3,3-Dimethylbut-1-ynyl-diphenyl-prop-2-enylsilane | 909805-48-7

• 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: 3,3-Dimethylbut-1-ynyl-diphenyl-prop-2-enylsilane
• 英文别名: 3,3-dimethylbut-1-ynyl-diphenyl-prop-2-enylsilane
• CAS: 909805-48-7
• 化学式: C₂₁H₂₄Si
• 分子量: 304.507
• InChiKey: QCJAHPBCBWLBIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3,3-Dimethylbut-1-ynyl-diphenyl-prop-2-enylsilane 、 9-borabicyclo[3.3.1]nonane 以 甲苯 为溶剂， 生成 9-Borabicyclo[3.3.1]nonane,9-[2-(1,1-dimethylethyl)-1,1-dimethylsilacyclohex-2-en-3-yl]-
  参考文献：
  名称：

  An efficient route to substituted 1-silacyclopent-2-enes and 1-silacyclohex-2-enes via consecutive 1,2-hydroboration and 1,1-organoboration

  摘要：

  The reaction of alkyn-1-yl(vinyl)silanes R2Si(C CR1)CH=CH2[R = Me (1), Ph (2); R-1 = Bu-t (a), Ph (b), SiMe3 (c)] with 9-borabicyclo[3.3.1]nonane in a 1:1 ratio affords the 1-silacyclopent-2-ene derivatives 4a-c (R = Me) and 5a-c (R = Ph) as a result of selective intermolecular 1,2-hydroboration. of the vinyl group, followed by intramolecular 1, 1-organoboration of the alkynyl substituent. The analogous reaction sequence converts the alkyn-1-yl(allyl)dimethylsilanes 3a,c into the 1-silacyclohex-2-ene derivatives 7a,c. All reactions were monitored by Si-29 NMR spectroscopy and the structural assignment of the final products was based on multinuclear magnetic resonance data (H-1, B-11, C-13 and Si-29 NMR). The molecular structure of 6a was determined by X-ray analysis. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2005.03.016
• 作为产物：
  描述：

  二苯基二甲氧基硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 3.0h， 生成 3,3-Dimethylbut-1-ynyl-diphenyl-prop-2-enylsilane
  参考文献：
  名称：

  Gold-Catalyzed Intramolecular Allylation of Silyl Alkynes Induced by Silane Alcoholysis

  摘要：

  The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.

  DOI：

  10.1021/ja062560p

文献信息

• Gold-Catalyzed Intramolecular Allylation of Silyl Alkynes Induced by Silane Alcoholysis
  作者：Sangho Park、Daesung Lee

  DOI：10.1021/ja062560p

  日期：2006.8.1

  The activation of alkynyl allyl silanes with a cationic gold catalyst in the presence of alcohols provides vinyl silanes that contain the allyl group at the beta-position and the alkoxysilyl group in cis-orientation. The bond reorganization process is most consistent with the involvement of a carbocationic intermediate, which undergoes a nucleophilic attack by an alcohol selectively at the silicon center. The cis-vinyl silyl ether products can be further elaborated by ring-closing and cross metathesis to form more substituted 1,4-dienyl silanes.
• An efficient route to substituted 1-silacyclopent-2-enes and 1-silacyclohex-2-enes via consecutive 1,2-hydroboration and 1,1-organoboration
  作者：Bernd Wrackmeyer、Oleg L. Tok、Rhett Kempe

  DOI：10.1016/j.ica.2005.03.016

  日期：2005.11

  The reaction of alkyn-1-yl(vinyl)silanes R2Si(C CR1)CH=CH2[R = Me (1), Ph (2); R-1 = Bu-t (a), Ph (b), SiMe3 (c)] with 9-borabicyclo[3.3.1]nonane in a 1:1 ratio affords the 1-silacyclopent-2-ene derivatives 4a-c (R = Me) and 5a-c (R = Ph) as a result of selective intermolecular 1,2-hydroboration. of the vinyl group, followed by intramolecular 1, 1-organoboration of the alkynyl substituent. The analogous reaction sequence converts the alkyn-1-yl(allyl)dimethylsilanes 3a,c into the 1-silacyclohex-2-ene derivatives 7a,c. All reactions were monitored by Si-29 NMR spectroscopy and the structural assignment of the final products was based on multinuclear magnetic resonance data (H-1, B-11, C-13 and Si-29 NMR). The molecular structure of 6a was determined by X-ray analysis. (c) 2005 Elsevier B.V. All rights reserved.