N-2,4-Dinitrophenyl-L-prolinol | 7754-77-0

• 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: N-2,4-Dinitrophenyl-L-prolinol
• 英文别名: [(2S)-1-(2,4-dinitrophenyl)pyrrolidin-2-yl]methanol
• CAS: 7754-77-0
• 化学式: C₁₁H₁₃N₃O₅
• 分子量: 267.241
• InChiKey: DUBFMJZROXYGFD-VIFPVBQESA-N

物化性质

• 沸点：
  472.5±35.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-2,4-Dinitrophenyl-L-prolinol 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction: SAR studies on conformationally constrained analogues of Linezolid

  摘要：

  A series of conformationally constrained analogues of Linezolid were synthesised by employing a tandem SN2 and SNAr reaction as the key step and tested for antibacterial activity. While the hexahydroazolo-quinoxaline compounds were inactive, the tetrahydroazolo-benzothiazine compounds exhibited interesting antibacterial activity. The introduction of fluorine in the aromatic ring further made the compounds more potent in acetamide compounds resulting in an interesting analogue 32. However, the introduction of fluorine (analogue 34) on the already potent non-fluorine thiocarbamate 21 did not have any influence on the activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.071
• 作为产物：
  描述：

  (S)-N-acetylprolinol 在 盐酸 、 氢氧化钾 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.25h， 生成 N-2,4-Dinitrophenyl-L-prolinol
  参考文献：
  名称：

  某些烷基芳基硝基化合物中 O→N 型微笑重排的观察

  摘要：

  报道了一些具有NH 2 基团作为亲核试剂和氧作为离去基团的烷基芳基硝基化合物的Smiles重排。

  DOI：

  10.1055/s-2002-35227

文献信息

• An unexpected ring contraction of two nitroaryl pro-drugs: conversion of N-(nitroaryl)-3-chloropiperidine derivatives into N-(nitroaryl)-2-chloromethylpyrrolidines
  作者：Philip J. Burke、Lai Chun Wong、William Clegg、Ross W. Harrington、Terence C. Jenkins、Richard J. Knox、Ian T. Meikle、Stephen P. Stanforth

  DOI：10.1016/j.tetlet.2010.05.095

  日期：2010.7

  Treatment of the N-nitroaryl-3-hydroxypiperidine derivatives 12 and 13 with thionyl chloride afforded the corresponding N-aryl-2-chloromethylpyrrolidines 5 and 15 via a ring-contraction process involving an intermediate aziridinium ion.

  用亚硫酰氯处理N-硝基芳基-3-羟基哌啶衍生物12和13，通过涉及中间叠氮鎓离子的环收缩法得到相应的N-芳基-2-氯甲基吡咯烷5和15。
• Observation of O→N Type Smiles Rearrangement in Certain Alkyl Aryl Nitro Compounds
  作者：Natesan Selvakumar、Deekonda Srinivas、Azagarsamy Malar Azhagan

  DOI：10.1055/s-2002-35227

  日期：——

  Smiles rearrangements on some alkyl aryl nitro compounds having NH 2 group as the nucleophile and oxygen as the leaving group are reported.

  报道了一些具有NH 2 基团作为亲核试剂和氧作为离去基团的烷基芳基硝基化合物的Smiles重排。
• Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction: SAR studies on conformationally constrained analogues of Linezolid
  作者：N. Selvakumar、B. Yadi Reddy、G. Sunil Kumar、Manoj Kumar Khera、D. Srinivas、M. Sitaram Kumar、Jagattaran Das、Javed Iqbal、Sanjay Trehan

  DOI：10.1016/j.bmcl.2006.05.071

  日期：2006.8

  A series of conformationally constrained analogues of Linezolid were synthesised by employing a tandem SN2 and SNAr reaction as the key step and tested for antibacterial activity. While the hexahydroazolo-quinoxaline compounds were inactive, the tetrahydroazolo-benzothiazine compounds exhibited interesting antibacterial activity. The introduction of fluorine in the aromatic ring further made the compounds more potent in acetamide compounds resulting in an interesting analogue 32. However, the introduction of fluorine (analogue 34) on the already potent non-fluorine thiocarbamate 21 did not have any influence on the activity. (c) 2006 Elsevier Ltd. All rights reserved.