(R)-1-(3-硝基苯基)乙酸乙酯 | 103966-64-9

• 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: (R)-1-(3-硝基苯基)乙酸乙酯
• 英文名称: (R)-1-(3-nitrophenyl)ethyl acetate
• 英文别名: [(1R)-1-(3-nitrophenyl)ethyl] acetate
• CAS: 103966-64-9
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: BEQQFQIQGXVYEB-SSDOTTSWSA-N

物化性质

• 沸点：
  282.3±23.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  (R)-1-(3-硝基苯基)乙酸乙酯 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以94%的产率得到(R)-1-(3-硝基苯基)乙醇
  参考文献：
  名称：

  一锅动力学分辨率——Mitsunobu 反应以获得光学纯化合物，在替代方案中使用银盐

  摘要：

  通过一锅法、酶介导的 KR 和 Mitsunobu 与金属乙酸盐的反应，将外消旋甲醇转化为手性纯乙酸盐。使用 AoNO3 或与 NaOAc 的混合物得到了极好的结果。该协议进一步扩展以引入叠氮化物代替醋酸盐。

  DOI：

  10.1039/d0nj04802j
• 作为产物：
  描述：

  乙酸酐 、 (R)-1-(3-硝基苯基)乙醇 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-1-(3-硝基苯基)乙酸乙酯
  参考文献：
  名称：

  手性芳香醇的合成：使用含有手性二氨基环己烷配体的新型 C2-对称 RhIIICp*、RuII（伞花烃）或 RuII（苯）配合物作为不对称转移氢化催化剂

  摘要：

  摘要 使用衍生自 (1R,2R)-环己烷-1,2-二胺并与 [RhCl2Cp*]2 络合的 C2-对称双（磺酰胺）配体 (2)，通过不对称转移氢化 (ATH) 合成了 12 种手性仲醇， [RuCl2(cymene)]2 或 [RuCl2(苯)]2，然后原位用于还原前手性酮。以异丙醇作为氢源以 85-99% 的收率和 90-99% 的对映选择性获得醇。使用复合物 [RhCl2Cp*]2 和甲酸钠水溶液作为氢源，以 80-99% 的对映选择性实现了两倍的速率提高和更好的产率（88-99%）。

  DOI：

  10.1080/00397910802663451

文献信息

• Immobilized Manihot esculenta preparation as a novel biocatalyst in the enantioselective acetylation of racemic alcohols
  作者：Luciana L. Machado、Telma L.G. Lemos、Marcos Carlos de Mattos、Maria da Conceicão F. de Oliveira、Gonzalo de Gonzalo、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1016/j.tetasy.2008.05.018

  日期：2008.6

  The enzymatic preparation obtained from a discard of Manihot esculenta roots has been successfully immobilized on calcium alginate hydrogels. This preparation has been tested as a chiral biocatalyst in the enzymatic acylation of a set of racemic aromatic alcohols. Depending on the reaction conditions, excellent enantioselectivities can be achieved. Some parameters that can alter the biocatalytic properties of the enzyme, such as solvent, temperature, acyl donor and substrate structure have been studied exhaustively in order to establish a deeper knowledge of this novel biocatalyst. (C) 2008 Elsevier Ltd. All rights reserved.
• Escherichia coli BioH: a highly enantioselective and organic solvent tolerant esterase for kinetic resolution of sec-alcohols
  作者：Bo Wang、Xiaoling Tang、Ji Liu、Hongwei Yu

  DOI：10.1016/j.tetlet.2010.09.135

  日期：2010.12

  Escherichia coli BioH, which is obligatory for biotin synthesis, was found to be an organic solvent tolerant esterase with high enantioselectivity for the kinetic resolution of sec-alcohols using free enzyme powder. With this esterase, a variety of racemic sec-alcohols were efficiently resolved with ee values of up to 99%. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation
  作者：Koichiro Naemura、Masaki Murata、Rie Tanaka、Masashi Yano、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/0957-4166(96)00429-6

  日期：1996.11

  Lipase QL (from Alcaligenes sp.)-catalyzed acylation of alcohols using isopropenyl acetate as the acylating agent in diisopropyl ether converted preferentially primary alcohols with an S configuration and secondary alcohols with an R configuration into the corresponding homochiral acetates. On the basis of observed enantiomer selectivities, a predictive active site model for lipase QL is proposed for identifying which enantiomer of a primary or a secondary alcohol reacts faster in this acylation. Copyright (C) 1996 Published by Elsevier Science Ltd
• Potapov, V. M.; Dem'yanovich, V. M.; Khlebnikov, V. A., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 8, p. 1602 - 1606
  作者：Potapov, V. M.、Dem'yanovich, V. M.、Khlebnikov, V. A.、Koval'skaya, S. S.

  DOI：——

  日期：——
• Asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens
  作者：Nikos S. Hatzakis、Ioulia Smonou

  DOI：10.1016/j.bioorg.2005.05.002

  日期：2005.8

  A new asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens has been found. Although alcohols are not the natural substrates for this enzyme, a high R enantioselectivity was observed. Stereochemical studies showed that variations in substrate structure lead to strong variations in enantioselectivity. The highest enantioselectivities are obtained when the beta-carbon of the secondary alcohol is tertiary or quaternary. (c) 2005 Elsevier Inc. All rights reserved.