(4-硝基苯基)庚酸酯 | 1956-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: (4-硝基苯基)庚酸酯
• 英文名称: p-nitrophenyl heptanoate
• 英文别名: 4-Nitrophenyl heptanoate；(4-nitrophenyl) heptanoate
• CAS: 1956-08-7
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: UUQDIYZHZCSSEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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-硝基苯基)庚酸酯 在 Carbonate buffer 作用下， 以 水 为溶剂， 生成 庚酸酯
  参考文献：
  名称：

  CYCLODEXTRIN-CATALYZED HYDROLYSIS OF ESTERS BEARING A HYDROPHOBIC TAIL

  摘要：

  与短烷基链的对硝基苯酯相比，γ-环糊精催化的长烷基链对硝基苯酯水解的速率加速度更大。而在β-环糊精中则没有观察到这种速率加速行为。结果表明，具有长烷基链的酯类在 γ-环糊精空腔中具有折叠结构（A 型）。

  DOI：

  10.1246/cl.1985.159
• 作为产物：
  描述：

  对己酸对硝基苯酯 在 吡啶 、 erythromycin A-hydrolyse prod. 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 (4-硝基苯基)庚酸酯
  参考文献：
  名称：

  Barra, Monica; Rossi, Rita H. de, Journal of Chemical Research, Miniprint, 1992, # 7, p. 1758 - 1772

  摘要：

  DOI：

文献信息

• Antibody catalyzed modification of amino acids. Efficient hydrolysis of tyrosine benzoate
  作者：Fabio Benedetti、Federico Berti、Massimiliano Flego、Silvia Peressini、Alfonso Colombatti、Lucia Gardossi、Paolo Linda

  DOI：10.1039/b100450f

  日期：——

  Esterase antibody 522c2, the first example of a catalytic antibody specifically programmed to control the reactivity of functional groups on the side chain of tyrosine, accelerates the hydrolysis of benzoate esters of L-tyrosine and tyrosine-containing dipeptides by a factor of 104 and is moderately active against other benzoate esters.

  酯酶抗体522c2是首个被特异性编程以调控酪氨酸侧链上功能团反应活性的催化抗体，它以104倍的速度加速L-酪氨酸及其含酪氨酸二�肽的苯甲酸酯的水解，并对其他苯甲酸酯表现出中等活性。
• Transition state stabilization by micelles: thiolysis of <i>p</i>-nitrophenyl alkanoates in cetyltrimethylammonium bromide micelles
  作者：Oswald S Tee、Ogaritte J Yazbeck

  DOI：10.1139/v00-113

  日期：2000.8.1

  Thiolysis of p-nitrophenyl esters (acetate to decanoate) by the anion of 2-mercaptoethanol (ME) is catalyzed by micelles of cetyltrimethylammonium bromide (CTAB) in aqueous solution. At fixed [ME], the observed rate constants (k_obs) show saturation with respect to added [CTAB], consistent with ester binding in the micelles. Plots of k_obs vs. [ME] are linear in the absence and in the presence of the CTAB, and analysis of the slopes of the plots afford rates constants for thiolate ion attack on the esters in the aqueous phase (k_N) and in the micellar phase (k_cN). The strengths of substrate binding and transition state binding to the micelles are strongly correlated, with a slope of unity, because they have the same dependence on the ester chain. Consequently, the catalytic ratios (k_cN/k_N) are independent of the length of the ester. Similar behaviour is found for thiolysis by the dianions of mercaptoacetic acid, 3-mercaptopropionic acid, and cysteine, and also for ester cleavage by the anions of glycine and 2,2,2-trifluoroethanol, as earlier for cleavage by hydroxide ion. The results are consistent with Kirby's dissection of transition state binding into "passive" and "dynamic" components. The passive component involves hydrophobic binding of the ester chain which is more or less the same as in the substrate binding. The dynamic component is associated with reaction in the Stern layer of the micelle, and its magnitude varies with the nucleophiles because of differences in their ease of exchange between the aqueous medium and the Stern layer.Key words: catalysis, esters, thiolysis, micelles.

