N-(2-nitrophenyl)butane-1,4-diamine | 66242-22-6

• 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-nitrophenyl)butane-1,4-diamine
• 英文别名: N-(o-nitrophenyl)-1,4-butanediamine；N-(o-Nitrophenyl)tetramethylendiamin；N'-(2-nitrophenyl)butane-1,4-diamine
• CAS: 66242-22-6
• 化学式: C₁₀H₁₅N₃O₂
• mdl: MFCD00622914
• 分子量: 209.248
• InChiKey: LMSPIBZJRMGTOC-UHFFFAOYSA-N

物化性质

• 沸点：
  385.1±27.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-nitrophenyl)butane-1,4-diamine 在 sodium hydroxide 、 ethyl polyphoshate 作用下， 以 氯仿 为溶剂， 反应 30.25h， 生成
  参考文献：
  名称：

  An Efficient Synthesis of 2,3-Dihydro-1H-pyrimido[1,2-a]quinoxaline 6-Oxides

  摘要：

  5 取代的 2,3-二氢-1H-嘧啶并[1,2-a]喹喔啉 6-氧化物 1a-f 是通过 N-酰基-N′-（邻硝基芳基）-1、通过 N-酰基-N′-(邻硝基芳基)-1,4,5,6-四氢嘧啶 2 与多磷酸乙酯 (PPE) 或多磷酸三甲基硅酯 (PPSE) 的环闭合，合成相应的 2-取代 1-(邻硝基芳基)-1,4,5,6-四氢嘧啶 3，然后自发杂环化。 该方法还可用于合成同源的 6-芳基-1,2,3,4-四氢-1,3-二氮杂卓[1,2-a]喹喔啉 7-氧化物（1g）。

  DOI：

  10.1055/s-2002-35980
• 作为产物：
  描述：

  2-硝基苯胺 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 生成 N-(2-nitrophenyl)butane-1,4-diamine
  参考文献：
  名称：

  Selective Small Molecules Blocking HIV-1 Tat and Coactivator PCAF Association

  摘要：

  Development of drug resistance from mutations in the targeted viral proteins leads to continuation of viral production by chronically infected cells, contributing to HIV-mediated immune dysfunction. Targeting a host cell protein essential for viral reproduction, rather than a viral protein, may minimize the viral drug resistance problem as observed with HIV protease inhibitors. We report here the development of a novel class of N1-aryl-propane-1,3-diamine compounds using a structure-based approach that selectively inhibit the activity of the bromodomain of the human transcriptional co-activator PCAF, of which association with the HIV trans-activator Tat is essential for transcription and replication of the integrated HIV provirus.

  DOI：

  10.1021/ja044885g

文献信息

• PERILLO I.; FERNANDEZ B.; LAMDAN S., J. CHEM. SOC. PERKIN TRANS., 1978, 2, NO 15, 2068-2072
  作者：PERILLO I.、 FERNANDEZ B.、 LAMDAN S.

  DOI：——

  日期：——
• Selective Small Molecules Blocking HIV-1 Tat and Coactivator PCAF Association
  作者：Lei Zeng、Jiaming Li、Michaela Muller、Sherry Yan、Shiraz Mujtaba、Chongfeng Pan、Zhiyong Wang、Ming-Ming Zhou

  DOI：10.1021/ja044885g

  日期：2005.3.1

  Development of drug resistance from mutations in the targeted viral proteins leads to continuation of viral production by chronically infected cells, contributing to HIV-mediated immune dysfunction. Targeting a host cell protein essential for viral reproduction, rather than a viral protein, may minimize the viral drug resistance problem as observed with HIV protease inhibitors. We report here the development of a novel class of N1-aryl-propane-1,3-diamine compounds using a structure-based approach that selectively inhibit the activity of the bromodomain of the human transcriptional co-activator PCAF, of which association with the HIV trans-activator Tat is essential for transcription and replication of the integrated HIV provirus.
• An Efficient Synthesis of 2,3-Dihydro-1<i>H-</i>pyrimido[1,2-<i>a</i>]quinoxaline 6-Oxides
  作者：Isabel A. Perillo、María B. García、Liliana R. Orelli、María L. Magri

  DOI：10.1055/s-2002-35980

  日期：——

  5-Substituted 2,3-dihydro-1H-pyrimido[1,2-a]quinoxaline 6-oxides 1a-f were synthesized by ring closure of N-acyl-N′-(o-nitroaryl)-1,3-propanediamines 2 with ethyl polyphosphate (PPE) or trimethylsilyl polyphosphate (PPSE) to the corresponding 2-substituted 1-(o-nitroaryl)-1,4,5,6-tetrahydropyrimidines 3, followed by spontaneous heterocyclization. The method was extended to the synthesis of the homologous 6-aryl-1,2,3,4-tetrahydro-1,3-diazepino[1,2-a]quinoxaline 7-oxide (1g).

  5 取代的 2,3-二氢-1H-嘧啶并[1,2-a]喹喔啉 6-氧化物 1a-f 是通过 N-酰基-N′-（邻硝基芳基）-1、通过 N-酰基-N′-(邻硝基芳基)-1,4,5,6-四氢嘧啶 2 与多磷酸乙酯 (PPE) 或多磷酸三甲基硅酯 (PPSE) 的环闭合，合成相应的 2-取代 1-(邻硝基芳基)-1,4,5,6-四氢嘧啶 3，然后自发杂环化。 该方法还可用于合成同源的 6-芳基-1,2,3,4-四氢-1,3-二氮杂卓[1,2-a]喹喔啉 7-氧化物（1g）。