ethyl 2-nitro-5-oxo-5-phenylpentanoate | 91958-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-nitro-5-oxo-5-phenylpentanoate
• 英文别名: ethyl 2-nitro-5-phenyl-5-oxopentanoate；2-nitro-5-oxo-5-phenyl-valeric acid ethyl ester；2-Nitro-5-oxo-5-phenyl-valeriansaeure-aethylester；2-Nitro-4-benzoyl-buttersaeure-aethylester
• CAS: 91958-55-3
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: UXHBMTMQDAERQC-UHFFFAOYSA-N

物化性质

• 熔点：
  18-19 °C
• 沸点：
  182-182.5 °C(Press: 2 Torr)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-nitro-5-oxo-5-phenylpentanoate 在 palladium on activated charcoal 氢气 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 10.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 ethyl 5-phenylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides

  摘要：

  Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding gamma-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a hetero-Cope rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00094-6
• 作为产物：
  描述：

  硝基乙酸乙酯 、 吖啶橙 以 甲苯 为溶剂， 以100%的产率得到ethyl 2-nitro-5-oxo-5-phenylpentanoate
  参考文献：
  名称：

  Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides

  摘要：

  Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding gamma-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a hetero-Cope rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00094-6

文献信息

• Base-free conjugate addition of aliphatic nitro compounds to enones in BmimNTf2: a recyclable synthesis of γ-nitro ketones
  作者：Raffaella Mancuso、Alessandro Palmieri、Roberto Ballini、Bartolo Gabriele

  DOI：10.1016/j.tet.2012.05.024

  日期：2012.7

  A base-free, recyclable approach for the conjugate addition of aliphatic nitro compounds to enones to give γ-nitro ketones is presented. Reactions are carried out in an ionic liquid with a basic anionic moiety, such as BmimNTf2, as the solvent, under mild conditions (25 °C for 24 h). The IL medium could be recycled several times without any appreciable loss of activity, after a simple extraction procedure

  提出了一种无碱，可回收的方法，用于将脂肪族硝基化合物共轭加成至烯酮以生成γ-硝基酮。反应在温和的条件下（25°C进行24小时）在具有碱性阴离子部分（例如BmimNTf 2）作为溶剂的离子液体中进行。在分离反应产物的简单提取程序后，IL培养基可以循环使用几次，而活性没有任何明显的损失。
• Dornow et al., Justus Liebigs Annalen der Chemie, 1954, vol. 588, p. 62,67
  作者：Dornow et al.

  DOI：——

  日期：——
• Synthesis of Ethyl 5-Phenyl-6-Oxa-1-Azabicyclo[3.1.0]hexane-2-carboxylate Derivatives and Evaluation of Their Antimalarial Activities
  作者：Nongpanga Ningsanont、David St. C. Black、Rachada Chanphen、Yodhathai Thebtaranonth

  DOI：10.1021/jm020452h

  日期：2003.6.1

  Derivatives of ethyl 5-phenyl-6-oxa-1-azabicyclo[3.1.0]hexane-2-carboxylate (14-20), with side chains varying from three to five carbon atoms and bearing various substituents, have been prepared from ethyl 2-phenyl-1-pyrroline-5-carboxylate (12). Their in vitro activity against P. falciparum (K1 strain) and antimycobacterium and also their cytotoxic activity against Vero cell have been evaluated.
• Addition of esters of nitroacetic acid to ?,?-unsaturated ketones
  作者：I. S. Ivanova、N. N. Bulatova、S. S. Novikov

  DOI：10.1007/bf00905321

  日期：1962.5