(+/-)-1-(3-nitrophenyl)ethyl acetate | 19759-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-1-(3-nitrophenyl)ethyl acetate
• 英文别名: 1-(3-Nitrophenyl)ethyl acetate
• CAS: 19759-28-5
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: BEQQFQIQGXVYEB-UHFFFAOYSA-N

物化性质

• 沸点：
  282.3±23.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(3-nitrophenyl)ethyl acetate 在 p-nitrobenzyl esterase from Bacillus subtilis 作用下， 以 aq. phosphate buffer 、 乙醇 为溶剂， 反应 4.0h， 以44%的产率得到1-(3-nitrophenyl)ethyl acetate
  参考文献：
  名称：

  Separation of enantiopure m-substituted 1-phenylethanols in high space-time yield using Bacillus subtilis esterase

  摘要：

  研究发现，在大肠杆菌中表达的重组枯草芽孢杆菌酯酶（BsE）在对映选择性水解反应中对 m-取代的 1-苯基乙醇乙酸酯表现出极好的对映选择性（E 始终大于 100）。分子模型为观察到的对这些底物的高对映选择性提供了解释。此外，BsE 还对高浓度的间取代 1-苯基乙醇乙酸酯（高达 1 M）表现出很强的耐受性。基于 BsE 的这些优异催化特性，一种间代 1-苯基乙醇--(R)-1-(3-氯苯基)乙醇被高效合成，时空产率为 920 克/升/天，ee 为 97%，这表明 BsE 被认为是大规模生产具有光学活性的间代 1-苯基乙醇的一种潜在的理想和有前途的生物催化剂。

  DOI：

  10.1039/c3ra41999a
• 作为产物：
  描述：

  间硝基苯甲醛 在 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 (+/-)-1-(3-nitrophenyl)ethyl acetate
  参考文献：
  名称：

  Asymmetric transesterification of secondary alcohols catalyzed by feruloyl esterase from Humicola insolens

  摘要：

  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.

  DOI：

  10.1016/j.bioorg.2005.05.002

文献信息

• Reaction of Hydrazones with Methoxy(tosyloxy)iodobenzene (MTIB): Tosylate Formation under Oxidative Conditions
  作者：Christopher Ramsden、Helen Rose

  DOI：10.1055/s-1997-702

  日期：——

  Treatment of aromatic hydrazones 1 containing electron-withdrawing, reduction sensitive substituents with MTIB gives the corresponding tosylates 2 in high yield. When the tosylate is particularly reactive the thermodynamically more stable methyl ether 3 is isolated. Analogous reactions with DAIB give acetates 4 in high yield. Dialkyl hydrazones give olefinic products (e.g. 7 and 8). (+)-Camphor hydrazone 1k with either MTIB or DAIB gives both camphene 12 (major product) and tricyclene 11 (minor product) suggesting that a carbene pathway accounts for some of the material formed in these oxidations.

  含有吸电子、还原敏感取代基的芳香腙1与MTIB反应，可高效地得到相应的甲苯磺酸酯2。当甲苯磺酸酯具有特别高的反应活性时，则会分离得到热力学上更稳定的方式形成的甲醚3。类似地，与DAIB反应可高效地得到乙酸酯4。二烷基腙则生成烯烃产物（例如7和8）。(+)-樟脑腙1k与MTIB或DAIB反应，会同时生成荻烯12（主要产物）和三环烯11（次要产物），表明在这些氧化反应中，卡宾路径可能用于形成一部分反应产物。
• Ethyl acetate as an acetyl source and solvent for acetylation of alcohols by KOH
  作者：Xiaodan Wang、Huilin Sun、Yao Cheng、Wenfei Yang、Xinmei Wang、Liting Xiong、Yiying Li、Jinhui Wang、Chunli Gan、Chunguang Lin、Huanjun Xu

  DOI：10.1039/d3ra08717d

  日期：——

  efficient, convenient and gram-scalable protocol for the acetylation of alcohols with EtOAc as acetyl source and solvent. Various types of alcohols were successfully transformed into according acetylated products. Good to excellent yields were offered by primary alcohols and low to moderate yields were offered by secondary alcohols.

  KOH 介导的温和、高效、方便且克级规模的醇乙酰化方案，以 EtOAc 作为乙酰基源和溶剂。各类醇已成功转化为相应的乙酰化产品。伯醇提供良好到优异的产率，仲醇提供低到中等的产率。
• 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.
• Cuesta, Pedro J. Martinez de la; Martinez, Eloisa Rus; Sosa, Rafael Palomino, Anales de Quimica, 1995, vol. 91, # 1.2, p. 26 - 31
  作者：Cuesta, Pedro J. Martinez de la、Martinez, Eloisa Rus、Sosa, Rafael Palomino、Perez, Fuensanta I. Palomino

  DOI：——

  日期：——
• Arcus; Schaffer, Journal of the Chemical Society, 1958, p. 2428
  作者：Arcus、Schaffer

  DOI：——

  日期：——