2-(dimorpholinomethyl)-4-nitrophenol | 165402-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(dimorpholinomethyl)-4-nitrophenol
• 英文别名: 5-nitrosalicylaldehyde morpholinal；Phenol, 2-(di-4-morpholinylmethyl)-4-nitro-；2-(dimorpholin-4-ylmethyl)-4-nitrophenol
• CAS: 165402-16-4
• 化学式: C₁₅H₂₁N₃O₅
• 分子量: 323.349
• InChiKey: MDJXYRSEWSVFDK-UHFFFAOYSA-N

物化性质

• 沸点：
  468.4±45.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  91
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(dimorpholinomethyl)-4-nitrophenol 在 水 、 溶剂黄146 作用下， 反应 4.55h， 生成 9-(2-methyl-1H-indol-3-yl)-7-nitro-1,2,3,4,9,9a-hexahydro-4aH-xanthen-4a-ol
  参考文献：
  名称：

  The hit-to-lead optimization of 1,2,3,4,4a,9a-hexahydro-1H-xanthenes as glucocorticoid receptor antagonists

  摘要：

  The structure activity relationship (SAR) study of a 1,2,3,4,4a,9a-hexahydro-1H-xanthene series of selective, human glucocorticoid receptor alpha (hGR alpha) antagonists is reported. Compounds were screened using hydroxyapatite-based GR binding and MMTV-Luc co-transfection reporter gene assays. Four different regions of the scaffold were modified to assess the effects on hGRa antagonism and related potency. Compound 8d exhibits an 8-fold better bioactivity than the original hit 1a, as well as an improved chemical stability, which make it a promising lead for the subsequent optimization. (C) 2014 Ming-Wei Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.03.017
• 作为产物：
  描述：

  吗啉 、 5-硝基水杨醛 以 异丙醇 为溶剂， 反应 1.0h， 以96%的产率得到2-(dimorpholinomethyl)-4-nitrophenol
  参考文献：
  名称：

  合成 1,3-取代炔丙胺和 3H-2-亚乙烯基-3-氨基苯并呋喃衍生物中的胺类

  摘要：

  根据反应条件和起始化合物的性质，芳香羟基醛的胺与末端乙炔反应生成 1,3-取代炔丙胺或 3H-2-亚乙烯基-3-氨基苯并呋喃衍生物，其结构为通过 X 射线衍射确定。

  DOI：

  10.1007/bf01169718

文献信息

• Synthesis of hexa-, tetra-, and dihydroxanthene derivatives from salicylaldehyde aminals
  作者：L. Yu. Ukhin、V. A. Kharlanov、E. V. Solomovich、O. V. Shishkin

  DOI：10.1007/bf02494643

  日期：1999.5

  Salicylaldehyde aminals react with cyclohexanone upon heating to form tetrahydroxanthene derivatives. The structure of one of these derivatives,viz., 5,7-dichloro-4a-morpholino-1,2,3,4-tetrahydro-4aH-xanthene, was established by X-ray diffraction analysis. The scheme of the reaction was suggested, which involves cycloaddition of intermediateo-methylenequinone (from aminal) and enamine (from cyclohexanone)

  水杨醛缩醛胺在加热时与环己酮反应形成四氢氧杂蒽衍生物。这些衍生物之一的结构，即 5,7-dichloro-4a-morpholino-1,2,3,4-tetrahydro-4aH-xanthene，通过 X 射线衍射分析确定。建议的反应方案包括中间体-亚甲基醌（来自胺醛）和烯胺（来自环己酮）的环加成。水杨醛缩醛胺与由环己酮形成的烯胺反应可以依次得到六氢氧杂蒽、四氢氧杂蒽和二氢氧杂蒽的衍生物。开发了合成这些化合物的程序。 N-取代的 4a-氨基-7-硝基-1,2,3,4-四氢-4aH-呫吨也通过二烷基铵 2-甲酰基-4-硝基苯氧化物与上述烯胺。
• Aminals in the synthesis of 1,3-substituted propargylamines and 3H-2-vinylidene-3-aminobenzofuran derivatives
  作者：L. Yu. Ukhin、V. N. Komissarov、S. V. Lindeman、V. N. Khrustalev、Yu. T. Struchkov

  DOI：10.1007/bf01169718

  日期：1994.3

  Aminals of aromatico-hydroxyaldehydes react when heated with terminal acetylenes to form, depending on the reaction conditions and the nature of the starting compounds, 1,3-substituted propargylamines or 3H-2-vinylidene-3-aminobenzofuran derivatives, the structures of which were established by X-ray diffraction.

  根据反应条件和起始化合物的性质，芳香羟基醛的胺与末端乙炔反应生成 1,3-取代炔丙胺或 3H-2-亚乙烯基-3-氨基苯并呋喃衍生物，其结构为通过 X 射线衍射确定。
• Synthesis of (2-hydroxy-5-nitrophenyl)di[1-(2-hydroxynaphthyl)]methane and 12-[1-(2-hydroxynaphthyl)]-10-nitro-12H-benzo[α]xanthene from of 5-nitrosalicylaldehyde derivatives and β-naphthol
  作者：L. Yu. Ukhin、O. V. Shishkin

  DOI：10.1007/bf02495928

  日期：1997.7

  The reaction of the morpholinal or anil of 5-nitrosalicylaldehyde with β-naphthol yielded (2-hydroxy-5-nitrophenyl)di[1-(2-hydroxynaphthyl)]methane. Condensation of the latter compound in boiling nitromethane gave 12-[1-(2-hydroxynaphthyl)]-10-nitro-12H-benzo[α]xanthene.

  5-硝基水杨醛的吗啉醛或苯胺与β-萘酚反应生成(2-羟基-5-硝基苯基)二[1-(2-羟基萘基)]甲烷。后一种化合物在沸腾的硝基甲烷中缩合得到 12-[1-(2-羟基萘基)]-10-硝基-12H-苯并[α]呫吨。
• ——
  作者：L. Yu. Ukhin、L. V. Belousova、Zh. I. Orlova、M. S. Korobov、G. S. Borodkin

  DOI：10.1023/a:1021721211363

  日期：——
• ——
  作者：L. Yu. Ukhin、L. V. Belousova、Zh. I. Orlova、S. V. Shishkina、O. V. Shishkin

  DOI：10.1023/a:1020956614588

  日期：——

  The reactions of aminals, the Mannich bases, and azomethines derived from substituted salicylaldehydes were studied. Derivatives of tetrahydrocyclopenta[b]- and hexahydro-cyclohepta[b]chromenes and substituted 2,2'-spirobichromenes were prepared from aminals, and substituted hexahydroxanthenes were synthesized from the Mannich bases. Azomethine derivatives of 5-nitrosalicylaldehyde and aliphatic amines react with cyclohexanone to form 4a-amino-7-nitro-2,3,4,4a-tetrahydro-1H-xanthenes. 4a-Morpholino-7-nitro-9-phenylethynyl-1,2,3,4,9,9a-hexahydroxanthene was studied by X-ray diffraction analysis.