2-氨基-3-氯-5-硝基-1,4-萘醌 | 50711-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-氨基-3-氯-5-硝基-1,4-萘醌
• 英文名称: 2-amino-3-chloro-5-nitro-1,4-naphthoquinone
• 英文别名: 2-Amino-3-chloro-5-nitronaphthalene-1,4-dione
• CAS: 50711-49-4
• 化学式: C₁₀H₅ClN₂O₄
• 分子量: 252.614
• InChiKey: RDAJOEURNCUBIF-UHFFFAOYSA-N

物化性质

• 沸点：
  407.9±45.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氨基-3-氯-5-硝基-1,4-萘醌 在 三甲基乙酰氯 作用下， 以 苯 为溶剂， 以82%的产率得到3,3-Dichloro-2-chloroimino-5-nitro-2,3-dihydro-1,4-naphthoquinone
  参考文献：
  名称：

  Litvin, B. L.; Gubrii, Z. V.; Shermolovich, Yu. G., Russian Journal of Organic Chemistry, 1999, vol. 35, # 3, p. 377 - 383

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氯-5-硝基-1,4-萘醌 在 2,6-二叔丁基吡啶 、 Rink amide resin plug format 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-amino-3-chloro-8-nitro-1,4-naphthoquinone 、 2-氨基-3-氯-5-硝基-1,4-萘醌
  参考文献：
  名称：

  Solid-phase synthesis of 2-amino-3-chloro-5- and 8-nitro-1,4-naphthoquinones: a new and general colorimetric test for resin-bound amines

  摘要：

  Treatment of resin-bound primary or secondary alkyl and arylamines with 2,3-dichloro-5-nitro-1,4-naphthoquinone leads to the rapid formation of intensely colored (red) beads. The resulting 2-amino-3-chloro-5- and 8-nitro-1,4-naphthoquinones can be cleaved rapidly from acid-labile supports in high yields and purities. The reaction is of value as a sensitive and general qualitative test for amino groups on-resin that can be followed by cleavage for characterization and quantification of the chromogen(s) responsible for the color. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.049

文献信息

• Synthesis and amination of 5- and 8-amino derivatives of 2-phenylnaphtho[2,3-d]-1,3-thiazole-4,9-dione
  作者：R. P. Shishkina、N. V. Sergienko

  DOI：10.1007/bf00700175

  日期：1994.12

  5- and 8-Amino-2-phenylnaphtho[2,3-d]-1,3-thiazole-4,9-diones were obtained by treatment of 3,5-diamino-2-chloro- and 2,5 -diamino-3-chloro-1,4-naphthoquinones with sodium sulfide followed by condensation with benzaldehyde. Thermal and photochemical butylamination and CoCl2-promoted arylamination of 5-amino-2-phenylnaphthothiazole-4,9-dione in position 8 was carried out.
• Slesartschuk et al., Zhurnal Organicheskoi Khimii, 1973, vol. 9, p. 2155;engl.Ausg.S.2169
  作者：Slesartschuk et al.

  DOI：——

  日期：——
• SLESARCHUK L. P.; KOLESNIKOV V. T., VISNIK LVIV. POLITEXN. IN-TU, 1979, HO 131, 66-69, 166
  作者：SLESARCHUK L. P.、 KOLESNIKOV V. T.

  DOI：——

  日期：——
• Litvin, B. L.; Gubrii, Z. V.; Shermolovich, Yu. G., Russian Journal of Organic Chemistry, 1999, vol. 35, # 3, p. 377 - 383
  作者：Litvin, B. L.、Gubrii, Z. V.、Shermolovich, Yu. G.、Novikov, V. P.

  DOI：——

  日期：——
• Solid-phase synthesis of 2-amino-3-chloro-5- and 8-nitro-1,4-naphthoquinones: a new and general colorimetric test for resin-bound amines
  作者：Christopher Blackburn

  DOI：10.1016/j.tetlet.2005.01.049

  日期：2005.2

  Treatment of resin-bound primary or secondary alkyl and arylamines with 2,3-dichloro-5-nitro-1,4-naphthoquinone leads to the rapid formation of intensely colored (red) beads. The resulting 2-amino-3-chloro-5- and 8-nitro-1,4-naphthoquinones can be cleaved rapidly from acid-labile supports in high yields and purities. The reaction is of value as a sensitive and general qualitative test for amino groups on-resin that can be followed by cleavage for characterization and quantification of the chromogen(s) responsible for the color. (C) 2005 Elsevier Ltd. All rights reserved.