(Z)-3-(4-fluorophenyl)-2-hydroxyacrylic acid | 207910-84-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-(4-fluorophenyl)-2-hydroxyacrylic acid
• 英文别名: 3-(4-Fluorophenyl)-2-hydroxyacrylic acid；(Z)-3-(4-fluorophenyl)-2-hydroxyprop-2-enoic acid
• CAS: 207910-84-7
• 化学式: C₉H₇FO₃
• 分子量: 182.151
• InChiKey: SOBWLKLZARZQOX-YVMONPNESA-N

物化性质

• 沸点：
  341.2±42.0 °C(Predicted)
• 密度：
  1.439±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-3-(4-fluorophenyl)-2-hydroxyacrylic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.5h， 生成 (Z)-3-(4-fluorophenyl)-2-methoxy-N-phenylacrylamide
  参考文献：
  名称：

  Synthesis of novel cinnamanilides as potential immunosuppressive agents

  摘要：

  A series of new cinnamanilides (6-40) were synthesized and their immunosuppressive activity and cytotoxicity were evaluated. Most of the cinnamanilides showed good immunosuppressive activity. Among the synthesized compounds, (Z)-N-(4-bromophenyl)-2-methoxy-3-(4-methoxyphenyl)acrylamide (37) and (Z)-2-methoxy-3-(4-methoxyphenyl)-N-p-tolylacrylamide (38) exhibited potent immunosuppressive activity (IC50 = 1.77 +/- 0.33 and 0.94 +/- 0.13 mu M) without significant cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.027
• 作为产物：
  描述：

  2-methyl-4-(4-fluorophenylmethylene)-5(4H)-oxazolone 在 盐酸 、 水 作用下， 反应 3.0h， 以72%的产率得到(Z)-3-(4-fluorophenyl)-2-hydroxyacrylic acid
  参考文献：
  名称：

  Synthesis of novel cinnamanilides as potential immunosuppressive agents

  摘要：

  A series of new cinnamanilides (6-40) were synthesized and their immunosuppressive activity and cytotoxicity were evaluated. Most of the cinnamanilides showed good immunosuppressive activity. Among the synthesized compounds, (Z)-N-(4-bromophenyl)-2-methoxy-3-(4-methoxyphenyl)acrylamide (37) and (Z)-2-methoxy-3-(4-methoxyphenyl)-N-p-tolylacrylamide (38) exhibited potent immunosuppressive activity (IC50 = 1.77 +/- 0.33 and 0.94 +/- 0.13 mu M) without significant cytotoxicity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.027

文献信息

• [EN] N-(HETEROCYCLYL AND HETEROCYCLYLALKYL)-3-BENZYLPYRIDIN-2-AMINE DERIVATIVES AS SSTR4 AGONISTS<br/>[FR] DÉRIVÉS DE N-(HÉTÉROCYCLYL ET HÉTÉROCYCLYLALKYL)-3-BENZYLPYRIDIN-2-AMINE SERVANT D'AGONISTES DE SSTR4
  申请人：TAKEDA PHARMACEUTICALS CO

  公开号：WO2021202775A1

  公开（公告）日：2021-10-07

  Disclosed are compounds of Formula (1), and pharmaceutically acceptable salts thereof, wherein n, R1, R4, R5, R6, R7, R8, R9, R10, R11, R14, X2, X3 and X12 are defined in the specification. This disclosure also relates to materials and methods for preparing compounds of Formula (1), to pharmaceutical compositions which contain them, and to their use for treating diseases, disorders, and conditions associated with SSTR4.

  披露了公式（1）的化合物，以及其中n、R1、R4、R5、R6、R7、R8、R9、R10、R11、R14、X2、X3和X12在说明书中定义的药用可接受盐。本公开还涉及用于制备公式（1）化合物的材料和方法，含有它们的药物组合物，以及它们用于治疗与SSTR4相关的疾病、障碍和状况。
• An<i>Atropos</i>Biphenyl Bisphosphine Ligand with 2,2′-<i>tert</i>-Butylmethylphosphino Groups for the Rhodium-Catalyzed Asymmetric Hydrogenation of Enol Esters
  作者：Jia Jia、Dongyang Fan、Jian Zhang、Zhenfeng Zhang、Wanbin Zhang

