(5R,6R)-5-ethyl-2,2,3,3,8,8,9,9-octamethyl-6-((1E,3E)-6-(trimethylsilyl)hexa-1,3-dien-5-yn-1-yl)-4,7-dioxa-3,8-disiladecane | 1360805-81-7

• 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: (5R,6R)-5-ethyl-2,2,3,3,8,8,9,9-octamethyl-6-((1E,3E)-6-(trimethylsilyl)hexa-1,3-dien-5-yn-1-yl)-4,7-dioxa-3,8-disiladecane
• CAS: 1360805-81-7
• 化学式: C₂₅H₅₀O₂Si₃
• 分子量: 466.927
• InChiKey: MWIRRBRYBNOPMR-XDZBSOFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.17
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (5R,6R)-5-ethyl-2,2,3,3,8,8,9,9-octamethyl-6-((1E,3E)-6-(trimethylsilyl)hexa-1,3-dien-5-yn-1-yl)-4,7-dioxa-3,8-disiladecane 在 copper(l) iodide 、 potassium carbonate 、 caesium carbonate 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.55h， 生成 (5R,6R)-5-((1E,3E)-15-(1,3-dioxolan-2-yl)pentadeca-1,3-dien-5,8,11-triyn-1-yl)-6-ethyl-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane
  参考文献：
  名称：

  Total syntheses of four possible stereoisomers of resolvin E3

  摘要：

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.045
• 作为产物：
  描述：

  methyl (2S,3R)-2,3-bis((tert-butyldimethylsilyl)oxy)pentanoate 在 正丁基锂 、 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.17h， 生成 (5R,6R)-5-ethyl-2,2,3,3,8,8,9,9-octamethyl-6-((1Z,3E)-6-(trimethylsilyl)hexa-1,3-dien-5-yn-1-yl)-4,7-dioxa-3,8-disiladecane 、 (5R,6R)-5-ethyl-2,2,3,3,8,8,9,9-octamethyl-6-((1E,3E)-6-(trimethylsilyl)hexa-1,3-dien-5-yn-1-yl)-4,7-dioxa-3,8-disiladecane
  参考文献：
  名称：

  Total syntheses of four possible stereoisomers of resolvin E3

  摘要：

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.045