methyl (2E,11R)-11-acetoxy-4-oxododec-2-enoate | 228109-68-0

• 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: methyl (2E,11R)-11-acetoxy-4-oxododec-2-enoate
• 英文别名: methyl (E,11R)-11-acetyloxy-4-oxododec-2-enoate
• CAS: 228109-68-0
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: ZQUBTLZPYXZYKH-HCRIHEDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2E,11R)-11-acetoxy-4-oxododec-2-enoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 以95%的产率得到(4E,11R)-11-hydroxy-4-oxo-2-dodecenoic acid
  参考文献：
  名称：

  Total synthesis of R-(+)-patulolide A and R-(−)-patulolide B: The macrolides isolated from Penicillium urticae mutant

  摘要：

  The title compounds (2E,11R)-4-oxo-2-dodecen-11-olide, 1 and (2Z,11R)-4-oxo-2-dodecen-11-olide, 2 were synthesised in optically pure forms from a nitroalkane synthon involving a chiral resolution step using goat liver lipase. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00164-7
• 作为产物：
  描述：

  (+/-)-9-nitrononan-2-ol 在 potassium fluoride 、 titanium(III) chloride 、 goat liver lipase 、 ammonium acetate 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 52.5h， 生成 methyl (2E,11R)-11-acetoxy-4-oxododec-2-enoate
  参考文献：
  名称：

  Total synthesis of R-(+)-patulolide A and R-(−)-patulolide B: The macrolides isolated from Penicillium urticae mutant

  摘要：

  The title compounds (2E,11R)-4-oxo-2-dodecen-11-olide, 1 and (2Z,11R)-4-oxo-2-dodecen-11-olide, 2 were synthesised in optically pure forms from a nitroalkane synthon involving a chiral resolution step using goat liver lipase. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00164-7

文献信息

• Expedient Synthesis of (<i>R</i>)-Patulolide A
  作者：A. Sharma、S. Sankaranarayanan、S. Chattopadhyay

  DOI：10.1021/jo951339k

  日期：1996.1.1

  An efficient derivation of the title compound has been formulated from easily accessible 10-undecenoic acid(1). Thus, dodec-11-en-2-ol (3), prepared from 1, was pyranylated and subjected to bromination with NBS followed by acetolysis to furnish (2E)-1-acetoxy-11-(tetrahydropyranyloxy)-dodec-2-ene (5). Its hydrolysis, oxidation, and depyranylation afforded the (2E)-hydroxy ester (9). This, on Candida rugosa lipase-catalyzed acetylation, SeO2 oxidation, hydrolysis, and Yamaguchi macrolactonization, led to (R)-patulolide A (I) with 67.1% ee. The enantiomeric excess was improved to 97% by first resolving the alcohol 3 via porcine pancreatic lipase catalyzed acetylation and converting the corresponding (R)-acetate (13) to I as done above.