(3,5-dichloro-2-hydroxyphenyl)dimorpholinomethane | 146801-08-3

• 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: (3,5-dichloro-2-hydroxyphenyl)dimorpholinomethane
• 英文别名: 2,4-dichloro-6-(dimorpholinomethyl)phenol；2-[Bis(morpholin-4-yl)methyl]-4,6-dichlorophenol；2,4-dichloro-6-(dimorpholin-4-ylmethyl)phenol
• CAS: 146801-08-3
• 化学式: C₁₅H₂₀Cl₂N₂O₃
• 分子量: 347.241
• InChiKey: YCDUBLUGELEKHI-UHFFFAOYSA-N

物化性质

• 沸点：
  426.7±45.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 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：
  45.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3,5-dichloro-2-hydroxyphenyl)dimorpholinomethane 在 copper(l) iodide 、 甲酸 作用下， 以 乙腈 为溶剂， 反应 0.53h， 生成 5,7-dichloro-2-(cyclohexylidenemethyl)-3-morpholinobenzofuran
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1021721211363
• 作为产物：
  描述：

  吗啉 、 3,5-二氯水杨醛 反应 0.33h， 以96%的产率得到(3,5-dichloro-2-hydroxyphenyl)dimorpholinomethane
  参考文献：
  名称：

  Novel approach to 3,3-dimethyl-4-morpholino-3,4-dihydrocoumarins via hetero-Diels–Alder reaction

  摘要：

  A new four-step synthetic procedure has been developed to prepare 3,3-dimethyl-4-morpholino-3,4-dihydrocoumarins from substituted salicylaldehydes, morpholine, and isobutyraldehyde. It involves aminal formation, deamination, enamine formation, hetero-Diels-Alder reaction, hydrolysis, and oxidation. The aminal formation, subsequent one-pot domino deamination, enamine formation, and hetero-Diels-Alder reaction were achieved in microwave-assisted catalyst-free conditions. The following hydrolysis and oxidation steps, performed conventionally, gave quantitative yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.06.083

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。
• ——
  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.
• ——
  作者：L. Yu. Ukhin

  DOI：10.1023/a:1023923226389

  日期：——

  Fusion of 2-methylindole with morphinals of substituted salicylaldehydes (in a ratio of 1 : 1) afforded 3-[(2-hydroxyaryl)morpholinomethyl]-2-methylindoles as normal products of the Mannich reaction. In some cases, the reactions with an excess of 2-methylindole resulted in unusual condensation accompanied by the replacement of the OH group by the morpholino group to form bis(2-methylindol-3-yl)(2-morpholinoaryl)methanes.
• Novel approach to 3,3-dimethyl-4-morpholino-3,4-dihydrocoumarins via hetero-Diels–Alder reaction
  作者：Divya Mathur、Ashok K. Prasad、T. Stanley Cameron、Amitabh Jha

  DOI：10.1016/j.tet.2014.06.083

  日期：2014.9

  A new four-step synthetic procedure has been developed to prepare 3,3-dimethyl-4-morpholino-3,4-dihydrocoumarins from substituted salicylaldehydes, morpholine, and isobutyraldehyde. It involves aminal formation, deamination, enamine formation, hetero-Diels-Alder reaction, hydrolysis, and oxidation. The aminal formation, subsequent one-pot domino deamination, enamine formation, and hetero-Diels-Alder reaction were achieved in microwave-assisted catalyst-free conditions. The following hydrolysis and oxidation steps, performed conventionally, gave quantitative yields. (C) 2014 Elsevier Ltd. All rights reserved.
• ——
  作者：L. Yu. Ukhin、L. V. Belousova、Zh. I. Orlova、M. S. Korobov、G. S. Borodkin

  DOI：10.1023/a:1021721211363

  日期：——