(2E,8E)-9-(5-Methyl-2-oxo-2,5-dihydro-furan-3-yl)-nona-2,8-dienoic acid ethyl ester | 207864-46-8

• 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,8E)-9-(5-Methyl-2-oxo-2,5-dihydro-furan-3-yl)-nona-2,8-dienoic acid ethyl ester
• CAS: 207864-46-8
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: VXYPLZLNTVUPDM-GFULKKFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E,8E)-9-(5-Methyl-2-oxo-2,5-dihydro-furan-3-yl)-nona-2,8-dienoic acid ethyl ester 在 ditertiary butylcresol 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 (3R,3aS,4R,4aS,8aR)-3-Methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,8a-decahydro-naphtho[2,3-c]furan-4-carboxylic acid ethyl ester 、 (3R,3aS,4S,4aR,8aR)-3-Methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,8a-decahydro-naphtho[2,3-c]furan-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Studies Directed Towards the Total Synthesis of (+)-Himbacine

  摘要：

  A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.

  DOI：

  10.1055/s-1998-5928
• 作为产物：
  描述：

  4-[(E)-7-[tert-butyl(dimethyl)silyl]oxyhept-1-enyl]-2-methyl-2H-furan-5-one 在 草酰氯 、 氢氟酸 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 (2E,8E)-9-(5-Methyl-2-oxo-2,5-dihydro-furan-3-yl)-nona-2,8-dienoic acid ethyl ester
  参考文献：
  名称：

  Studies Directed Towards the Total Synthesis of (+)-Himbacine

  摘要：

  A convergent strategy towards himbacine (1), involving a Julia coupling between aldehyde 5 and sulfone 6 was found to be ineffective. The aldehyde 5 was synthesized via the thermal intramolecular cycloaddition of 4 with preferred formation of the endo-adduct. The Diels-Alder precursor 4 was obtained from butenolide 7, the result of a single-step condensation between the enoate derived from the (Z)-conjugated olefin 12 and 2-acetoxypropanal. In the context of the synthesis of sulfone 6 Taber's method for the synthesis of 2,6-trans-disubstituted piperidine was adapted towards a large scale synthesis of 49, a useful intermediate for the synthesis in this area.

  DOI：

  10.1055/s-1998-5928