4-硝基-1-萘基乙酸酯 | 6549-14-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 4-硝基-1-萘基乙酸酯
• 英文名称: 4-nitro-1-naphthyl acetate
• 英文别名: (4-Nitronaphthalen-1-yl) acetate
• CAS: 6549-14-0
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: DYIWFHGPUXIKED-UHFFFAOYSA-N

物化性质

• 沸点：
  392.8±25.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-1-萘基乙酸酯 在 a cyclophane hydrolysis 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 4-硝基-1-萘酚
  参考文献：
  名称：

  催化环烷VII。双咪唑基-环烷的酯酶活性

  摘要：

  我们报告了具有两个咪唑残基的新型四氧杂[6.1.6.1]对环环烷3的合成，该残基连接到形成大环腔的两个二苯甲烷间隔基之一的苯环上。四个乙酸残基与两个间隔单元的中心碳原子分开，并确保3在水和二元水性溶剂混合物中的溶解度。环戊烷3在含水磷酸盐缓冲液（pH 8）中与乙酸硝基萘酯形成化学计量的包合物，并在周转条件下催化结合的底物的水解。

  DOI：

  10.1002/recl.19931120605
• 作为产物：
  描述：

  萘酚 在 吡啶 、 sodium nitrate 、 benzyltriphenylphosphonium peroxodisulfate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 4-硝基-1-萘基乙酸酯
  参考文献：
  名称：

  The relevance of K i calculation for bi-substrate enzymes illustrated by kinetic evaluation of a novel lysine (K) acetyltransferase 8 inhibitor

  摘要：

  Histone acetyltransferases (HATs) are important mediators of epigenetic post-translational modifications of histones that play important roles in health and disease. A disturbance of these modifications can result in disease states, such as cancer or inflammatory diseases. Inhibitors of HATs (HATi) such as lysine (K) acetyltransferase 8 (KAT8), could be used to study the epigenetic processes in diseases related to these enzymes or to investigate HATs as therapeutic targets. However, the development of HATi is challenged by the difficulties in kinetic characterization of HAT enzymes and their inhibitors to enable calculation of a reproducible inhibitory potency. In this study, a fragment screening approach was used, enabling identification of 4-amino-1-naphthol, which potently inhibited KAT8. The inhibitor was investigated for enzyme inhibition using kinetic and calorimetric binding studies. This allowed for calculation of the K-i values for both the free enzyme as well as the acetylated intermediate. Importantly, it revealed a striking difference in binding affinity between the acetylated enzyme and the free enzyme, which could not be revealed by the IC50 value. This shows that kinetic characterization of inhibitors and calculation of K-i values is crucial for determining the binding constants of HAT inhibitors. We anticipate that more comprehensive characterization of enzyme inhibition, as described here, is needed to advance the field of HAT inhibitors. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.05.015

文献信息

• Enzymatic Cleavage of Aryl Acetates
  作者：Marcel Bauch、Dominique Böttcher、Uwe T. Bornscheuer、Torsten Linker

  DOI：10.1002/cctc.201600678

  日期：2016.9.7

  the cleavage of aryl acetates. Phenyl and naphthyl acetates react with lipases and esterases, whereas the sterically demanding anthracene acetate gave a conversion only with porcine liver esterase and esterase 2 from Bacillus subtilis (BS2) . These two enzymes have been employed on a preparative (0.5 mmol) scale and afforded cleavage products in 91 and 94 % yields, even for anthracene acetate. Thus

  已经筛选了七个酶来切割乙酸芳基酯。苯基乙酸萘酯和萘乙酸酯与脂肪酶和酯酶反应，而对空间要求苛刻的蒽乙酸酯仅与猪肝酯酶和枯草芽孢杆菌的酯酶2发生转化（BS2）。这两种酶已在制备型（0.5 mmol）规模上使用，即使对于乙酸蒽，也能以91％和94％的产率提供裂解产物。因此，该方法优于用催化量的甲醇钠进行化学裂解（Zemplén条件），后者的转化率很低。最后，用蒽双乙酸酯实现了区域选择性，其中乙基控制第一乙酸酯的裂解。这表明空间相互作用在乙酸芳基酯的酶促裂解中起关键作用，这对于将来的应用或酶抑制剂的开发可能是令人感兴趣的。
• The Stereoselective Retardation of the Alkaline Hydrolysis of Organic Esters by Binuclear Cu(II) Complexes with Cyclodextrins
  作者：Yoshihisa Matsui、Daisuke Suemitsu

