4-hydroxy-3-methyl-6-nitro-2-phenylindole

• 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
• 英文名称: 4-hydroxy-3-methyl-6-nitro-2-phenylindole
• 英文别名: 3-methyl-6-nitro-2-phenyl-1H-indol-4-ol
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: FCHBAUUTKDXNDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-methyl-6-nitro-2-phenylindole 、 硫酸二甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到4-methoxy-1,3-dimethyl-6-nitro-2-phenyl-1H-indole
  参考文献：
  名称：

  Synthesis, antifungal activity and QSAR study of 2-arylhydroxynitroindoles

  摘要：

  A series of 2-arylhydroxynitroindoles were prepared and tested for antifungal activity in vitro. The preliminary bioassays indicated that some compounds are comparable to the commercial fungicide (triadimefon). To further explore the structure-activity relationships, the data set of the seventeen structures and their quantitative values of antifungal activities were used for QSAR modeling. Based on the obtained QSAR models four new chemical compounds were designed, synthesized and tested in fungicidal assays. Reasonable correspondence between the experimental and predicted values of antifungal activity was observed. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.008
• 作为产物：
  描述：

  (NE)-N-(1-苯基亚丙基)羟胺 在 盐酸 、 iron(III) chloride hexahydrate 、 potassium carbonate 、 甲烷 、 一水合肼 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 乙醇 、 水 为溶剂， 反应 2.0h， 生成 4-hydroxy-3-methyl-6-nitro-2-phenylindole
  参考文献：
  名称：

  Synthesis, antifungal activity and QSAR study of 2-arylhydroxynitroindoles

  摘要：

  A series of 2-arylhydroxynitroindoles were prepared and tested for antifungal activity in vitro. The preliminary bioassays indicated that some compounds are comparable to the commercial fungicide (triadimefon). To further explore the structure-activity relationships, the data set of the seventeen structures and their quantitative values of antifungal activities were used for QSAR modeling. Based on the obtained QSAR models four new chemical compounds were designed, synthesized and tested in fungicidal assays. Reasonable correspondence between the experimental and predicted values of antifungal activity was observed. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.008

文献信息

• Intramolecular cyclization of O-(3,5-dinitrophenyl) and O-(3-amino-5-nitrophenyl) ketoximes, products of transformations of 1,3,5-trinitrobenzene. The synthesis of nitrobenzo[b]furans and 4-hydroxynitroindoles
  作者：S. S. Vorob’ev、M. D. Dutov、I. A. Vatsadze、E. P. Petrosyan、V. V. Kachala、Yu. A. Strelenko、S. A. Shevelev

  DOI：10.1007/s11172-007-0153-6

  日期：2007.5

  O-(3,5-Dinitrophenyl) ketoximes obtained in the reactions of ketoximes with 1,3,5-trinitrobenzene undergo acid-catalyzed cyclization into 2-substituted or 2,3-disubstituted 4,6-dinitrobenzo[b]furans. In analogous cyclization, products of selective reduction of a nitro group in O-(3,5-dinitrophenyl) ketoximes unexpectedly yield, along with 6-amino-4-nitrobenzofurans, 4-hydroxy-6-nitroindoles. The 4-NO2 group is displaced from 4,6-dinitrobenzo[b]furans in reactions with thiols in the presence of K2CO3. Conditions for nitration and sulfochlorination of 4,6-dinitrobenzo[b]furans in position 3 were found. Condensation of a 2-methyl derivative with dimethylformamide acetal was accomplished.

  在酮肟与 1,3,5-三硝基苯反应中得到的 O-(3,5-二硝基苯基)酮肟在酸催化下环化成 2-取代或 2,3-二取代的 4,6-二硝基苯并[b]呋喃。在类似的环化过程中，选择性还原 O-(3,5-二硝基苯基)酮肟中的硝基的产物意外地与 6-氨基-4-硝基苯并呋喃一起生成了 4-羟基-6-硝基吲哚。在 K2CO3 的存在下，4,6-二硝基苯并[b]呋喃中的 4-NO2 基团与硫醇发生反应而发生位移。找到了 4,6-二硝基苯并[b]呋喃第 3 位硝化和磺酰氯化的条件。完成了 2-甲基衍生物与二甲基甲酰胺缩醛的缩合。
• Unexpected formation of 4-hydroxy-6-nitroindoles in the intramolecular cyclization of O-(3-amino-5-nitrophenyl)ketoximes
  作者：Sergei S. Vorob’ev、Mikhail D. Dutov、Irina A. Vatsadze、Vadim V. Kachala、Yuri A. Strelenko、Andrei V. Sedov、Svyatoslav A. Shevelev

  DOI：10.1016/j.mencom.2007.03.026

  日期：2007.3

  The acid-catalysed cyclization of O-(3-amino-5-nitrophenyl)ketoximes unexpectedly gives, along with 6-amino-4-nitrobenzo-furans, 4-hydroxy-6-nitroindoles (in a 1: 1 ratio).
• Synthesis, antifungal activity and QSAR study of 2-arylhydroxynitroindoles
  作者：Galina V. Kokurkina、Mikhail D. Dutov、Svyatoslav A. Shevelev、Sergey V. Popkov、Alexey V. Zakharov、Vladimir V. Poroikov

  DOI：10.1016/j.ejmech.2011.07.008

  日期：2011.9

  A series of 2-arylhydroxynitroindoles were prepared and tested for antifungal activity in vitro. The preliminary bioassays indicated that some compounds are comparable to the commercial fungicide (triadimefon). To further explore the structure-activity relationships, the data set of the seventeen structures and their quantitative values of antifungal activities were used for QSAR modeling. Based on the obtained QSAR models four new chemical compounds were designed, synthesized and tested in fungicidal assays. Reasonable correspondence between the experimental and predicted values of antifungal activity was observed. (C) 2011 Elsevier Masson SAS. All rights reserved.