2-nitromethylquinoline | 5114-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-nitromethylquinoline
• 英文别名: 2-Nitromethyl-chinolin；Quinoline, 2-(nitromethyl)-；2-(nitromethyl)quinoline
• CAS: 5114-78-3
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: SIQRLWJNWZCECZ-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C(Solv: ethanol (64-17-5))
• 沸点：
  336.3±17.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-nitromethylquinoline 在 氯 、 溶剂黄146 作用下， 生成 2-(chloro-nitro-methyl)-quinoline
  参考文献：
  名称：

  Salukaew; Wanag, Zhurnal Obshchei Khimii, 1958, vol. 28, p. 483,485; engl. Ausg. S. 474, 476

  摘要：

  DOI：
• 作为产物：
  描述：

  溶剂黄PS 在 sodium hydroxide 、 硝酸 作用下， 生成 2-nitromethylquinoline
  参考文献：
  名称：

  Salukaew; Wanag, Zhurnal Obshchei Khimii, 1956, vol. 26, p. 2639,2642; engl. Ausg. S. 2943, 2945

  摘要：

  DOI：

文献信息

• ANTI-CANCER AGENTS AND ANDROGEN INHIBITION ACTIVITY COMPOUND
  申请人：Njar Vincent C. O.

  公开号：US20100113600A1

  公开（公告）日：2010-05-06

  A qualitative 3D pharmacophore model (a common feature based model or Catalyst HipHop algorithm) developed from well-known natural product androgen receptor down-regulating agents (ARDAs). The 3D pharmacophore model is used as a template in virtual screening compounds for new ARDAs. ARDA compounds and compounds that strongly inhibit the growth of human prostate LNCaP cells. The compounds may be used in compositions and methods of inhibiting cell proliferation of a cancer and methods of preventing or treating cancer, including prostate cancer.

  使用常见特征基模型或Catalyst HipHop算法从著名的天然产物雄激素受体下调剂（ARDAs）中开发出一种定性的3D药效团模型。该3D药效团模型被用作模板，筛选新的ARDAs化合物。ARDAs化合物和强烈抑制人前列腺LNCaP细胞生长的化合物。这些化合物可用于抑制癌症细胞增殖的组合物和方法，以及预防或治疗癌症，包括前列腺癌的方法。
• Salukaew, Latvijas PSR Zinatnu Akademijas Vestis, 1953, # 11, p. 111,117
  作者：Salukaew

  DOI：——

  日期：——
• Fluorination and chlorination of nitroalkyl groups
  作者：Philip Butler、Bernard T. Golding、Gilles Laval、Hossein Loghmani-Khouzani、Reza Ranjbar-Karimi、Majid M. Sadeghi

  DOI：10.1016/j.tet.2007.08.020

  日期：2007.11

  Heterocycles substituted with a nitromethyl (CH2NO2) or phenyl-nitromethyl (CHPhNO2) group were prepared by reaction of a methyl- or phenylmethyl-substituted heterocycle, respectively, with lithium di-isopropylamide followed by quenching the intermediate carbanion with methyl nitrate. Conversion of CH2NO2 attached to an alkyl or aryl moiety into a dichloronitromethyl (CCl2NO2) group was achieved using N-chlorosuccinimide and 1,8-diazabicyclo[5.4.0] undec-7-ene (DBU) in dichloromethane. Similarly, CH2NO2 attached to an alkyl or aryl group was converted into difluoronitromethyl (CF2NO2) using either 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis( tetrafluoroborate) (Selectfluor (TM)) or N-fluorobenzenesulfonimide with DBU as base and dichloromethane as solvent. Reaction of omega-nitroacetophenone with Selectfluor/DBU in dimethylformamide followed by acidification and distillation gave the parent difluoronitromethane in a useful 'one-pot' procedure. (c) 2007 Elsevier Ltd. All rights reserved.
• Eckstein et al., Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1959, vol. 7, p. 289,290
  作者：Eckstein et al.

  DOI：——

  日期：——
• Sonochemical fluorination of heterocyclic nitro compounds with Selectfluor
  作者：Majid M. Sadeghi、Hossein Loghmani-Khouzani、Reza Ranjbar-Karimi、Philip Butler、Bernard T. Golding

  DOI：10.1016/j.tetlet.2006.03.144

  日期：2006.6