2-乙氧基-3-甲基丁-2-烯醛 | 89005-36-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙氧基-3-甲基丁-2-烯醛
• 英文名称: 2-Ethoxy-3-methyl-but-2-enal
• 英文别名: 2-Ethoxy-3-methylbut-2-enal
• CAS: 89005-36-7
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: BLQPHJHXSPUSGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙氧基-3-甲基丁-2-烯醛 在 manganese(IV) oxide 、 正丁基锂 、 三苯基甲烷 、 1,2-环氧辛烷 、 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 37.25h， 生成 (E)-2-Ethoxy-3-methyl-5-ethylidene-2-cyclopenten-1-one
  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
• 作为产物：
  描述：

  {[1-(Benzenesulfinyl)-3-methylbuta-1,2-dien-1-yl]sulfanyl}benzene 在 mercury dichloride 作用下， 以 水 、 乙腈 为溶剂， 生成 2-乙氧基-3-甲基丁-2-烯醛
  参考文献：
  名称：

  亚丙基亚砜的化学：炔醇的新转化

  摘要：

  描述了由1-苯硫基取代的炔醇衍生的丙二烯的制备和反应。这种化学方法提供了新的路线，以开发出烯丙基硫醚，酰基阴离子当量和取代的不饱和醛。

  DOI：

  10.1039/c39830001209

文献信息

• CUTTING, I.;PARSONS, P. J., J. CHEM. SOC. CHEM. COMMUN., 1983, 21, 1209-1210
  作者：CUTTING, I.、PARSONS, P. J.

  DOI：——

  日期：——
• Chemistry of allene sulphoxides: novel transformations of acetylenic alcohols
  作者：Ian Cutting、Philip J. Parsons

  DOI：10.1039/c39830001209

  日期：——

  The preparation and reactions of allenes derived from 1-phenylthio substituted acetylenic alcohols are described; this chemistry offers new routes to allenyl sulphides, acyl anion equivalents, and substituted unsaturated aldehydes.

  描述了由1-苯硫基取代的炔醇衍生的丙二烯的制备和反应。这种化学方法提供了新的路线，以开发出烯丙基硫醚，酰基阴离子当量和取代的不饱和醛。
• 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
  作者：Peter A. Jacobi、Harry L. Brielmann、Reginald O. Cann

  DOI：10.1021/jo00097a036

  日期：1994.9

  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).