4-(三氟甲氧基)-靛红 | 959236-54-5

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟靛红系列
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 4-(三氟甲氧基)-靛红
• 中文别名: 4-三氟甲氧基靛红
• 英文名称: trifluoromethoxy-1H-indole-2,3-dione
• 英文别名: 4-(Trifluoromethoxy)indoline-2,3-dione；4-(trifluoromethoxy)-1H-indole-2,3-dione
• CAS: 959236-54-5
• 化学式: C₉H₄F₃NO₃
• 分子量: 231.131
• InChiKey: LBLDKICVIXUAFI-UHFFFAOYSA-N

物化性质

• 密度：
  1.562±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-苄基-3-氨基硫脲 、 4-(三氟甲氧基)-靛红 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以90%的产率得到5-trifluoromethoxy-1H-indole-2,3-dione-3-(N-benzylthiosemicarbazone)
  参考文献：
  名称：

  Three novel compounds of 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone: Synthesis, crystal structures and molecular interactions

  摘要：

  5-Trifluoromethoxy-1H-indole-2,3-dione 3-(N-ethyl/benzylthiosemicarbazone) (2a/2b) and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-(N-ethylthiosemicarbazone) (3a) were synthesized. The structures of the compounds were confirmed by elemental analysis, spectral data and X-ray single crystal diffraction analysis. The morpholin ring which adopts chair conformation and ethylamino group of 3a are disordered over two sets of sites with unequal occupancy. The indole heterocycle is nearly planar and the dihedral angle between the pyrrole and the adjacent phenyl ring is 2.09 degrees (in 2a), 4.61 degrees (in 2b) and 2.16 degrees (in 3a). In all three crystal structures, a strong N-H center dot center dot center dot O hydrogen bond links the flat conjugated H-N-N=C-C=O fragment into a six-membered ring. The molecules 2a, 2b and 3a have potential groups of proton donors (thiosemicarbazone group) available for hydrogen bonding. The structures 2b and 3a consist of isolated molecules, while that of 2a contains dimers formed by C-H center dot center dot center dot O hydrogen bonds. The molecules are linked into three dimensional framework structure by a combination of mainly N-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds and weak C-F center dot center dot center dot pi and pi center dot center dot center dot pi interactions. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.06.039

文献信息

• Three novel compounds of 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone: Synthesis, crystal structures and molecular interactions
  作者：Filiz Betül Kaynak、Süheyla Özbey、Nilgün Karalı

  DOI：10.1016/j.molstruc.2013.06.039

  日期：2013.10

  5-Trifluoromethoxy-1H-indole-2,3-dione 3-(N-ethyl/benzylthiosemicarbazone) (2a/2b) and 5-trifluoromethoxy-1-morpholinomethyl-1H-indole-2,3-dione 3-(N-ethylthiosemicarbazone) (3a) were synthesized. The structures of the compounds were confirmed by elemental analysis, spectral data and X-ray single crystal diffraction analysis. The morpholin ring which adopts chair conformation and ethylamino group of 3a are disordered over two sets of sites with unequal occupancy. The indole heterocycle is nearly planar and the dihedral angle between the pyrrole and the adjacent phenyl ring is 2.09 degrees (in 2a), 4.61 degrees (in 2b) and 2.16 degrees (in 3a). In all three crystal structures, a strong N-H center dot center dot center dot O hydrogen bond links the flat conjugated H-N-N=C-C=O fragment into a six-membered ring. The molecules 2a, 2b and 3a have potential groups of proton donors (thiosemicarbazone group) available for hydrogen bonding. The structures 2b and 3a consist of isolated molecules, while that of 2a contains dimers formed by C-H center dot center dot center dot O hydrogen bonds. The molecules are linked into three dimensional framework structure by a combination of mainly N-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds and weak C-F center dot center dot center dot pi and pi center dot center dot center dot pi interactions. (c) 2013 Elsevier B.V. All rights reserved.