(E)-9-Furan-2-yl-3-methanesulfonyloxy-non-8-enoic acid methyl ester | 154224-36-9

• 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: (E)-9-Furan-2-yl-3-methanesulfonyloxy-non-8-enoic acid methyl ester
• CAS: 154224-36-9
• 化学式: C₁₅H₂₂O₆S
• 分子量: 330.402
• InChiKey: HYOGLTMWAKUOBW-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  22.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82.81
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (E)-9-Furan-2-yl-3-methanesulfonyloxy-non-8-enoic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 3.0h， 以73%的产率得到methyl (2E,8E)-9-(2-furyl)nona-2,8-dienoate
  参考文献：
  名称：

  Intramolecular Diels–Alder reactions of vinylfurans leading to furanodecalins

  摘要：

  Thermolysis of the (2E,8Z)-9-(2-furyl)nonadienoate 25 at 290-degrees-C leads to an essentially quantitative yield of a single furanodecalin 26, whereas the corresponding (2E,8E)-isomer 34 undergoes a non-stereoselective cyclisation leading to the furanodecalins 26 and 35. (Z)-Alkenoate functions undergo partial isomerisation prior to cyclisation and so lead to mixtures of isomers. Alkyl groups can be incorporated around the reaction sites, but this can result in overwhelming competition from side reactions. The corresponding 3-furyl analogues 56 and 59 display very similar reactivities.

  DOI：

  10.1039/p19930002395
• 作为产物：
  描述：

  (E)-5-(furan-2-yl)pent-4-en-1-ol 在 吡啶 、 sodium tetrahydroborate 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 21.25h， 生成 (E)-9-Furan-2-yl-3-methanesulfonyloxy-non-8-enoic acid methyl ester
  参考文献：
  名称：

  Intramolecular Diels–Alder reactions of vinylfurans leading to furanodecalins

  摘要：

  Thermolysis of the (2E,8Z)-9-(2-furyl)nonadienoate 25 at 290-degrees-C leads to an essentially quantitative yield of a single furanodecalin 26, whereas the corresponding (2E,8E)-isomer 34 undergoes a non-stereoselective cyclisation leading to the furanodecalins 26 and 35. (Z)-Alkenoate functions undergo partial isomerisation prior to cyclisation and so lead to mixtures of isomers. Alkyl groups can be incorporated around the reaction sites, but this can result in overwhelming competition from side reactions. The corresponding 3-furyl analogues 56 and 59 display very similar reactivities.

  DOI：

  10.1039/p19930002395

文献信息

• Intramolecular Diels–Alder reactions of vinylfurans leading to furanodecalins
  作者：Philip Cornwall、Colin P. Dell、David W. Knight

  DOI：10.1039/p19930002395

  日期：——

  Thermolysis of the (2E,8Z)-9-(2-furyl)nonadienoate 25 at 290-degrees-C leads to an essentially quantitative yield of a single furanodecalin 26, whereas the corresponding (2E,8E)-isomer 34 undergoes a non-stereoselective cyclisation leading to the furanodecalins 26 and 35. (Z)-Alkenoate functions undergo partial isomerisation prior to cyclisation and so lead to mixtures of isomers. Alkyl groups can be incorporated around the reaction sites, but this can result in overwhelming competition from side reactions. The corresponding 3-furyl analogues 56 and 59 display very similar reactivities.