(Z)-ethyl 2-chloro-3-(4-nitrophenyl)-2-propenoate | 91349-22-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-ethyl 2-chloro-3-(4-nitrophenyl)-2-propenoate
• 英文别名: ethyl (Z)-2-chloro-3-(4-nitrophenyl)acrylate；α-chloro-4-nitro-trans-cinnamic acid ethyl ester；α-Chlor-4-nitro-trans-zimtsaeure-aethylester；ethyl α-chloro-4-nitrocinnamate；2-Chloro-3-(4-nitro-phenyl)-acrylic acid ethyl ester；ethyl (Z)-2-chloro-3-(4-nitrophenyl)prop-2-enoate
• CAS: 91349-22-3
• 化学式: C₁₁H₁₀ClNO₄
• 分子量: 255.658
• InChiKey: YCKVXWSYKJLYRV-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 (Z)-ethyl 2-chloro-3-(4-nitrophenyl)-2-propenoate
  参考文献：
  名称：

  Pfeiffer, Chemische Berichte, 1914, vol. 47, p. 1768

  摘要：

  DOI：

文献信息

• Ir(ppy)₃-Catalyzed, Visible-Light-Mediated Reaction of α-Chloro Cinnamates with Enol Acetates: An Apparent Halogen Paradox
  作者：Thomas Föll、Julia Rehbein、Oliver Reiser

  DOI：10.1021/acs.orglett.8b02484

  日期：2018.9.21

  activation of vinyl chlorides derived from α-chloro ethyl cinnamates via oxidative quenching of excited photocatalyst fac-Ir(ppy)3 is described. Upon photoelectron transfer and chloride extrusion, the corresponding vinyl radical can be efficiently trapped by enol acetates, giving rise to synthetically useful 1,4-dicarbonyl compounds in good to excellent yields. This transformation is distinguished by

  描述了由α-氯乙基肉桂酸酯衍生的氯乙烯的可见光介导的活化，该活化是通过激发光催化剂fac -Ir（ppy）3的氧化猝灭。在光电子转移和氯化物挤出时，相应的乙烯基可以被烯醇乙酸酯有效地捕集，从而以良好的至优异的产率产生了合成上有用的1，4-二羰基化合物。这种转化的特征是温和且对环境无害的反应条件，并且可以在数克范围内进行，这与对比的α-溴乙基肉桂酸酯形成鲜明对比，后者在各种条件下均显示出低转化率。
• A convenient synthesis of olefins via deacylation reaction
  作者：Shogo Nakatsu、Aider T Gubaidullin、Vakhid A Mamedov、Sadao Tsuboi

  DOI：10.1016/j.tet.2004.01.022

  日期：2004.3

  A convenient and environmentally-friendly synthetic method of olefins via deacylation reaction is described. The reaction gives olefins by condensation of aldehydes with a variety of 1,3-dicarbonyl compounds in the presence of anhydrous potassium carbonate at room temperature in high yields (70–90%) in one step. The synthetic potential of this strategy can be used as an alternative procedure to the

  描述了一种通过脱酰基反应的方便且环境友好的烯烃合成方法。在无水碳酸钾存在下，室温下一步反应将醛与各种1,3-二羰基化合物缩合反应，可制得烯烃。该策略的综合潜力可作为Wittig，Wittig-Horner反应的替代方法。通过正确的射频和X射线分析的NOE实验确定了所得烯烃的立体化学。脱酰反应的E / Z选择性取决于1，3-二羰基化合物的α-取代基。
• Stabilized haloylides: synthesis and reactivity
  作者：Margaret M. Kayser、Jun Zhu、Donald L. Hooper

  DOI：10.1139/v97-157

  日期：1997.10.1

  This paper describes simple and successful methods for the preparation of stabilized halogenated phosphoylides and discusses their stability, reactivity, and utility in organic synthesis. Preparations of several halogenated compounds including pharmaceutically interesting enol lactones are reported. Keywords: halogenated stabilized ylides, preparation, structure, stability, reactivity, applications; vinylic halides, halo enol lactones.

  本文描述了制备稳定卤代膦酰亚胺的简单而成功的方法，并讨论了它们在有机合成中的稳定性、反应性和实用性。报道了几种卤代化合物的制备，包括具有药学兴趣的烯基烯醇内酯。 关键词：卤代稳定亚胺，制备，结构，稳定性，反应性，应用；烯基卤代化合物，卤代烯醇内酯。
• Chemo-and stereoselectivity of the reaction of aromatic aldehydes with triphenylphosphine and trichloroacetic acid derivatives
  作者：E. D. Matveeva、A. S. Erin、A. G. Osetrov、I. F. Leshcheva、A. L. Kurts

  DOI：10.1134/s1070428006030080

  日期：2006.3

  Aromatic aldehydes react with triphenylphosphine and ethyl trichloroacetate or trichloroacetonitrile to give the corresponding benzylidene dichlorides or alpha-chlorocinnamic acid derivatives. The chemo- and regioselectivity of these reactions depend on both the substituent in the aromatic ring and reaction conditions. The product configuration was determined on the basis of the coupling constans (2)J(CH) and (3)J(CH) in the C-13 NMR spectra.
• Efficient Electrosynthesis of α-Chloro-α,β-Unsaturated Carboxylic and Phosphonic Esters Using Magnesium Electrochemical Activation
  作者：Sophie Goumain

  DOI：10.1055/s-1999-3501

  日期：1999.6