methyl (Z)-2-chloro-3-(4-chlorophenyl)propenoate

• 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: methyl (Z)-2-chloro-3-(4-chlorophenyl)propenoate
• 英文别名: (Z)-methyl 3-(4-chlorophenyl)-2-chloropropenoate；methyl 2-chloro-3-(4-chlorophenyl)acrylate；z-Methyl-2-chloro-3-(4'-chlorophenyl)propenoate；methyl (Z)-2-chloro-3-(4-chlorophenyl)prop-2-enoate
• 化学式: C₁₀H₈Cl₂O₂
• 分子量: 231.078
• InChiKey: CRCSNGHNPLXFMK-TWGQIWQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  methyl (Z)-2-chloro-3-(4-chlorophenyl)propenoate 在 氨 作用下， 反应 24.0h， 以84%的产率得到(2R,3R)-3-(4-chlorophenyl)aziridine-2-carboxamide
  参考文献：
  名称：

  Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols

  摘要：

  Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-alpha-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides. The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.

  DOI：

  10.1021/jo00010a027
• 作为产物：
  描述：

  1-(4-chlorophenyl)-2,3,3-trichloro-1-oxopropene 在 sodium tetrahydroborate 、 硫酸 、 水 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 methyl (Z)-2-chloro-3-(4-chlorophenyl)propenoate
  参考文献：
  名称：

  Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols

  摘要：

  Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-alpha-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides. The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.

  DOI：

  10.1021/jo00010a027

文献信息

• Reactions of α,β-Unsaturated Carboxylates, Malonates and Phenylacetates with Manganese(III) Acetate in the Presence of Chloride Ions
  作者：Hiroshi Yonemura、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1246/bcsj.60.809

  日期：1987.2

  The reaction of alkyl (E)-3-phenylpropenoates with manganese(III) acetate in the presence of Cl− ions gave alkyl (Z)-2-chloro-3-phenylpropenoates and alkyl 2,3-dichloro-3-phenylpropanoates. Ethyl (E)-2,3-diphenylpropenoate yielded ethyl 2,3-dichloro-2,3-diphenylpropanoate. Alkyl 3,3-diphenylpropenoates gave mainly alkyl 2-chloro-3,3-diphenyl-propenoates. Ethyl 1-cyclohexenecarboxylate gave ethyl 1

  (E)-3-苯基丙烯酸烷基酯与乙酸锰(III)在Cl-离子存在下的反应产生(Z)-2-氯-3-苯基丙烯酸烷基酯和2,3-二氯-3-苯基丙酸烷基酯。(E)-2,3-二苯基丙烯酸乙酯产生2,3-二氯-2,3-二苯基丙酸乙酯。3,3-二苯基丙烯酸烷基酯主要产生2-氯-3,3-二苯基-丙烯酸烷基酯。1-环己烯羧酸乙酯得到1,2-二氯环己烷羧酸乙酯。丙二酸二甲酯产生二氯丙二酸二甲酯和1,2-二氯-1,1,2,2-乙四甲酸四甲酯。取代的丙二酸酯产生α-氯衍生物。苯乙酸甲酯生成α-乙酰氧基衍生物。
• Ru-catalyzed highly chemo- and enantioselective hydrogenation of γ-halo-γ,δ-unsaturated-β-keto esters under neutral conditions
  作者：Xin Ma、Wanfang Li、Xiaoming Li、Xiaoming Tao、Weizheng Fan、Xiaomin Xie、Tahar Ayad、Virginie Ratovelomanana-Vidal、Zhaoguo Zhang

  DOI：10.1039/c2cc30925d

  日期：——

  Finely-tuned ruthenium-catalyzed highly chemoselective and enantioselective hydrogenation of gamma-halo-gamma,delta-unsaturated-beta-keto esters at the carbonyl group was achieved under neutral reaction conditions (ee up to 97%). Both olefin and alkenyl halogen moieties, which are labile under hydrogenation conditions, remained untouched during the reaction.

  在中性反应条件下（ee高达97％），实现了钌的精细调节，催化了羰基上的gamma-卤代-gamma，δ-不饱和β-酮酸酯的高度化学选择性和对映选择性氢化。在氢化条件下不稳定的烯烃和烯基卤素部分都在反应过程中保持不变。
• Process for the preparation of .alpha.-halocinnamate esters
  申请人：The Dow Chemical Company

  公开号：US04727181A1

  公开（公告）日：1988-02-23

  Prepare esters of .alpha.-halocinnamic acid and related compounds in high yield under relatively mild conditions.

  在相对温和的条件下高产地制备.alpha.-卤代肉桂酸及相关化合物的酯。
• Cabaleiro, Mercedes C.; Garay, Raul O., Journal of the Chemical Society. Perkin transactions II, 1986, p. 1091 - 1096
  作者：Cabaleiro, Mercedes C.、Garay, Raul O.

  DOI：——

  日期：——
• YONEMURA HIROSHI; NISHINO HIROSHI; KUROSAWA KAZU, BULL. CHEM. SOC. JAP., 60,(1987) N 2, 809-811
  作者：YONEMURA HIROSHI、 NISHINO HIROSHI、 KUROSAWA KAZU

  DOI：——

  日期：——