  DOI：10.1246/bcsj.58.1658

  日期：1985.6

  The alkaline hydrolysis of p-nitrophenyl acetate (p-NPA) in 1.0mol dm−3 NaOH at 25 °C was almost completely retarded by the addition of a binuclear Cu(II) complex with α-cyclodextrin (Cu2α-CD). The dissociation constant for an inclusion complex of Cu2α-CD with p-NPA was determined to be 0.059 mmol dm−3, which is about one 200th that for an inclusion complex of α-CD with p-NPA. The alkaline hydrolysis of o- and m-nitrophenyl acetates was also retarded by Cu2α-CD, though the extent of retardation was much less than that for p-NPA. A binuclear Cu(II) complex with β-cyclodextrin (Cu2β-CD) also caused a stereoselective deceleration of the alkaline hydrolysis of the esters. However, the stereoselectivity of Cu2β-CD was not so remarkable as that of Cu2α-CD. Dissociation constants for inclusion complexes of Cu2α2-CD with several alcohols and other organic substrates were determined by the kinetic examination of the competitive inhibition effect of the substrates on the association of Cu2α-CD with p-NPA. Cu2α-CD formed stable inclusion complexes with such disk-like molecules as cyclohexanol, cycloheptanol, and p-nitrobenzyl alcohol. The geometry of a Cu2α-CD-p-NPA inclusion complex was presumed on the basis of these results.

  对硝基苯乙酸酯（p-NPA）在 1.0mol dm-3 NaOH 溶液（25 °C）中的碱性水解几乎完全被加入α-环糊精（Cu2α-CD）的双核 Cu（II）络合物所延缓。经测定，Cu2α-CD 与 p-NPA 的包合络合物的解离常数为 0.059 mmol dm-3，约为α-CD 与 p-NPA 的包合络合物解离常数的 200 分之一。Cu2α-CD 也能延缓邻硝基苯乙酸酯和间硝基苯乙酸酯的碱性水解，但延缓程度远小于对硝基苯酚的延缓程度。Cu(II) 与 β-环糊精的双核配合物（Cu2β-CD）也会导致酯类碱性水解的立体选择性减速。不过，Cu2β-CD 的立体选择性不如 Cu2α-CD 那么显著。通过对底物对 Cu2α-CD 与 p-NPA 结合的竞争性抑制作用进行动力学检验，确定了 Cu2α2-CD 与几种醇和其他有机底物的包合复合物的解离常数。Cu2α-CD 与环己醇、环庚醇和对硝基苯甲醇等盘状分子形成了稳定的包合物。根据这些结果推测了 Cu2α-CD-p-NPA 包合物的几何形状。
• Hydroxylation of Nitrated Naphthalenes with KO2/Crown Ether.
  作者：Kiyoshi FUKUHARA、Yukie HARA、Ikuo NAKANISHI、Naoki MIYATA

  DOI：10.1248/cpb.48.1532

  日期：——

  Superoxide radical anion (O·-2), generated by KO2/crown ether, is effective for hydroxylation of nitronaphthalenes. When mono- and di-nitronaphthalenes are treated with KO2/crown ehter, hydroxylation results at the electron-deficient site caused by the electron withdrawing effect of the substituted nitro group. Kinetic experiments suggest that the hydroxylation proceeds by two different mechanisms dependent on the first one-electron reduction potential of nitronaphthalenes.

  由 KO2/冠醚生成的超氧自由基阴离子（O--2）可有效地对硝基萘进行羟基化。当用 /冠醚处理一硝基和二硝基萘时，由于取代的硝基的退电子效应，在缺电子位点发生羟基化反应。动力学实验表明，羟基化作用有两种不同的机制，取决于硝基萘的第一单电子还原电位。
• Designed water-soluble macrocyclic esterases: from nonproductive to productive binding
  作者：Francois Diederich、Gregor Schuermann、Ito Chao

  DOI：10.1021/jo00247a017

  日期：1988.6
• Ananthakrishna Nadar; Rajarathinam, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1997, vol. 36, # 9, p. 749 - 753
  作者：Ananthakrishna Nadar、Rajarathinam

  DOI：——

  日期：——