(E)-ethyl 14,14-dibromotetradeca-2,13-dienoate | 1215102-24-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-ethyl 14,14-dibromotetradeca-2,13-dienoate
• 英文别名: ethyl (2E)-14,14-dibromotetradeca-2,13-dienoate
• CAS: 1215102-24-1
• 化学式: C₁₆H₂₆Br₂O₂
• 分子量: 410.189
• InChiKey: IYDCWEFESAMILL-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 14,14-dibromotetradeca-2,13-dienoate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 以72%的产率得到Motualevic Acid E
  参考文献：
  名称：

  Total synthesis of motualevic acids A–F, (E) and (Z)-antazirines

  摘要：

  Total synthesis of motualevic acids A-F and (E) & (Z) geometrical isomers of antazirines has been achieved from a commercially available starting material, 1,10-decanediol. The synthesis of motualevic acid E served as a common key intermediate for the synthesis of most of these natural products. The key steps involved in this synthesis were Wittig olefination, Corey-Fuchs reaction, Neber reaction, amide coupling. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.092
• 作为产物：
  描述：

  10-溴-1-癸醇 在 草酰氯 、 18-冠醚-6 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 对甲苯磺酸 、 二甲基亚砜 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 80.83h， 生成 (E)-ethyl 14,14-dibromotetradeca-2,13-dienoate
  参考文献：
  名称：

  Total synthesis of motualevic acids A–F, (E) and (Z)-antazirines

  摘要：

  Total synthesis of motualevic acids A-F and (E) & (Z) geometrical isomers of antazirines has been achieved from a commercially available starting material, 1,10-decanediol. The synthesis of motualevic acid E served as a common key intermediate for the synthesis of most of these natural products. The key steps involved in this synthesis were Wittig olefination, Corey-Fuchs reaction, Neber reaction, amide coupling. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.092

文献信息

• Total synthesis of motualevic acids A–E
  作者：Gangarajula Sudhakar、Vilas D. Kadam、Vaddu V.N. Reddy

  DOI：10.1016/j.tetlet.2009.12.113

  日期：2010.2

  The first total synthesis of motualevic acids A-E, isolated from Siliquariaspongia sp., starting from commercially available 1,10-decanediol, is described. The key steps in the synthetic sequence involve stereoselective olefination, Corey-Fuchs reaction, and amide coupling. (C) 2010 Published by Elsevier Ltd.
• Total synthesis of motualevic acids A–F, (E) and (Z)-antazirines
  作者：Vilas D. Kadam、Gangarajula Sudhakar

  DOI：10.1016/j.tet.2014.12.092

  日期：2015.2

  Total synthesis of motualevic acids A-F and (E) & (Z) geometrical isomers of antazirines has been achieved from a commercially available starting material, 1,10-decanediol. The synthesis of motualevic acid E served as a common key intermediate for the synthesis of most of these natural products. The key steps involved in this synthesis were Wittig olefination, Corey-Fuchs reaction, Neber reaction, amide coupling. (C) 2014 Elsevier Ltd. All rights reserved.