  DOI：10.1002/adsc.201800774

  日期：2018.10.4

  calculations described in our previous work. This P‐stereogenic bisphosphine ligand possessing a biphenyl backbone and 2,2′‐tert‐butylmethylphosphino groups has been applied to the Rh‐catalyzed asymmetric hydrogenation of enol esters, which has not been widely studied and can be used for the synthesis of several important bioactive compounds. Although there is room for further improvement in enantioselectivity

  这是我们先前有关Atropos联苯双膦配体开发的工作的更新。单晶X射线衍射证实了Atropos出乎意料的结构性能，该结果与我们先前工作中所述的计算结果相符。这种具有联苯骨架和2,2'-叔丁基甲基膦基的P-stereogenic bisphosphine配体已被用于Rh催化的烯醇酯的不对称加氢反应，尚未得到广泛研究，可用于合成几种重要的生物活性化合物。尽管在对映选择性方面仍有进一步改进的余地，但本文报道的结果提供了对这类配体的进一步理解。
• Enantioselective synthesis of non-natural amino acids using phenylalanine dehydrogenases modified by site-directed mutagenesis
  作者：Patricia Busca、Francesca Paradisi、Eamonn Moynihan、Anita R. Maguire、Paul C. Engel

  DOI：10.1039/b406364c

  日期：——

  The substrate scope of three mutants of phenylalanine dehydrogenase as biocatalysts for the transformation of a series of 2-oxo acids, structurally related to phenylpyruvic acid, to the analogous α-amino acids, non-natural analogues of phenylalanine, has been investigated. The mutant enzymes are more tolerant than the wild type enzyme of the non-natural substrates, especially those with substituents at the 4-position on the phenyl ring. Excellent enantiocontrol resulted in all cases.

  三个变种的苯丙氨酸脱氢酶作为生物催化剂，用于将一系列与苯丙酮酸结构相关的2-氧酸转化为相应的α-氨基酸，即苯丙氨酸的非天然类似物，其底物范围已被研究。这些变种酶比野生型酶更能容忍非天然底物，特别是那些在苯环的4-位有取代基的底物。在所有情况下，都表现出了优秀的对映选择性。
• Single-Biocatalyst Synthesis of Enantiopure<scp>d</scp>-Arylalanines Exploiting an Engineered<scp>d</scp>-Amino Acid Dehydrogenase
  作者：Fabio Parmeggiani、Syed T. Ahmed、Matthew P. Thompson、Nicholas J. Weise、James L. Galman、Deepankar Gahloth、Mark S. Dunstan、David Leys、Nicholas J. Turner

  DOI：10.1002/adsc.201600682

  日期：2016.10.20

  A practical and efficient biocatalytic synthesis of aromatic d‐amino acids has been developed, based on the reductive amination of the corresponding α‐keto acids via a recombinant whole cell system composed of an engineered dehydrogenase and cofactor recycling apparatus. The reaction was shown to give excellent enantioselectivity (≥98%) and good yields at the preparative scale across a broad range

  基于相应的α-酮酸通过由工程脱氢酶和辅因子回收装置组成的重组全细胞系统的还原胺化反应，已开发出一种实用，有效的芳香族d-氨基酸生物催化合成方法。结果表明，在制备规模上，该反应在多种底物上均具有出色的对映选择性（≥98％）和良好的收率。另外，解析了变体酶的结构以使观察到的反应速率合理化。工程化的全细胞催化剂还通过与对映体互补脱氨酶结合使用，来介导外消旋混合物和更便宜的l-氨基酸产生的d-苯丙氨酸衍生物。
• Synthesis and biological activities of a series of 4,5-diaryl-3-hydroxy-2(5H)-furanones
  作者：Fabrice Bailly、Clémence Queffélec、Gladys Mbemba、Jean-François Mouscadet、Nicole Pommery、Jean Pommery、Jean-Pierre Hénichart、Philippe Cotelle

  DOI：10.1016/j.ejmech.2007.08.005

  日期：2008.6

  A series of thirteen 4,5-diaryl-3-hydroxy-2(5H)-furanones were synthesized. They were evaluated for their antioxidant potencies and inhibitory properties of 5-lipoxygenase, cyclooxygenases, HIV-1 integrase and PC3 cell proliferation. New hits were discovered either in the anti-proliferation test or in the HIV anti-integrase test. (c) 2007 Elsevier Masson SAS. All rights reserved.

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