2-cyano-3-methyl-hept-2-enoic acid ethyl ester | 759-55-7

• 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: 2-cyano-3-methyl-hept-2-enoic acid ethyl ester
• 英文别名: 2-Methyl-hexen-(1)-dicarbonsaeure-(1.1)-aethylester-nitril；(1-Methyl-pentyliden)-malonsaeure-aethylester-nitril；(1-Methyl-pentyliden)-cyanessigsaeure-aethylester；2-Cyan-3-methyl-hept-2-ensaeure-aethylester；2-Cyan-3-methyl-hept-2-ensaeure-ethylester；Ethyl 2-cyano-3-methylhept-2-enoate
• CAS: 759-55-7
• 化学式: C₁₁H₁₇NO₂
• 分子量: 195.261
• InChiKey: UZBZHBFLVIDABH-UHFFFAOYSA-N

物化性质

• 沸点：
  149-150 °C(Press: 19 Torr)
• 密度：
  0.9709 g/cm3(Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  2-cyano-3-methyl-hept-2-enoic acid ethyl ester 在 乙醇 、 sodium ethanolate 作用下， 生成 2-cyano-2,3-dimethyl-hept-3-enoic acid ethyl ester
  参考文献：
  名称：

  Cope; Hancock, Journal of the American Chemical Society, 1938, vol. 60, p. 2904,2905

  摘要：

  DOI：
• 作为产物：
  描述：

  2-己酮 、 氰乙酸乙酯 在 哌啶 作用下， 23.0 ℃ 、300.0 MPa 条件下， 反应 2.0h， 以66%的产率得到2-cyano-3-methyl-hept-2-enoic acid ethyl ester
  参考文献：
  名称：

  Steric effects in high pressure Knoevenagel reactions

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)01930-4

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

  DOI：——

  日期：——
• Shevchenko,V.I. et al., Journal of general chemistry of the USSR, 1969, vol. 39, p. 2152 - 2156
  作者：Shevchenko,V.I. et al.

  DOI：——

  日期：——
• Energy Efficiency in Chemical Reactions:  A Comparative Study of Different Reaction Techniques
  作者：Mark J. Gronnow、Robin J. White、James H. Clark、Duncan J. Macquarrie

  DOI：10.1021/op0498060

  日期：2005.7.1

  Metrics for chemists are much argued, but the energy usage of a reaction has to be one of the most simple and effective methods of comparing technologies. In this concept paper, the energy consumed in preparing one mole of a chemical compound is compared for a variety of technologies. Data are gathered for traditional oil bath, supercritical CO2 (SC-CO2), and microwave reactors. Two different Suzuki couplings, a Knoevenagel condensation, and a Friedel-Crafts acylation are all compared in both the microwave and oil bath, as this is where the most noticeable differences were observed. The most notable result was an 85-fold reduction in energy demand on switching from oil bath to microwave reactor for a Suzuki reaction.
• Cope; Hancock, Journal of the American Chemical Society, 1938, vol. 60, p. 2904,2905
  作者：Cope、Hancock

  DOI：——

  日期：——