when AgOTf or AgOC(O)CF3 were used as catalysts. Complex silacyclopropanes were formed stereospecifically and

  金属催化的二叔丁基亚甲硅烷基转移反应是一种温和的，操作简便的，官能团耐受的硅环丙烷形成方法。通过使用金属盐将二叔丁基亚甲硅烷基从环己烯硅环丙烷1转移至烯烃。当将AgOTf或AgOC（O）CF 3用作催化剂时，硅环丙烷化发生在低至-27°C的温度下。复杂的硅杂环丙烷是由官能化烯烃立体定向和非对映选择性地形成的。在整个过程中，硅环丙烷与各种羰基化合物（包括醛，酮，甲酸酯和甲酰胺）反应，可以有效地将烯烃转化为具有定义立体化学的氧杂硅环戊烷。
• ZnBr2-Catalyzed Insertions of Carbonyl Compounds into Silacyclopropanes: Regiochemical Reversal Dependent on Metal Salt
  作者：Annaliese K. Franz、K. A. Woerpel

  DOI：10.1002/1521-3773(20001201)39:23<4295::aid-anie4295>3.0.co;2-a

  日期：2000.12.1
• Metal-Catalyzed Silacyclopropanation of Mono- and Disubstituted Alkenes
  作者：Jelena Ćiraković、Tom G. Driver、K. A. Woerpel

  DOI：10.1021/ja020566i

  日期：2002.8.1

  As an alternative to the strongly reducing conditions necessary for the formation of silacyclopropanes, silylene transfer was developed as a mild, functional group tolerant method of silacyclopropanation. Complex silacyclopropanes were formed from functionalized alkenes using cyclohexane di-tert-butyl silacyclopropane, 1, as the source of t-Bu(2)Si. Di-tert-butyl silylene can be generated from 1 through the use of a catalytic amount of a metal salt. At -27 degrees C, silver triflate catalyzes the transfer of t-Bu(2)Si from 1 to mono- and disubstituted alkenes stereospecifically and diastereoselectively. In situ functionalization of silacyclopropanes with catalytic zinc bromide and methyl formate provides for an expedient one-flask synthesis of complex oxasilacyclopentanes from alkenes.