methyl (2E)-11-(tetrahydropyranyloxy)dodec-2-enoate | 173483-48-2

• 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)-11-(tetrahydropyranyloxy)dodec-2-enoate
• 英文别名: methyl (E)-11-(oxan-2-yloxy)dodec-2-enoate
• CAS: 173483-48-2
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: KEGUMBBGOVOZQI-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2E)-11-(tetrahydropyranyloxy)dodec-2-enoate 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以90%的产率得到methyl (E)-11-hydroxydodec-2-enoate
  参考文献：
  名称：

  Expedient Synthesis of (R)-Patulolide A

  摘要：

  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.

  DOI：

  10.1021/jo951339k
• 作为产物：
  描述：

  10-十一烯-1-醇 在 manganese(IV) oxide 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氰化钠 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 71.0h， 生成 methyl (2E)-11-(tetrahydropyranyloxy)dodec-2-enoate
  参考文献：
  名称：

  Expedient Synthesis of (R)-Patulolide A

  摘要：

  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.

  DOI：

  10.1021/jo951339k

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.