(2Z,4E)-methyl heptadeca-2,4-dienoate | 910452-46-9

• 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: (2Z,4E)-methyl heptadeca-2,4-dienoate
• 英文别名: methyl (2Z,4E)-heptadeca-2,4-dienoate
• CAS: 910452-46-9
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: MNDHVJPEFKRLKH-FZIQOSRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  (2Z,4E)-methyl heptadeca-2,4-dienoate 在 palladium on activated charcoal 、 potassium carbonate 、 potassium hexacyanoferrate(III) 四氧化锇 、 Hydroquinone 1,4-phthalazinediyl diether 、 甲基磺酰胺 、 氢气 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 24.0h， 生成 (+)-muricatacin
  参考文献：
  名称：

  De Novo Asymmetric Syntheses of Muricatacin and Its Analogues via Dihydroxylation of Dienoates

  摘要：

  A short and highly efficient route to both enantiomers of muricatacin as well as the C-5-epimer has been developed. The key to the overall transformation is the highly regio- and enantioselective Sharpless asymmetric dihydroxylation of an (E,Z)-dienoate. The highly efficient stereoselective synthesis prepares (-)-muricatacin in seven steps and 66% overall yield.

  DOI：

  10.1021/jo061057s
• 作为产物：
  描述：

  2-tetradecenoic acid ethyl ester 在 manganese(IV) oxide 、 18-冠醚-6 、 potassium tert-butylate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 27.0h， 生成 (2Z,4E)-methyl heptadeca-2,4-dienoate
  参考文献：
  名称：

  De Novo Asymmetric Syntheses of Muricatacin and Its Analogues via Dihydroxylation of Dienoates

  摘要：

  A short and highly efficient route to both enantiomers of muricatacin as well as the C-5-epimer has been developed. The key to the overall transformation is the highly regio- and enantioselective Sharpless asymmetric dihydroxylation of an (E,Z)-dienoate. The highly efficient stereoselective synthesis prepares (-)-muricatacin in seven steps and 66% overall yield.

  DOI：

  10.1021/jo061057s

文献信息

• De Novo Asymmetric Syntheses of Muricatacin and Its Analogues via Dihydroxylation of Dienoates
  作者：Md. Moinuddin Ahmed、Hu Cui、George A. O'Doherty

  DOI：10.1021/jo061057s

  日期：2006.8.1

  A short and highly efficient route to both enantiomers of muricatacin as well as the C-5-epimer has been developed. The key to the overall transformation is the highly regio- and enantioselective Sharpless asymmetric dihydroxylation of an (E,Z)-dienoate. The highly efficient stereoselective synthesis prepares (-)-muricatacin in seven steps and 66% overall yield.