(Z)-3-(4-chloro-phenyl)-3-cyano-propenoic acid potassium salt

• 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)-3-(4-chloro-phenyl)-3-cyano-propenoic acid potassium salt
• 英文别名: potassium 3-(4-chlorophenyl)-3-cyanoacrylate；(Z)-3-(4-Chlorophenyl)-3-cyano-2-propenoic acid potassium salt；potassium;(Z)-3-(4-chlorophenyl)-3-cyanoprop-2-enoate
• 化学式: C₁₀H₅ClNO₂*K
• 分子量: 245.706
• InChiKey: CEOXEOVYKVKZGN-HAAWTFQLSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4-chloro-phenyl)-3-cyano-propenoic acid potassium salt 在 盐酸 、 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 R(+)-巴氯芬盐酸盐
  参考文献：
  名称：

  老黄色酶色氨酸116突变体介导的（Z）-β-芳基-β-氰基丙烯酸酯生物还原的对映选择性相反：（R）-和（S）-β-芳基-γ-内酰胺的合成方法

  摘要：

  老黄酶1的Trp 116突变体催化（Z）-β-芳基-β-氰基丙烯酸酯的还原反应，根据116位氨基酸的性质给出相反的对映选择性。底物以“经典”方向与酶的活性位点结合，提供还原产物的（S）-对映异构体。当氨基酸大小增加（例如亮氨酸）时，底物会采用“翻转”结合模式，该模式会转换为相应的（R）衍生物。对于大块氨基酸（例如，野生型色氨酸），不会发生还原反应。如此制备的对映体富集的氰基丙酸酯可转化为相应的（S）-和（R）-β-芳基-γ-内酰胺类化合物，通过顺序单锅法中的简单官能团互变，属于抑制性神经递质的前体，属于γ-氨基丁酸类。

  DOI：

  10.1002/adsc.201500206
• 作为产物：
  描述：

  乙醛酸 、 对氯苯乙腈 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (Z)-3-(4-chloro-phenyl)-3-cyano-propenoic acid potassium salt
  参考文献：
  名称：

  激发态光化学[2+4]-二聚反应

  摘要：

  芳基马来酰亚胺经历意想不到的[2+4]-光二聚化的新颖发散激发态反应性被提出，并具有详细的机制原理。形成的光二聚体的立体化学与在热条件下观察到的产物互补，并且由光激发反应物中普遍存在的非键相互作用的类型决定。

  DOI：

  10.1002/anie.202316662

文献信息

• A short, chemoenzymatic route to chiral β-aryl-γ-amino acids using reductases from anaerobic bacteria
  作者：Anna Fryszkowska、Karl Fisher、John M. Gardiner、Gill M. Stephens

  DOI：10.1039/b919526b

  日期：——

  A short chemoenzymatic synthesis of β-aryl-γ-aminobutyric acids has been developed, based on a highly enantioselective biocatalytic reduction of β-aryl-β-cyano-α,β-unsaturated carboxylic acids.

  基于 β-芳基-β-氰基-α,β-不饱和羧酸的高度对映选择性生物催化还原，开发了一种短化学酶促合成 β-芳基-γ-氨基丁酸。
• Asymmetric hydrogenation of maleic anhydrides catalyzed by Rh/bisphosphine-thiourea: efficient construction of chiral succinic anhydrides
  作者：Zhengyu Han、Rui Wang、Guoxian Gu、Xiu-Qin Dong、Xumu Zhang

  DOI：10.1039/c7cc01626c

  日期：——

  Asymmetric hydrogenation of various 3-substituted maleic anhydrides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) under mild conditions was successfully developed. A wide range of 3-alkyl and 3-aryl maleic anhydrides was hydrogenated well to...

  成功开发了Rh /双膦-硫脲（ZhaoPhos）在温和条件下催化的各种3-取代的马来酸酐的不对称加氢反应。广泛地将3-烷基和3-芳基马来酸酐进行氢化以制得...
• Fungicidal agents containing pyrrolidones as their active agents and use thereof for treating plants
  申请人：BASF Aktiengesellschaft

