(2S,3E)-2,4-dimethyltetradec-3-enoic acid | 223726-41-8

• 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: (2S,3E)-2,4-dimethyltetradec-3-enoic acid
• 英文别名: (E,2S)-2,4-dimethyltetradec-3-enoic acid
• CAS: 223726-41-8
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: IOPRDHRFZNAXSF-BUYIWHAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  R(+)-alpha-甲基苄胺 、 (2S,3E)-2,4-dimethyltetradec-3-enoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到(R)-N-(α-methylbenzyl)-(2S,3E)-2,4-dimethyltetradec-3-enamide
  参考文献：
  名称：

  Synthesis of Elenic Acid, an Inhibitor of Topoisomerase II

  摘要：

  A short, efficient synthesis of elenic acid, a marine natural product with interesting biological activity, has been completed. Critical features of the synthesis are the development of methodology for the one-pot elaboration of an alkyne to an (E)-beta,gamma-unsaturated ester with a stereocenter at the alpha-position and the use of the zipper reaction of a 1-arylalkyne. This reaction has not been previously reported with aromatic substrates. The synthesis strategy provides considerable flexibility for the preparation of structural analogues.

  DOI：

  10.1021/jo982260t
• 作为产物：
  描述：

  (2S,3E)-methyl 2,4-dimethyltetradec-3-enoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以73%的产率得到(2S,3E)-2,4-dimethyltetradec-3-enoic acid
  参考文献：
  名称：

  Synthesis of Elenic Acid, an Inhibitor of Topoisomerase II

  摘要：

  A short, efficient synthesis of elenic acid, a marine natural product with interesting biological activity, has been completed. Critical features of the synthesis are the development of methodology for the one-pot elaboration of an alkyne to an (E)-beta,gamma-unsaturated ester with a stereocenter at the alpha-position and the use of the zipper reaction of a 1-arylalkyne. This reaction has not been previously reported with aromatic substrates. The synthesis strategy provides considerable flexibility for the preparation of structural analogues.

  DOI：

  10.1021/jo982260t

文献信息

• Synthesis of Elenic Acid, an Inhibitor of Topoisomerase II
  作者：Rebecca C. Hoye、Alejandro S. Baigorria、Michael E. Danielson、Alexa A. Pragman、Hemaka A. Rajapakse

  DOI：10.1021/jo982260t

  日期：1999.4.1

  A short, efficient synthesis of elenic acid, a marine natural product with interesting biological activity, has been completed. Critical features of the synthesis are the development of methodology for the one-pot elaboration of an alkyne to an (E)-beta,gamma-unsaturated ester with a stereocenter at the alpha-position and the use of the zipper reaction of a 1-arylalkyne. This reaction has not been previously reported with aromatic substrates. The synthesis strategy provides considerable flexibility for the preparation of structural analogues.