  对2-巯基乙醇（ME）的阴离子在十溴化十六烷基三甲基铵（CTAB）的胶团催化下，在水溶液中催化对硝基苯酚酯（乙酸至癸酸）的硫醇解。在固定的[ME]下，观察到的速率常数（k_obs）随着添加的[CTAB]呈饱和状态，与酯在胶团中的结合一致。k_obs vs. [ME]的图表在没有CTAB和有CTAB的情况下是线性的，分析图表的斜率可得到水相中对酯的硫醇离子攻击速率常数（k_N）和胶团相中的速率常数（k_cNcN/k_N）与酯的长度无关。对巯基乙酸、3-巯基丙酸和半胱氨酸的二阴离子进行硫醇解，以及甘氨酸和2,2,2-三氟乙醇的阴离子进行酯裂解，与氢氧根离子裂解相似。结果与柯比对过渡态结合的解剖“被动”和“动态”成分一致。被动成分涉及酯链的疏水结合，与底物结合几乎相同。动态成分与胶团的Stern层中的反应相关，并且其大小随着亲核试剂的不同而变化，因为它们在水介质和Stern层之间的交换难易程度不同。关键词：催化，酯，硫醇解，胶团。
• Transition state stabilization by micelles: the hydrolysis of <i>p</i>-nitrophenyl alkanoates in cetyltrimethylammonium bromide micelles
  作者：Oswald S. Tee、Alexei A. Fedortchenko

  DOI：10.1139/v97-172

  日期：1997.10.1

  independent of the ester chain. These and earlier results are consistent with the reaction centre being located in the Stern layer of the micelle, with the acyl chain of the ester being directed into the hydrophobic micellar interior. The chain length dependence of kinetic parameters found in this work is comparable to that found previously for ester cleavage by cyclodextrins and by various enzymes with

  在高 pH 值下对硝基苯基链烷酸酯（乙酸酯至辛酸酯）的裂解是由十六烷基三甲基溴化铵 (CTAB) 在水溶液中形成的胶束适度催化的。速率常数表现出相对于 [CTAB] 的饱和行为，与胶束中的底物结合一致。底物结合和过渡态结合到胶束的强度随着酰基链长度的增加而单调增加，并且具有完全相同的灵敏度。因此，加速程度（或催化比率）与酯链无关。这些和早期的结果与反应中心位于胶束的斯特恩层一致，酯的酰基链被引导到疏水胶束内部。
• Catalytic properties of novel cyclodextrin dimers in the hydrolytic cleavage ofp-nitrophenyl alkanoates
  作者：Mei-Ming Luo、Ru-Gang Xie、Ping-Fang Xia、Ling Tao、De-Qi Yuan、Hua-Ming Zhao

  DOI：10.1002/poc.379

  日期：2001.8

  Novel cyclodextrin (CD) dimers (3a–c) linked by multidentate ligands were prepared by reacting 6-deoxy-6-(hydroxyethylamino)-β-CD (2) with p- and m-bis(bromomethyl)benzene and 2,6-bis(bromomethyl)pyridine, respectively. The catalytic properties of 2, 3b and 3c in the hydrolytic cleavage of p-nitrophenyl alkanoates, namely acetate (PNPA), butanoate (PNPB), hexanoate (PNPH) and octanoate (PNPO), were

  新颖的环糊精（CD）二聚体（3A-C通过齿配体连接）由6-脱氧-6-（羟基乙基氨基）反应，制备-β-CD（2）与p -和米双（溴甲基）苯和2,6- -双（溴甲基）吡啶。的催化性质2，图3b和图3c中的水解裂解p硝基苯基链烷酸酯，即乙酸酯（PNPA），丁酸乙酯（PNPB），己酸盐（PNPH）和辛酸（PNPO），进行了研究。CD二聚体3b和3c在中性附近显示出适度的速率增强。尽管在3b存在下催化速率常数（k c）或3c随酯链长度的变化不显着，“长链”酯（PNPH和PNPO）的米氏常数K M远小于“短链”酯（PHPA和PNPB）的米氏常数，因此，“长链”酯的选择性因子（k c / K M）比“短链”酯的选择性因子大得多，这表明CD二聚体在水解过程中具有良好的尺寸识别能力和底物选择性。对硝基苯基链烷酸酯。向反应介质中添加Cu 2+对K M的影响不大，但导致K M的显着增加。ķ Ç在，因此增加ķ Ç
• FLUORESCENT PROBES FOR DNA DETECTION BY HYBRIDIZATION WITH IMPROVED SENSITIVITY AND LOW BACKGROUND
  申请人：Lokhov Sergey

  公开号：US20080293586A1

  公开（公告）日：2008-11-27

  Minor groove binder-oligonucleotide probes are provided along with methods for their use wherein the probes have an attached fluorophore which, in an unhybridized form exhibits very low background signal.

  提供了微小沟结合剂寡核苷酸探针以及其使用方法，其中探针具有附加的荧光物质，未杂交形式的荧光物质信号非常低。