(3-硝基苯基)甲基苯甲酸酯 | 38612-16-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (3-硝基苯基)甲基苯甲酸酯
• 英文名称: 3-nitrobenzyl benzoate
• 英文别名: (3-nitrophenyl)methyl benzoate
• CAS: 38612-16-7
• 化学式: C₁₄H₁₁NO₄
• 分子量: 257.246
• InChiKey: XYHCAQKUZAEVJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2916310090

反应信息

• 作为反应物：
  描述：

  (3-硝基苯基)甲基苯甲酸酯 在 乙醚 、 aluminium amalgam 作用下， 生成 Benzoeseure-(3-aminobenzylester)
  参考文献：
  名称：

  Niyogy, Journal of the Indian Chemical Society, 1930, vol. 7, p. 577,583

  摘要：

  DOI：
• 作为产物：
  描述：

  反应 8.0h， 生成 (3-硝基苯基)甲基苯甲酸酯
  参考文献：
  名称：

  氢键辅助的无过渡金属催化酰胺转化为酯

  摘要：

  酰胺CN的裂解在合成化学，生物过程和制药工业中引起了广泛的兴趣。过渡金属，豪华配体或过量的碱对转化始终至关重要。在这里，我们开发了仅催化量碱的无过渡金属的氢键助酰胺化酰胺。控制实验，密度泛函理论（DFT）计算和动力学研究支持了氢键在协助酯化中所起的关键作用。除了广泛的底物范围和出色的官能团耐受性外，该碱催化方案还补充了传统的过渡金属催化的酰胺酯化反应，并为有机合成和制药行业催化裂解酰胺CN键提供了新途径。

  DOI：

  10.1007/s11426-020-9883-3

文献信息

• Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols
  作者：Iraj Mohammadpoor-Baltork、Hamid Aliyan、Ahmad Reza Khosropour

  DOI：10.1016/s0040-4020(01)00521-x

  日期：2001.7

  Efficient acetylation and benzoylation of alcohols and phenols with acetic and benzoic anhydrides have been carried out under catalysis of bismuth(III) salts including BiCl3, Bi(TFA)3 and Bi(OTf)3. Selective acetylation and benzoylation of alcohols in the presence of phenols is an additional advantage of this procedure.

  在包括BiCl 3，Bi（TFA）3和Bi（OTf）3的铋（III）盐的催化下，已经进行了醇和酚与乙酸酐和苯甲酸酐的有效乙酰化和苯甲酰化。在酚存在下，醇的选择性乙酰化和苯甲酰化是该方法的另一个优点。
• Comprehensive Study of the Organic-Solvent-Free CDI-Mediated Acylation of Various Nucleophiles by Mechanochemistry
  作者：Thomas-Xavier Métro、Julien Bonnamour、Thomas Reidon、Anthony Duprez、Jordi Sarpoulet、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/chem.201501325

  日期：2015.9.1

  in the synthesis of natural products and biologically active compounds. Unfortunately, these reactions often require the use of large quantities of volatile and/or toxic solvents, either for the reaction, purification or isolation of the products. Herein we describe and discuss the possibility of completely eliminating the use of organic solvents for the synthesis, purification and isolation of products

  酰化反应在天然产物和生物活性化合物的合成中无处不在。不幸的是，这些反应通常需要使用大量的挥发性和/或有毒溶剂，用于反应，纯化或分离产物。本文中，我们描述和讨论了完全消除有机溶剂用于合成，纯化和分离由胺和其他亲核试剂酰化产生的产物的可能性。因此，利用N，N'羰基二咪唑（CDI）可在无溶剂机械搅拌下实现羧酸与各种亲核试剂之间的高效偶联，而水助研磨可实现纯产物的纯化和分离。分析和讨论了关键参数，例如产品的物理状态和水溶性，研磨材料，搅拌类型（振动或行星式搅拌）以及磨损造成的污染。此外，提出了原始的无溶剂有机溶剂条件，以克服这种方法的局限性。其中包括各种绿色指标的计算，突出了此策略对环境的影响特别小。
• Synthesis, characterization and catalytic performances of benzimidazolin-2-iminato actinide (IV) complexes in the Tishchenko reactions for symmetrical and unsymmetrical esters
  作者：Heng Liu、Maxim Khononov、Natalia Fridman、Matthias Tamm、Moris S. Eisen

