trimethyl-[(Z)-oct-4-en-1,7-diynyl]silane | 1352963-74-6

• 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: trimethyl-[(Z)-oct-4-en-1,7-diynyl]silane
• CAS: 1352963-74-6
• 化学式: C₁₁H₁₆Si
• 分子量: 176.334
• InChiKey: GWEUVSWXIOWPSL-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  trimethyl-[(Z)-oct-4-en-1,7-diynyl]silane 在 盐酸 、 甲醇 、 正丙胺 、 sodium cyanide 、 copper(l) iodide 、 四(三苯基膦)钯 、 水 、 silver nitrate 作用下， 以 甲醇 、 苯 为溶剂， 生成 C₂₃H₃₀O₄
  参考文献：
  名称：

  First total synthesis of the anti-inflammatory lipid mediator Resolvin D6

  摘要：

  The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd-0/Cu-I Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.003
• 作为产物：
  描述：

  (Z)-1,8-bis(trimethylsilyl)octa-4-en-1,7-diyne 在 sodium cyanide 、 水 、 silver nitrate 作用下， 以 甲醇 为溶剂， 生成 trimethyl-[(Z)-oct-4-en-1,7-diynyl]silane
  参考文献：
  名称：

  First total synthesis of the anti-inflammatory lipid mediator Resolvin D6

  摘要：

  The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd-0/Cu-I Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.003

文献信息

• Total synthesis of the anti-inflammatory lipid mediator Resolvin E2
  作者：Ana R. Rodriguez、Bernd W. Spur

  DOI：10.1016/j.tetlet.2012.01.136

  日期：2012.4

  The total synthesis of Resolvin E2, an endogenous lipid mediator of the resolution of inflammation derived from eicosapentaenoic acid, has been achieved. The chiral hydroxy-groups at C5 and C18 were generated in a simple, efficient, and environmentally friendly manner via an asymmetric Noyori transfer hydrogenation in water using sodium formate as a reducing agent. Pd0/CuI Sonogashira couplings of

  已经实现了Resolvin E2的全合成，Resolvin E2是一种可解决二十碳五烯酸的炎症的内源性脂质介质。通过使用甲酸钠作为还原剂在水中进行不对称的Noyori转移加氢，以简单，有效和环保的方式生成C5和C18处的手性羟基。三个关键片段的Pd 0 / Cu I Sonogashira偶联和Zn（Cu / Ag）还原完成了Resolvin E2的合成。