(3E,7R,8S)-7,8-epoxycosa-1,3-diene | 1008751-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (3E,7R,8S)-7,8-epoxycosa-1,3-diene
• 英文别名: (2S,3R)-2-dodecyl-3-[(3E)-hexa-3,5-dienyl]oxirane
• CAS: 1008751-11-8
• 化学式: C₂₀H₃₆O
• 分子量: 292.505
• InChiKey: XWNZAYZRNAFPRC-LVHMURGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  21
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3E,7R,8S)-7,8-epoxycosa-1,3-diene 在 甲基磺酰胺 、 AD-mix β 作用下， 以 水 、 叔丁醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of solamin type mono-THF acetogenins using cross-metathesis

  摘要：

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.028
• 作为产物：
  描述：

  (1R,2'R)-1-(5'-hydroxytetrahydrofuran-2'-yl)tridecyl methanesulfonate 、 烯丙基磷酸二乙酯 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以64%的产率得到(3E,7R,8S)-7,8-epoxycosa-1,3-diene
  参考文献：
  名称：

  Synthesis of solamin type mono-THF acetogenins using cross-metathesis

  摘要：

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.028

文献信息

• Synthesis of solamin type mono-THF acetogenins using cross-metathesis
  作者：Hiroyuki Konno、Hidefumi Makabe、Yasunao Hattori、Kazuto Nosaka、Kenichi Akaji

  DOI：10.1016/j.tet.2010.08.028

  日期：2010.10

  The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and gamma-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure gamma-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. (C) 2010 Elsevier Ltd. All rights reserved.