(E/Z)-2-Cyano-3,5-dimethyl-2-hexenoic acid ethyl ester | 759-53-5

• 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: (E/Z)-2-Cyano-3,5-dimethyl-2-hexenoic acid ethyl ester
• 英文别名: 3,5-Dimethyl-2-cyan-hexen-2-saeure-1-ethylester；(1-Methyl-isopentyliden)-cyanessigsaeure-ethylester；α-Cyan-β-methyl-γ-isopropyl-crotonsaeureethylester；2-Cyan-3,5-dimethyl-hex-2-ensaeure-ethylester；2.4-Dimethyl-penten-(1)-dicarbonsaeure-(1.1)-aethylester-nitril；(1.3-Dimethyl-butyliden)-malonsaeure-aethylester-nitril；(1.3-Dimethyl-butyliden)-cyanessigsaeure-aethylester；2-cyano-3,5-dimethyl-hex-2-enoic acid ethyl ester；2-Cyan-3,5-dimethyl-hex-2-ensaeure-aethylester；Ethyl 2-cyano-3,5-dimethylhex-2-enoate
• CAS: 759-53-5
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: NHEROOPJNHZIMY-UHFFFAOYSA-N

物化性质

• 沸点：
  130-133 °C(Press: 12 Torr)
• 密度：
  0.9684 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.636
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  溴丁基-镁 、 (E/Z)-2-Cyano-3,5-dimethyl-2-hexenoic acid ethyl ester 在 copper(l) iodide 作用下， 以 乙醚 为溶剂， 生成 3-Methyl-3-isobutyl-2-cyan-oenanthsaeure-ethylester
  参考文献：
  名称：

  Desgrandchamps,G. et al., Bulletin de la Societe Chimique de France, 1961, p. 264 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基-2-戊酮 、 氰乙酸乙酯 在 乙酸铵 、 溶剂黄146 、 苯 作用下， 生成 (E/Z)-2-Cyano-3,5-dimethyl-2-hexenoic acid ethyl ester
  参考文献：
  名称：

  Cope et al., Journal of the American Chemical Society, 1941, vol. 63, p. 3455

  摘要：

  DOI：

文献信息

• Steric effects in high pressure Knoevenagel reactions
  作者：Gérard Jenner

  DOI：10.1016/s0040-4039(00)01930-4

  日期：2001.1

  The pressure effect in Knoevenagel condensations involving ketones and ethyl cyanoacetate is studied. The reactions are diversely affected. For cyclic ketones there is a small effect on the reaction yield. However, in the case of acyclic ketones, the sensitivity of the reaction to pressure increases with increasing steric congestion of the ketone. Such a result highlights the synthetic utility of high pressure for the preparation of hindered functionalized alkenes. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Cope; Hofmann; Hardy, Journal of the American Chemical Society, 1941, vol. 63, p. 1855
  作者：Cope、Hofmann、Hardy

  DOI：——

  日期：——
• Cope; Hancock, Journal of the American Chemical Society, 1938, vol. 60, p. 2904,2905
  作者：Cope、Hancock

  DOI：——

  日期：——
• Daviaud,G. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1971, vol. 272, p. 969 - 972
  作者：Daviaud,G. et al.

  DOI：——

  日期：——
• Synthesis of 4-isobutyl substituted thiophenes byGewald reaction
  作者：M. G�tschow、H. Schr�ter、G. Kuhnle、K. Eger

  DOI：10.1007/bf00813795

  日期：1996.3

  The Gewald reaction of 4-methyl-2-pentanone with alkyl cyanoacetates was investigated Alkyl 2-amino-4-isobutylthiophene-3-carboxylates (4) were formed, together with bis-(2-amino-3-alkoxycarbonyl-4-isobutyl-5-thienyl)-disulfides (5) and alkyl 2-amino-4-isobutyl-5-morpholinothiophene-3-carboxylates (6). The absence of any 4-methyl substituted aminothiophene in the product mixtures came up highly unexpected. The mechanism of the reaction is discussed with respect to previously reported suggestions.