cis-α-Chlor-zimtsaeure-methylester

• 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: cis-α-Chlor-zimtsaeure-methylester
• 英文别名: methyl (E)-2-chloro-3-phenylprop-2-enoate
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: OHXMZPBSQGEXEV-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 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

• 作为产物：
  描述：

  氯乙烯基苯 生成 cis-α-Chlor-zimtsaeure-methylester
  参考文献：
  名称：

  Schlosser,M.; Ladenberger,V., Chemische Berichte, 1967, vol. 100, p. 3893 - 3900

  摘要：

  DOI：

文献信息

• Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes
  作者：Roman Iakovenko、Jan Hlaváč

  DOI：10.1039/d0gc03081c

  日期：——

  Photoactivated metal free deuteration of a double bond was developed in an environmentally friendly manner.

  双键的光活化金属无氘化反应以环境友好的方式进行了开发。
• A Substrate-Driven Approach to Determine Reactivities of α,β-Unsaturated Carboxylic Esters Towards Asymmetric Bioreduction
  作者：Gábor Tasnádi、Christoph K. Winkler、Dorina Clay、Nargis Sultana、Walter M. F. Fabian、Mélanie Hall、Klaus Ditrich、Kurt Faber

  DOI：10.1002/chem.201200990

  日期：2012.8.13

  The degree of CC bond activation in the asymmetric bioreduction of α,β‐unsaturated carboxylic esters by ene‐reductases was studied, and general recommendations to render these “borderline‐substrates” more reactive towards enzymatic reduction are proposed. The concept of “supported substrate activation” was developed. In general, an additional α‐halogenated substituent proved to be beneficial for enzymatic

  研究了烯还原酶对α，β-不饱和羧酸酯的不对称生物还原中CC键的活化程度，并提出了一般建议，以使这些“边界底物”对酶促还原反应更具活性。开发了“支持的底物活化”的概念。通常，另外一个α-卤代取代基被证明对酶活性有益，而β-烷基或β-芳基取代基对非卤代底物的反应性有害，而α-氰基几乎没有作用。发现酯官能度的醇部分对反应速率具有强烈影响。总体而言，活动取决于空间效果和电子效果。
• One-pot synthesis of (<i>E</i>)-α-chloro-α,β-unsaturated esters
  作者：Usama Karama

  DOI：10.3184/030823409x460678

  日期：2009.7

  Chlorination of a phosphonate anion derived in situ from methyl bis(2,2,2-trifluoroethoxy)phosphonoacetate 2 followed by the addition of aldehydes constitutes a stereoselective single flask procedure for the preparation of E-configured α-chloro-α,β-unsaturated esters.

  将双(2,2,2-三氟乙氧基)膦酰基乙酸甲酯 2 原位生成的膦酸阴离子氯化，然后加入醛类物质，构成了制备 E 型 α-氯-α,β-不饱和酯的立体选择性单瓶程序。
• 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。