(1R,3S,4S,5R)-6,6-dimethyl-2-oxo-4-(4-trimethylsilylbut-3-yn-1-yl)bicyclo[3.1.1]heptane-3-carbonitrile | 1268673-78-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,3S,4S,5R)-6,6-dimethyl-2-oxo-4-(4-trimethylsilylbut-3-yn-1-yl)bicyclo[3.1.1]heptane-3-carbonitrile
• 英文别名: (1R,3S,4S,5R)-6,6-dimethyl-2-oxo-4-(4-(trimethylsilyl)but-3-ynyl)bicyclo[3.1.1]heptane-3-carbonitrile；(1R,3S,4S,5R)-6,6-dimethyl-2-oxo-4-(4-trimethylsilylbut-3-ynyl)bicyclo[3.1.1]heptane-3-carbonitrile
• CAS: 1268673-78-4
• 化学式: C₁₇H₂₅NOSi
• 分子量: 287.477
• InChiKey: JTIBTRMXIIPPLB-TUVASFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3S,4S,5R)-6,6-dimethyl-2-oxo-4-(4-trimethylsilylbut-3-yn-1-yl)bicyclo[3.1.1]heptane-3-carbonitrile 在 吡啶 、 氧气 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以62%的产率得到8,8-dimethyl-7-oxo-1-((trimethylsilyl)carbonyl)-3,3a,4,5,6,7-hexahydro-4,6-methano-indene-7a-carbonitrile
  参考文献：
  名称：

  Autoxidative Annulation Cascade of the α-Cyano β-TMS-capped Alkynyl Cycloalkanone System

  摘要：

  The autoxidative annulation cascade promoted by an a.-cyano beta-TMS-capped alkynyl cycloalkanone system under catalysis with pyridine in one oxygen atmosphere has proven to be highly viable. On the basis of this newly developed protocol, a variety of highly functionalized bicyclic frameworks can be effectively constructed.

  DOI：

  10.1021/ol102947u
• 作为产物：
  描述：

  (1R,5R)-6,6-dimethyl-4-oxo-bicyclo[3.1.1]hept-2-ene-3-carbonitrile 、 (4-(trimethylsilyl)but-3-ynyl)magnesium chloride 在 三甲基氯硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以74%的产率得到(1R,3S,4S,5R)-6,6-dimethyl-2-oxo-4-(4-trimethylsilylbut-3-yn-1-yl)bicyclo[3.1.1]heptane-3-carbonitrile
  参考文献：
  名称：

  Conia-ene annulation of the α-cyano β-TMS-capped alkynyl cycloalkanone system and its synthetic application

  摘要：

  在 ZnI2 的催化下，开发了一种有效的Ï-硅乙炔基δ-±-氰基酮环化过程，从而形成了以含 TMS 的亚甲基环戊烷环为特征的各种双环框架。

  DOI：

  10.1039/c1ob05591g

文献信息

• Conia-ene annulation of the α-cyano β-TMS-capped alkynyl cycloalkanone system and its synthetic application
  作者：Chih-Lung Chin、Cheng-Feng Liao、Hsing-Jang Liu、Ying-Chieh Wong、Ming-Tsang Hsieh、Prashanth K. Amancha、Chun-Ping Chang、Kak-Shan Shia

  DOI：10.1039/c1ob05591g

  日期：——

  Under catalysis with ZnI2, an effective annulation process of ω-silylacetylenic α-cyano ketones, leading to the formation of various bicyclic frameworks characterized with a TMS-containing methylenecyclopentane ring, has been developed.

  在 ZnI2 的催化下，开发了一种有效的Ï-硅乙炔基δ-±-氰基酮环化过程，从而形成了以含 TMS 的亚甲基环戊烷环为特征的各种双环框架。
• Autoxidative Annulation Cascade of the α-Cyano β-TMS-capped Alkynyl Cycloalkanone System
  作者：Ying-Chieh Wong、Min-Tsang Hsieh、Prashanth K. Amancha、Chih-Lung Chin、Cheng-Feng Liao、Chun-Wei Kuo、Kak-Shan Shia

  DOI：10.1021/ol102947u

  日期：2011.3.4

  The autoxidative annulation cascade promoted by an a.-cyano beta-TMS-capped alkynyl cycloalkanone system under catalysis with pyridine in one oxygen atmosphere has proven to be highly viable. On the basis of this newly developed protocol, a variety of highly functionalized bicyclic frameworks can be effectively constructed.