4-nitrophenyl cyclopropanecarboxylate | 26050-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-nitrophenyl cyclopropanecarboxylate
• 英文别名: p-nitrophenyl cyclopropanecarboxylate；methyl 1-(4-nitrophenyl)cyclopropanecarboxylate；Cyclopropancarbonsaeure-p-nitrophenylester；Cyclopropanecarboxylic acid, 4-nitrophenyl ester；(4-nitrophenyl) cyclopropanecarboxylate
• CAS: 26050-99-7
• 化学式: C₁₀H₉NO₄
• mdl: MFCD25969981
• 分子量: 207.186
• InChiKey: KYHAMGAANHSNPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  342.2±25.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)
• 保留指数：
  1695

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl cyclopropanecarboxylate 在 4-二甲氨基吡啶 、 Bacillus subtilis 168 SrfAD esterase 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 40.25h， 生成 4-硝基苯基乙酸酯
  参考文献：
  名称：

  Fingerprint lipolytic enzymes with chromogenic p-nitrophenyl esters of structurally diverse carboxylic acids

  摘要：

  A series of structurally diverse chromogenic esters, including a new compound (4-nitrophenyl 2-methylpentanoate), has been synthesized, constituting an array of 17 substrates which could be applied to rapidly fingerprint the activity of lipases or esterases to reveal their substrates specificity and functional characteristics. Combined with genetic technology such as "data mining" and directed evolution, such fingerprints might be a promising platform for discovery of potentially useful enzymes in industrial application. The fingerprint of commercially available Lipase-B from Candida antarctica as a model enzyme was first measured to confirm the reliability of this method. Then three new enzymes mined from genomic libraries were successfully fingerprinted, revealing the functional characteristics of those enzymes. Among them, the enzyme SrfAD was founded with specific substrate preference towards cycloalkyl carboxylic esters and aromatic esters, making it more promising in synthetic utilities than other tested enzymes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.07.010
• 作为产物：
  描述：

  4-硝基苯基硬脂酸酯 在 4-二甲氨基吡啶 、 Candida antarctica lipase B 、 Bacillus subtilis 168 SrfAD esterase 、 N,N'-二环己基碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 48.3h， 生成 4-nitrophenyl cyclopropanecarboxylate
  参考文献：
  名称：

  Fingerprint lipolytic enzymes with chromogenic p-nitrophenyl esters of structurally diverse carboxylic acids

  摘要：

  A series of structurally diverse chromogenic esters, including a new compound (4-nitrophenyl 2-methylpentanoate), has been synthesized, constituting an array of 17 substrates which could be applied to rapidly fingerprint the activity of lipases or esterases to reveal their substrates specificity and functional characteristics. Combined with genetic technology such as "data mining" and directed evolution, such fingerprints might be a promising platform for discovery of potentially useful enzymes in industrial application. The fingerprint of commercially available Lipase-B from Candida antarctica as a model enzyme was first measured to confirm the reliability of this method. Then three new enzymes mined from genomic libraries were successfully fingerprinted, revealing the functional characteristics of those enzymes. Among them, the enzyme SrfAD was founded with specific substrate preference towards cycloalkyl carboxylic esters and aromatic esters, making it more promising in synthetic utilities than other tested enzymes. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.07.010

文献信息

• Substituent effects on the activation parameters of pyridine acylation with esters and thioesters in solution
  作者：V. M. Vlasov

  DOI：10.1134/s1070428013030135

  日期：2013.3

  Variation of the activation parameters in the acylation of pyridine with esters and thioesters may be used as a tool for studying mechanisms of acyl transfer reactions in solution. Here, the effect of substituents in benzene and pyridine derivatives on the activation parameters ΔX ≠ (where X stands for enthalpy H, entropy S, or Gibbs energy G) in terms of an equation analogous to the Hammett equation

  吡啶与酯和硫酯的酰化反应中活化参数的变化可用作研究溶液中酰基转移反应机理的工具。在此，根据类似于哈米特方程的方程，使用苯和吡啶衍生物中的取代基对活化参数ΔX ≠（其中X表示焓H，熵S或吉布斯能量G）的影响。恒δΔ X ≠。反应常数δΔ的线性相关ħ ≠ INT上δΔ ģ ≠ 当该方法的一个步骤是唯一确定速率的步骤时，该方法提供了另一种评估吡啶酰化机理变化的方法。
• [EN] HETEROCYCLIC KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE HETEROCYCLIQUE
  申请人：ABBOTT LAB

  公开号：WO2004076424A1

  公开（公告）日：2004-09-10

  Compounds having the formula (I) are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  具有公式(I)的化合物对于抑制蛋白激酶是有用的。还公开了制造这些化合物的方法、包含这些化合物的组合物以及使用这些化合物的治疗方法。
• [EN] NOVEL ANTITHROMBOTIC AGENTS<br/>[FR] NOUVEAUX AGENTS ANTITHROMBOTIQUES
  申请人：CADILA HEALTHCARE LTD

  公开号：WO2011061760A1

  公开（公告）日：2011-05-26

  The present invention relates to novel derivatives of the general formula (I), their tautomeric forms, their stereoisomers, their pharmaceutically acceptable salts, pharmaceutical compositions containing them, methods for their preparation, use of these compounds in medicine and the intermediates involved in their preparation.

  本发明涉及通式（I）的新型衍生物，其互变异构体、立体异构体、药用盐、含有它们的药物组合物、其制备方法、这些化合物在医学上的用途以及其制备中涉及的中间体。
• Kinetics and mechanism of the aminolysis of phenyl cyclopropanecarboxylates in acetonitrile
  作者：Han Joong Koh、Chul Ho Shin、Hai Whang Lee、Ikchoon Lee

  DOI：10.1039/a801540f

  日期：——

  Kinetic studies of the reaction of Z-phenyl cyclopropanecarboxylates with X-benzylamines in acetonitrile at 55.0 °C have been carried out. The reaction proceeds by a stepwise mechanism in which the rate-determining step is the breakdown of the zwitterionic tetrahedral intermediate, T±, with a hydrogen-bonded four-center type transition state (TS). These mechanistic conclusions are drawn based on (i) the large magnitude of ρX and ρZ, (ii) the normal kinetic isotope effects (kH/kD > 1.0) involving deuterated benzylamine nucleophiles, (iii) the positive sign of ρXZ and the larger magnitude of ρXZ than that for normal SN2 processes, and lastly (iv) adherence to the reactivity–selectivity principle (RSP) in all cases.

  对 Z-苯基环丙烷羧酸盐与 X-苄胺在 55.0 °C乙腈中的反应进行了动力学研究。该反应通过一个逐步进行的机理进行，其中决定反应速率的步骤是齐聚四面体中间体 T± 与氢键四中心型过渡态 (TS) 的分解。得出这些机理结论的依据是：(i) ρX 和 ρZ 的数值较大；(ii) 涉及氘化苄胺亲核物的正常动力学同位素效应（kH/kD > 1.0）；(iii) ρXZ 的正负号和 ρXZ 的数值大于正常 SN2 过程的数值；最后，(iv) 在所有情况下都遵守反应选择性原理 (RSP)。
• DE1911520
  申请人：——

  公开号：——

  公开（公告）日：——