(2E)-4,5-dihydroxy-2-hexadecenoic acid ethyl ester | 425621-51-8

• 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: (2E)-4,5-dihydroxy-2-hexadecenoic acid ethyl ester
• 英文别名: ethyl (E)-4,5-dihydroxyhexadec-2-enoate
• CAS: 425621-51-8
• 化学式: C₁₈H₃₄O₄
• 分子量: 314.466
• InChiKey: XZAFKWPOFSFVKS-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-4,5-dihydroxy-2-hexadecenoic acid ethyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(2E)-4,5-dioxo-2-hexadecenoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of podoscyphic acid

  摘要：

  Podoscyphic acid 1, a fungal metabolite inhibiting RNA-directed DNA polymerises, was synthesised in four steps starting from dodecanal. The concluding ester hydrolysis of 4 was not feasible with chemical reagents, only enzymatic hydrolysis was mild enough to release the highly reactive natural product in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02264-x
• 作为产物：
  描述：

  十二醛 在 奎宁环 、 甲基磺酰胺 四氧化锇 、 potassium carbonate 、 potassium hexacyanoferrate(III) 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 96.0h， 生成 (2E)-4,5-dihydroxy-2-hexadecenoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of podoscyphic acid

  摘要：

  Podoscyphic acid 1, a fungal metabolite inhibiting RNA-directed DNA polymerises, was synthesised in four steps starting from dodecanal. The concluding ester hydrolysis of 4 was not feasible with chemical reagents, only enzymatic hydrolysis was mild enough to release the highly reactive natural product in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02264-x

文献信息

• Synthesis of podoscyphic acid
  作者：Johan Eriksson、Martin Johansson、Olov Sterner

  DOI：10.1016/s0040-4039(01)02264-x

  日期：2002.1

  Podoscyphic acid 1, a fungal metabolite inhibiting RNA-directed DNA polymerises, was synthesised in four steps starting from dodecanal. The concluding ester hydrolysis of 4 was not feasible with chemical reagents, only enzymatic hydrolysis was mild enough to release the highly reactive natural product in good yields. (C) 2002 Elsevier Science Ltd. All rights reserved.