(Z)-2-chloro-3-(4-methoxyphenyl)acrylic acid methyl ester | 71481-00-0

• 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)-2-chloro-3-(4-methoxyphenyl)acrylic acid methyl ester
• 英文别名: methyl 2-chloro-3-(4-methoxyphenyl)prop-2(Z)-enoate；(Z)-methyl 3-(4-methoxyphenyl)-2-chloropropenoate；methyl (Z)-2-chloro-3-(4-methoxyphenyl)propenoate；(Z)-methyl 2-chloro-3-(4-methoxyphenyl)acrylate；methyl 2-chloro-3-(4-methoxyphenyl)acrylate；z-Methyl-2-chloro-3-(4'-methoxyphenyl)propenoate；methyl (Z)-2-chloro-3-(4-methoxyphenyl)prop-2-enoate
• CAS: 71481-00-0；119555-96-3
• 化学式: C₁₁H₁₁ClO₃
• 分子量: 226.66
• InChiKey: BTZYLNJRVBBKNQ-YFHOEESVSA-N

物化性质

• 熔点：
  58.8-59.8 °C
• 沸点：
  339.9±27.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-2-chloro-3-(4-methoxyphenyl)acrylic acid methyl ester 在 氨 作用下， 反应 17.0h， 以43%的产率得到trans-2-(4-methoxyphenyl)aziridine-3-carboxylic acid amide
  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：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (Z)-2-chloro-3-(4-methoxyphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  Cabaleiro, Mercedes C.; Garay, Raul O., Journal of the Chemical Society. Perkin transactions II, 1986, p. 1091 - 1096

  摘要：

  DOI：

文献信息

• Titanium mediated olefination of aldehydes with α-haloacetates: an exceptionally stereoselective and general approach to (Z)-α-haloacrylates
  作者：John Kallikat Augustine、Agnes Bombrun、Srinivasa Venkatachaliah、Anandh Jothi

  DOI：10.1039/c3ob41592a

  日期：——

  An exceptionally stereoselective and general synthesis of (Z)-α-haloacrylates, ready to undergo various synthetic transformations, has been demonstrated from α-haloacetates and aldehydes in a one-pot manner via the titanium-enolate based asymmetric aldol condensation. Besides being an expedient synthetic procedure, the ready availability of diverse α-haloacetates, exceptional stereoselectivity, and high yields make the process a versatile transformation in organic synthesis. The potential of this method in up-scaling operations has been illustrated.

  展示了一种异常立体选择性和通用性合成（Z）-α-卤代丙烯酸酯的方法，该方法通过钛烯醇基催化的不对称 aldol 凝缩反应，采用 α-卤代乙酸酯和醛以一步法进行合成。这种合成方法不仅便捷，而且多样的 α-卤代乙酸酯的可得性、出色的立体选择性和高产率使得该过程在有机合成中具有多功能性。该方法在放大操作中的潜力也得到了展示。
• 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。
• Biocatalyzed Enantioselective Reduction of Activated C=C Bonds: Synthesis of Enantiomerically Enriched α-Halo-β-arylpropionic Acids
  作者：Elisabetta Brenna、Francesco G. Gatti、Alessia Manfredi、Daniela Monti、Fabio Parmeggiani

  DOI：10.1002/ejoc.201100537

  日期：2011.7

  The enantioselective biocatalyzed reduction of the C=C bond of some (Z)-methyl α-halo-β-arylacrylates was investigated. The reaction was performed by baker's yeast fermentation and Old Yellow Enzymes 1–3 mediated biotransformations. The final products were, respectively, enantiomerically enriched (S)-α-halo-β-arylpropionic acids and their methyl esters, and ester hydrolysis was promoted in the whole

  研究了对映选择性生物催化还原一些 (Z)-α-卤代-β-芳基丙烯酸酯的 C=C 键。该反应通过面包酵母发酵和老黄酶 1-3 介导的生物转化进行。最终产物分别是富含对映异构体的 (S)-α-卤代-β-芳基丙酸及其甲酯，并且在整个细胞系统中促进了酯水解。当芳环被吸电子基团取代时，观察到高转化率和对映选择性值。进一步处理这些富含对映体的 (S)-卤酸中的两种，得到对位取代的 D-苯丙氨酸。
• Synthesis of dihalohydrins and tri- and tetra-substituted olefins
  申请人：Board of Regents, The University of Texas System

  公开号：US20040143125A1

  公开（公告）日：2004-07-22

  A novel synthesis reaction for highly stereospecific tri- and tetra-substituted olefins is described. A single stereoisomer of stable &agr;-halo-&agr;,&bgr;-ester is produced in high yield by the reaction of aldehyde or ketone with a trihalogenated compound such as trichloroacetate in the presence of CrCl 2 in a solvent. By varying the amount of CrCl 2 used, the stable dihalohydrin intermediate may be obtained as well.

  描述了一种用于高度立体特异性三取代和四取代烯烃的新合成反应。通过醛或酮与三卤代化合物（如三氯乙酸盐）在溶剂中在CrCl2存在下的反应，可以高产率地产生稳定的α-卤代-α，β-酯的单立体异构体。通过改变使用的CrCl2量，也可以获得稳定的二卤水合物中间体。