[(4S,5E,7Z)-9-bromo-1-(1,3-dioxolan-2-yl)nona-5,7-dien-4-yl]oxy-tert-butyl-dimethylsilane | 1184833-35-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: [(4S,5E,7Z)-9-bromo-1-(1,3-dioxolan-2-yl)nona-5,7-dien-4-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1184833-35-9
• 化学式: C₁₈H₃₃BrO₃Si
• 分子量: 405.448
• InChiKey: WSRDAPXNYDYRNU-HKSFZPIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.43
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(3R,4E,6Z)-deca-4,6-dien-9-yn-3-yl]oxy-dimethylsilane 、 [(4S,5E,7Z)-9-bromo-1-(1,3-dioxolan-2-yl)nona-5,7-dien-4-yl]oxy-tert-butyl-dimethylsilane 在 正丁基锂 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 正己烷 、 六甲基磷酰三胺 为溶剂， 反应 17.08h， 以53%的产率得到tert-butyl-[(3R,4E,6Z,12Z,14E,16S)-16-[tert-butyl(dimethyl)silyl]oxy-19-(1,3-dioxolan-2-yl)nonadeca-4,6,12,14-tetraen-9-yn-3-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Total Synthesis and Bioactivity of Resolvin E2

  摘要：

  Resolvin E2 is a potent anti-inflammatory compound, derived from eicosapentaenoic acid. The efficient total synthesis of resolvin E2 by taking advantage of its intrinsic pseudoenantiomeric substructures is reported. The synthetic resolvin E2 proved to be biologically active in blocking neutrophil Infiltration and reducing proinflammatory cytokines in the acute peritonitis model.

  DOI：

  10.1021/ol901350g
• 作为产物：
  描述：

  在 四溴化碳 、 1,2-双(二苯基膦)乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以100%的产率得到[(4S,5E,7Z)-9-bromo-1-(1,3-dioxolan-2-yl)nona-5,7-dien-4-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Total Synthesis and Bioactivity of Resolvin E2

  摘要：

  Resolvin E2 is a potent anti-inflammatory compound, derived from eicosapentaenoic acid. The efficient total synthesis of resolvin E2 by taking advantage of its intrinsic pseudoenantiomeric substructures is reported. The synthetic resolvin E2 proved to be biologically active in blocking neutrophil Infiltration and reducing proinflammatory cytokines in the acute peritonitis model.

  DOI：

  10.1021/ol901350g

文献信息

• Total Synthesis and Bioactivity of Resolvin E2
  作者：Seiji Ogawa、Daisuke Urabe、Yoshiyuki Yokokura、Hiroyuki Arai、Makoto Arita、Masayuki Inoue

  DOI：10.1021/ol901350g

  日期：2009.8.20

  Resolvin E2 is a potent anti-inflammatory compound, derived from eicosapentaenoic acid. The efficient total synthesis of resolvin E2 by taking advantage of its intrinsic pseudoenantiomeric substructures is reported. The synthetic resolvin E2 proved to be biologically active in blocking neutrophil Infiltration and reducing proinflammatory cytokines in the acute peritonitis model.