methyl 2-ethylidene-5-oxohexanoate

• 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 2-ethylidene-5-oxohexanoate
• 英文别名: methyl (2E)-2-ethylidene-5-oxohexanoate
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: OZIMMFCDUSRYDV-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲氧基乙酰-2-亚甲基丁酸 、 乙酰丙酮 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以91%的产率得到methyl 2-ethylidene-5-oxohexanoate
  参考文献：
  名称：

  Substitution of Allylic Functional Acetates: Stereoselective Synthesis of 2-Alkylidene-1,5-ketoesters

  摘要：

  Direct reaction of allylic functional acetates 1 and beta-diketones 3 in the presence of anhydrous potassium carbonate i n boiling absolute ethanol gave 2-alkylidene-1,5-ketoesters 4 in good to fair yields.

  DOI：

  10.1080/00397919408010208

文献信息

• Stereoselective Synthesis of (±)-Cephanolide B
  作者：Anding Li、Ziru He、Bingyan Liu、Zhen Yang、Zichun Zhang

  DOI：10.1021/acs.orglett.1c03579

  日期：2021.12.3

  A concise and stereoselective total synthesis of (±)-cephanolide B was achieved in 15 steps. The key steps in the synthesis were as follows: (i) an intermolecular Diels–Alder reaction followed by lactonization to form the oxabicyclo[2.2.2]octane DE ring; (ii) a tandem reaction, featuring an intramolecular Pauson–Khand reaction, a 6π-electrocyclization, and an oxidative aromatization by O2, to construct

  (±)-cephanolide B 的简洁和立体选择性全合成通过 15 个步骤实现。合成的关键步骤如下：（i）分子间 Diels-Alder 反应，然后内酯化形成氧杂双环[2.2.2]辛烷 DE 环；(ii) 以分子内 Pauson-Khand 反应、6π-电环化和 O 2的氧化芳构化为特征的串联反应，以构建 ABC-三环 (6-5-6)；(iii) 邻苯二甲酰过氧化物介导的芳烃氧化以安装 C-13 苯酚基团。
• Evans, Elizabeth H.; Hewson, Alan T.; March, Lorraine A., Journal of the Chemical Society. Perkin transactions I, 1987, p. 137 - 150
  作者：Evans, Elizabeth H.、Hewson, Alan T.、March, Lorraine A.、Nowell, Ian W.、Wadsworth, Alan H.

  DOI：——

  日期：——
• Synthesis of α-Alkylidene-δ-valerolactones via the Conjugate Addition of Ketone Enolates to Functionalized Allyl Acetates
  作者：P. Veeraraghavan Ramachandran、Annyt Bhattacharyya

  DOI：10.3987/com-09-s(s)109

  日期：——

  Sequential addition of ketone enolates to allyl acetates bearing an ester, followed by reduction and cyclization provides a variety of substituted alpha-alkylidene-delta-valerolactones.
• Beltaief I., Amri H., Synth. Commun, 24 (1994) N 14, S 2003-2010
  作者：Beltaief I., Amri H.

  DOI：——

  日期：——
• Substitution of Allylic Functional Acetates: Stereoselective Synthesis of 2-Alkylidene-1,5-ketoesters
  作者：I. Belta[icaron]ef、H. Amri

  DOI：10.1080/00397919408010208

  日期：1994.7

  Direct reaction of allylic functional acetates 1 and beta-diketones 3 in the presence of anhydrous potassium carbonate i n boiling absolute ethanol gave 2-alkylidene-1,5-ketoesters 4 in good to fair yields.