({(E)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-iodo-propenyl}-dimethyl-silanyl)-benzene | 500591-03-7

• 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: ({(E)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-iodo-propenyl}-dimethyl-silanyl)-benzene
• 英文别名: tert-butyl-[(E)-3-[dimethyl(phenyl)silyl]-5-iodopent-3-enoxy]-dimethylsilane
• CAS: 500591-03-7
• 化学式: C₁₉H₃₃IOSi₂
• 分子量: 460.546
• InChiKey: WPTYGVKGVAOLSK-QGOAFFKASA-N

物化性质

• 沸点：
  416.9±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  ({(E)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-iodo-propenyl}-dimethyl-silanyl)-benzene 在 N,N-二甲基丙烯基脲 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,3S,6R,8aR)-3-[tert-butyl(dimethyl)silyl]oxy-6-[(E)-5-[tert-butyl(dimethyl)silyl]oxy-3-[dimethyl(phenyl)silyl]pent-2-enyl]-6,8a-dimethyl-1-propan-2-yl-2,3,7,8-tetrahydro-1H-azulen-5-one
  参考文献：
  名称：

  Formal Synthesis of (±)-Guanacastepene A

  摘要：

  A 17 step synthesis of 55, a late intermediate in Danishefsky's guanacastepene A synthesis, has been completed in 4% overall yield. Key features include the use of vinylmagnesium bromide in the Pd-catalyzed coupling with triflate 13 to give triene 16 without the formation of Heck products, a novel extension of the Stork-Jung vinylsilane Robinson annulation that provides tricyclic 2-hydroxymethylcyclohexenone 42 from 23b in four steps and 51% yield, the ability to obtain almost exclusively alpha'-alkylation of 35ba by the proper choice of protecting groups, and the ability to obtain the desired -alcohol selectively by reduction of keto alcohol 42 rather than keto ester 53.

  DOI：

  10.1021/jo026702j
• 作为产物：
  描述：

  Methanesulfonic acid (E)-5-(tert-butyl-dimethyl-silanyloxy)-3-(dimethyl-phenyl-silanyl)-pent-2-enyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 0.25h， 生成 ({(E)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-iodo-propenyl}-dimethyl-silanyl)-benzene
  参考文献：
  名称：

  Formal Synthesis of (±)-Guanacastepene A

  摘要：

  A 17 step synthesis of 55, a late intermediate in Danishefsky's guanacastepene A synthesis, has been completed in 4% overall yield. Key features include the use of vinylmagnesium bromide in the Pd-catalyzed coupling with triflate 13 to give triene 16 without the formation of Heck products, a novel extension of the Stork-Jung vinylsilane Robinson annulation that provides tricyclic 2-hydroxymethylcyclohexenone 42 from 23b in four steps and 51% yield, the ability to obtain almost exclusively alpha'-alkylation of 35ba by the proper choice of protecting groups, and the ability to obtain the desired -alcohol selectively by reduction of keto alcohol 42 rather than keto ester 53.

  DOI：

  10.1021/jo026702j