  公开号：US06586369B1

  公开（公告）日：2003-07-01

  Agrochemical compositions having fungicidal action and comprising as active compounds compounds of the formula I where R1 is hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl, formyl or C1-C6-haloalkylcarbonyl; R2 is halogen, C1-C6-alkylthio, C1-C6-alkoxy, C3-C6-cycloalkyl-C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyl, halo-C1-C6-alkoxy, C1-C6-alkylsulfonyl, C1-C6-alkylsulfinyl, halo-C1-C6-alkylsulfonyl, cyano or a radical NR13R14; R3-R12 are hydrogen, halogen, C1-C8-cycloalkyl, C1-C6-alkyl, halo-C1-C6-alkyl, C1-C6-alkoxy, halo-C1-C6-alkoxy, C1-C6-alkylsulfonyl, halo-C1-C6-alkylsulfonyl, formyl, C1-C6-alkylcarbonyl, cyano, C1-C6-alkylthio or phenyl, which may be unsubstituted or substituted by halogen, C1-C6-alkyl or halo-C1-C6-alkyl, R13 is hydrogen, C1-C6-alkyl, R14 is C1-C6-alkyl, C1-C8-cycloalkyl or, together with R13 and the nitrogen atom to which they are attached, a saturated or unsaturated heterocyclic five- or six-membered ring which contains one or two heteroatoms selected from the group consisting of nitrogen and oxygen, and their agriculturally useful salts are described.

  具有杀真菌作用的农药组合物，包括以下化合物作为活性化合物：式I中的化合物，其中R1为氢、C1-C6-烷基、C1-C6-烷基羰基、甲酰基或C1-C6-卤代烷基羰基；R2为卤素、C1-C6-烷基硫、C1-C6-烷氧基、C3-C6-环烷基-C1-C6-烷氧基、C1-C6-烷氧基-C1-C6-烷基、卤基-C1-C6-烷氧基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、卤基-C1-C6-烷基磺酰基、氰基或基团NR13R14；R3-R12为氢、卤素、C1-C8-环烷基、C1-C6-烷基、卤基-C1-C6-烷基、C1-C6-烷氧基、卤基-C1-C6-烷氧基、C1-C6-烷基磺酰基、卤基-C1-C6-烷基磺酰基、甲酰基、C1-C6-烷基羰基、氰基、C1-C6-烷基硫或苯基，可以是未取代或取代的卤素、C1-C6-烷基或卤基-C1-C6-烷基；R13为氢、C1-C6-烷基；R14为C1-C6-烷基、C1-C8-环烷基或与R13及其所连接的氮原子一起，形成饱和或不饱和的含有一或两个异原子的五元或六元杂环，所述异原子选自氮和氧的群，以及它们的农业有用盐。
• Design, Synthesis, and Evaluation of Metabolism-Based Analogues of Haloperidol Incapable of Forming MPP+-like Species
  作者：M. Lyles-Eggleston、R. Altundas、J. Xia、D. M. N. Sikazwe、P. Fan、Q. Yang、S. Li、W. Zhang、X. Zhu、A. W. Schmidt、M. Vanase-Frawley、A. Shrihkande、A. Villalobos、R. F. Borne、S. Y. Ablordeppey

  DOI：10.1021/jm0301033

  日期：2004.1.1

  The long-term, irreversible, Parkinsonism-like side effects of haloperidol have been speculated to involve several mechanisms. More recently, it has been speculated that the metabolic transformation to MPP+-like species may contribute to the Parkinsonism-like side effects. Because BCPP+ and its reduced analogue have been shown to possess the potential to destroy dopamine receptors in the nigrostriatum, we have designed new analogues of haloperidol lacking the structural features necessary to form neurotoxic quaternary species but retaining their dopamine-binding capacity. The most potent agent at the D2 receptor, the homopiperidine analogue 11, was found to be equipotent to haloperidol. It was also of interest to identify analogues with DA binding profiles similar to that of clozapine at the dopamine receptor subtypes. Evaluation of the proposed agents shows that the ratio of D2 to D4 (2) binding of clozapine was mimicked by 7 [K-i(D2) = 33, K-i(D3) = 200, K-i(D4) = 11 nM; K-i(D2)/K-i(D4) = 3] and 9 [K-i(D2) = 44, K-i(D3) = 170, K-i(D4) = 24 nM; K-i(D2)/K-i(D4) = 2]. A preliminary in-vivo testing of compound 7 shows that its behavioral profile is similar to that of clozapine. This profile suggests that there is a need for further evaluation of these two synthetic agents and their enantiomers for efficacy and lack of catalepsy in animal models.
• Condensation of arylacetonitriles with glyoxylic acid. Facile synthesis of arylmaleic acid derivatives
  作者：W. D. Dean、D. M. Blum

  DOI：10.1021/jo00079a044

  日期：1993.12