(2S,3E)-methyl 2,4-dimethyltetradec-3-enoate | 223726-40-7

• 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)-methyl 2,4-dimethyltetradec-3-enoate
• 英文别名: methyl (E,2S)-2,4-dimethyltetradec-3-enoate
• CAS: 223726-40-7
• 化学式: C₁₇H₃₂O₂
• 分子量: 268.44
• InChiKey: CSQYTIWWDXTIDL-IYOXOMEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (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
• 作为产物：
  描述：

  1-十二炔 、 methyl (S)-2-[(trifluoromethanesulfonyl)oxy]propionate 在 二氯二茂锆 、 甲基锂 、 三甲基铝 作用下， 生成 (2S,3E)-methyl 2,4-dimethyltetradec-3-enoate
  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.