  DOI：10.1016/j.jorganchem.2017.09.020

  日期：2018.2

  benzimdazolin-2-iminato actinide−(IV) complexes [(Bim7-MeDipp/MeN)An(N(SiMe3)2)3] (An = U (3), Th (4)) and [(Bim4-MeDipp/MeN)An(N(SiMe3)2)3] (An = U (5), Th (6)) were synthesized and their solid state structures were established by single-crystal X-ray diffraction analysis. The catalytic performances of complexes 3–6 towards the homo- and cross-coupling of aldehydes (Tishchenko reaction) were studied and the thorium

  苯并咪唑啉-2-亚氨基to系-（IV）络合物的新家族[（Bim 7-Me Dipp / Me N）An（N（SiMe 3）2）3 ]（An = U（3），Th（4））和[（Bim 4-Me Dipp / Me N）An（N（SiMe 3）2）3 ]（An = U（5），Th（6））合成，并通过单晶X建立其固态结构射线衍射分析。研究了配合物3 – 6对醛的均相和交叉偶联（Tishchenko反应）的催化性能，并研究了complex配合物图4和图6显示出产生相应的对称和不对称酯的中等至高活性。这些th配合物还研究了醛与醇的偶联，称为串联质子转移酯化，以及醛与三氟甲基酮之间的分子间偶联反应，表明了选择性地获得不对称酯的互补方法。这些反应的合理机制是基于化学计量研究提出的。
• ——
  作者：Iraj Mohammadpoor-Baltork、Ahmad R. Khosropour

  DOI：10.1007/s706-002-8249-1

  日期：2002.2

  A variety of TMS and THP ethers are efficiently converted to their corresponding acetates and benzoates with acetic and benzoic anhydrides in the presence of catalytic amounts of Bi(III) salts such as BiCl3, Bi(TFA)(3), and Bi(OTf)(3). The present method is also effective for the selective acetylation and benzoylation of TMS and THP ethers of alcohols in the presence of phenolic ethers.
• Inhibitory effects of benzyl benzoate and its derivatives on angiotensin II-induced hypertension
  作者：Osamu Ohno、Mao Ye、Tomoyuki Koyama、Kazunaga Yazawa、Emi Mura、Hiroshi Matsumoto、Takao Ichino、Kaoru Yamada、Kazuhiko Nakamura、Tomohiro Ohno、Kohji Yamaguchi、Junji Ishida、Akiyoshi Fukamizu、Daisuke Uemura

  DOI：10.1016/j.bmc.2008.03.056

  日期：2008.8

  Hypertension is a lifestyle-related disease which often leads to serious conditions such as heart disease and cerebral hemorrhage. Angiotensin II (Ang II) plays an important role in regulating cardiovascular homeostasis. Consequently, antagonists that block the interaction of Ang II with its receptors are thought to be effective in the suppression of hypertension. In this study, we searched for plant compounds that had antagonist-like activity toward Ang II receptors. From among 435 plant samples, we found that EtOH extract from the resin of sweet gum Liquidambar styraciflua strongly inhibited Ang II signaling. We isolated benzyl benzoate and benzyl cinnamate from this extract and found that those compounds inhibited the function of Ang II in a dose-dependent manner without cytotoxicity. An in vivo study showed that benzyl benzoate significantly suppressed Ang II-induced hypertension in mice. In addition, we synthesized more than 40 derivatives of benzyl benzoate and found that the meta-methyl and 3-methylbenzyl 2'-nitrobenzoate derivatives showed about 10-fold higher activity than benzyl benzoate itself. Thus, benzyl benzoate, its derivatives, and benzyl cinnamate may be useful for reducing hypertension. (c) 2008 Elsevier Ltd. All rights reserved.