(E)-2-(3,4-Dimethyl-2-oxo-3-cyclopenten-1-ylidene)acetic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-2-(3,4-Dimethyl-2-oxo-3-cyclopenten-1-ylidene)acetic acid ethyl ester
• 英文别名: ethyl (2E)-2-(3,4-dimethyl-2-oxocyclopent-3-en-1-ylidene)acetate
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: BOXMVKRVGAJRDG-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  2,3-二甲基丁-2-烯醛 在 manganese(IV) oxide 、 1,2-环氧辛烷 、 lithium diisopropyl amide 、 天然维生素E 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 30.25h， 生成 (E)-2-(3,4-Dimethyl-2-oxo-3-cyclopenten-1-ylidene)acetic acid ethyl ester
  参考文献：
  名称：

  Enynones in Organic Synthesis. 7. Substituent Effects on the .alpha.-Tocopherol-Catalyzed Cyclization of Enynones to Methylenecyclopentenones. Convenient Syntheses of Members of the Methylenomycin Class of Antibiotics

  摘要：

  Substituent effects on the a-tocopherol (vitamin E, 3b) catalyzed cyclization of a wide variety of enynones 1a-z to methylenecyclopentenones 7a-z have been examined, with particular emphasis given to electron-withdrawing and -donating groups at positions 2-4 and 6. In general, electron-withdrawing groups at positions 4 and 6 dramatically accelerate the cyclization process, while strong electron-donating groups at positions 3 and 4 completely inhibit reaction. Relatively little effect is exerted by groups at C-2, except for the methyl ester derivative 1i, which is totally unreactive. This methodology was employed in the syntheses of the methylenecyclopentenone antibiotics methylenomycin B (7a) and desepoxy-4,5-didehydromethylenomycin A (7z) and in formal syntheses of methylenomycin A (8) and xanthocidin (9).

  DOI：

  10.1021/jo00097a036

文献信息

• Pauson-Khand reaction with allenic compounds II: Reactivity of functionalized allenes
  作者：Mohammed Ahmar、Olivier Chabanis、Jerôme Gauthier、Bernard Cazes

  DOI：10.1016/s0040-4039(97)01151-9

  日期：1997.7

  The cobalt-mediated cycloaddition of alkynes with functionalized allenes were shown to lead to different 4- and 5-alkylidenecyclopent-2-enones 4–6. Regioselectivity depends on both steric and electronic effects of the substituents.

  炔与功能化的烯键的钴介导的环加成反应可导致产生不同的4-和5-亚烷基环戊-2-烯酮4-6。区域选择性取决于取代基的空间和电子效应。