2-Chlor-zimtsaeure-ethylester | 26880-33-1

• 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: 2-Chlor-zimtsaeure-ethylester
• 英文别名: Ethyl 2-chloro-3-phenylprop-2-enoate；ethyl 2-chloro-3-phenylprop-2-enoate
• CAS: 26880-33-1
• 化学式: C₁₁H₁₁ClO₂
• 分子量: 210.66
• InChiKey: YMMZTPSQWDXUGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Chlor-zimtsaeure-ethylester 在 肼 作用下， 生成 5-苯基-1H-吡唑-3-醇
  参考文献：
  名称：

  Reactions of Ethyl Diazoacetate with Aromatic Compounds Containing Hetero Atoms Attached to the Benzyl Carbon

  摘要：

  DOI：

  10.1021/ja01637a064
• 作为产物：
  描述：

  ethyl 2,3-dichloro-3-phenylpropanoate 在 三乙胺 作用下， 以 苯 为溶剂， 以73%的产率得到2-Chlor-zimtsaeure-ethylester
  参考文献：
  名称：

  Samarenko, V. Ya.; Markova, N. R.; Passet, B. V., Journal of Organic Chemistry USSR (English Translation), 1982, p. 122 - 127

  摘要：

  DOI：

文献信息

• New Synthetic Approach to α-Chlorocinnamates: First Example of Synthesis of Functionally Substituted Alkenes Using Catalytic Olefination Reaction
  作者：Valentine G. Nenajdenko、Olesya N. Lenkova、Alexey V. Shastin、Elizabeth S. Balenkova

  DOI：10.1055/s-2004-815951

  日期：——

  A new simple and efficient transformation of carbonyl compounds to α-chlorocinnamates is described. Catalytic olefination reaction with ethyl trichloroacetate gives target alkenes in moderate to good yields. The reaction with aromatic aldehydes proceeds stereoselectively to form preferably Z-isomers.

  描述了一种将羰基化合物简单有效地转化为 α-氯肉桂酸酯的新方法。与三氯乙酸乙酯的催化烯化反应以中等至良好的收率得到目标烯烃。与芳族醛的反应立体选择性地进行以形成优选的Z-异构体。
• A convenient method for the synthesis of (Z)-α-haloacrylates: Lewis base-catalyzed carbonyl olefination using α-halo-C,O-bis(trimethylsilyl)ketene acetals
  作者：Makoto Michida、Takako Toriumi、Teruaki Mukaiyama

  DOI：10.1016/j.tetlet.2009.02.019

  日期：2009.7

  synthesis of (Z)-α-haloacrylates from various aldehydes that uses α-halogenated ethyl-C,O-bis(trimethylsilyl)ketene acetals in the presence of a Lewis base catalyst such as acetate salts was established. This procedure gives the corresponding α-halo-α,β-unsaturated esters in high yields with excellent stereoselectivity from E/Z mixtures of ketene silyl acetals under mild conditions.

  建立了一种非常有用的方法，用于在路易斯碱催化剂（如乙酸盐）存在下，使用α-卤代乙基-C，O-双（三甲基甲硅烷基）乙烯醇缩醛，从各种醛类中立体选择性合成（Z）-α-卤代丙烯酸酯。 。该方法在温和的条件下从乙烯酮甲硅烷基乙缩醛的E / Z混合物中以高立体异构选择性高收率地得到了相应的α-卤代-α，β-不饱和酯。
• Microwave-Assisted Tandem Nucleophilic Substitution-Wittig Reaction of α<i>-</i>Hypervalent Iodine Functionalized Phosphonium Ylide
  作者：Xian Huang、Xiaochun Yu

  DOI：10.1055/s-2002-34893

  日期：——

  Under microwave irradiation conditions the tandem nucleophilic substitution-Wittig reaction of α-hypervalent iodine functionalized phosphonium ylide can occur readily to afford α-heteroatom substituted-α,β-unsaturated enoates in good yields stereoselectively.

  在微波辐照条件下，δ-高价碘官能化膦酰亚胺很容易发生串联亲核取代-维蒂希反应，从而以良好的收率立体选择性地获得δ-杂原子取代的δ,δ-不饱和烯酸盐。
• A Novel and Convenient Protocol for Synthesis of α-Haloacrylates
  作者：Biao Jiang、Ying Dou、Xiangya Xu、Min Xu

  DOI：10.1021/ol702859y

  日期：2008.2.1

  A.novel and convenient protocol for synthesis of alpha-haloacrylates starting from phosphonium ylide and aldedyde or alcohol was described. Halodimethylsulfonium halide was used for the first time in halogenation of phosphonium ylide. Good yield as well as a high Z/E ratio were shown in representative cases, and an umpolung dimethyl sulfide-ylide species might be involved as an intermediate.
• Claisen, Chemische Berichte, 1905, vol. 38, p. 706
  作者：Claisen

  DOI：——

  日期：——