(2E,8E)-9-(2-methyl-5-oxo-2H-furan-4-yl)nona-2,8-dienal | 207864-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (2E,8E)-9-(2-methyl-5-oxo-2H-furan-4-yl)nona-2,8-dienal
• CAS: 207864-47-9
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: AAQVQWFBWSNRGM-CDJQDVQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,8E)-9-(2-methyl-5-oxo-2H-furan-4-yl)nona-2,8-dienal 在 ditertiary butylcresol 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以25%的产率得到(3S,3aR,4S,4aR,8aS)-3-Methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,8a-decahydro-naphtho[2,3-c]furan-4-carbaldehyde
  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：

  6-溴正己醇 在 喹啉 、 正丁基锂 、 草酰氯 、 Pd(BaSO₄) 、 氢氟酸 、 氢气 、 草酸 、 三乙胺 、 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 104.0h， 生成 (2E,8E)-9-(2-methyl-5-oxo-2H-furan-4-yl)nona-2,8-dienal
  参考文献：
  名称：

  针对（±）-半胱氨酸的全合成的研究

  摘要：

  根据三烯10的分子内Diels-Alder反应报道了醛11a的合成，三烯10的丁烯内酯-二烯部分是通过将（Z）-烯酸酯5的烯醇与2的缩合反应一步获得的。乙酰氧基丙醛。醛11a具有重要的毒蕈碱受体拮抗剂喜巴因的三环部分的正确立体化学。

  DOI：

  10.1016/0040-4039(95)01520-5

文献信息

• Studies directed towards the total synthesis of (±)-himbacine
  作者：Govert De Baecke、Pierre J. De Clercq

  DOI：10.1016/0040-4039(95)01520-5

  日期：1995.10

  The synthesis of aldehyde 11a is reported based upon the intramolecular Diels-Alder reaction of triene 10, the butenolide-diene part of which was obtained in one step via the condensation of the enolate derived from the (Z)-enoate ester 5 with 2-acetoxypropanal. Aldehyde 11a possesses the correct stereochemistry of the tricyclic part of himbacine, an important muscarine receptor antagonist.

  根据三烯10的分子内Diels-Alder反应报道了醛11a的合成，三烯10的丁烯内酯-二烯部分是通过将（Z）-烯酸酯5的烯醇与2的缩合反应一步获得的。乙酰氧基丙醛。醛11a具有重要的毒蕈碱受体拮抗剂喜巴因的三环部分的正确立体化学。
• Studies Directed Towards the Total Synthesis of (+)-Himbacine
  作者：Sven Hofman

  DOI：10.1055/s-1998-5928

  日期：1998.3

  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.