2-(dimorpholinomethyl)phenol | 127704-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(dimorpholinomethyl)phenol
• 英文别名: Phenol, 2-(di-4-morpholinylmethyl)-；2-(dimorpholin-4-ylmethyl)phenol
• CAS: 127704-26-1
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: FPGCNELEVRCISV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 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：

  2-(dimorpholinomethyl)phenol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成 4-(9-(2-methyl-1-propyl-1H-indol-3-yl)-2,3,4,4a,9,9a-hexahydro-1H-xanthen-4a-yl)morpholine
  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 、 水杨醛 以 乙腈 为溶剂， 反应 0.08h， 以26%的产率得到2-(dimorpholinomethyl)phenol
  参考文献：
  名称：

  通过水杨醛，胺和B2（OH）4的多组分偶合反应合成α-氨基环状硼酸酯

  摘要：

  我们在这里报告的α氨基环状硼酸酯的简明合成通过多组分容易得到水杨醛，胺的耦合，和B 2（OH）4。该方法可以在室温下在乙醇中进行，不需要催化剂或添加剂，并且易于扩大规模。缩醛和连接的硼氧烷是该反应的中间体。

  DOI：

  10.1039/d0gc00346h

文献信息

• Concise synthesis of α-amino cyclic boronates <i>via</i> multicomponent coupling of salicylaldehydes, amines, and B₂(OH)₄
  作者：Wenbo Ming、Xiaocui Liu、Alexandra Friedrich、Johannes Krebs、Yudha P. Budiman、Mingming Huang、Todd B. Marder

  DOI：10.1039/d0gc00346h

  日期：——

  We report here a concise synthesis of α-amino cyclic boronates via multicomponent coupling of readily available salicylaldehydes, amines, and B2(OH)4. The process can be carried out at room temperature in ethanol, does not require catalysts or additives, and is easy to scale up. Aminals and ligated boroxines are intermediates in this reaction.

  我们在这里报告的α氨基环状硼酸酯的简明合成通过多组分容易得到水杨醛，胺的耦合，和B 2（OH）4。该方法可以在室温下在乙醇中进行，不需要催化剂或添加剂，并且易于扩大规模。缩醛和连接的硼氧烷是该反应的中间体。
• Molecular design and QSAR study of low acute toxicity biocides with 4,4′-dimorpholyl-methane core obtained by microwave-assisted synthesis
  作者：Raúl Hernández-Altamirano、Violeta Y. Mena-Cervantes、Sandra Perez-Miranda、Francisco J. Fernández、Cesar Andres Flores-Sandoval、Victor Barba、Hiram I. Beltrán、Luis S. Zamudio-Rivera

  DOI：10.1039/b905153h

  日期：——

  phenol (4c), 2,4-di-tert-butyl-6-(dimorpholinomethyl)-phenol (4d), 4,4′-(pyridin-2-ylmethylene)-dimorpholine (4e), 4,4′-((4-iso-propylphenyl)methylene)-dimorpholine (4f), 4,4′-(naphthalen-1-ylmethylene)-dimorpholine (4g) and 4,4′-(pyren-1-ylmethylene)-dimorpholine (4h). Additionally, single crystal X-ray diffraction analysis for 4b, 4c, 4d and 4e derivatives was accomplished showing interesting geometrical

  微波无溶剂合成醛（1a，2b–h）和吗啉（3）在1 ：2（醛 ： 吗啉）比率产生8种4,4'-二吗啉基甲烷（4a - 4h），通过以下方法对其进行了彻底表征红外光谱，1小时，13 ℃ 和 二维核磁共振，确认类型4的结构。所描述的化合物是双吗啉代--甲烷（4a），2-（二吗啉代甲基）苯酚（4b），4-溴-2-（二吗啉代甲基）苯酚（4c），2,4-二叔丁基-6-（二吗啉代甲基）苯酚（4d），4,4'-（吡啶-2-基亚甲基）-二吗啉（4e），4,4' - （（4-异丙-propylphenyl）亚甲基）-dimorpholine（4f），4,4'-（萘-1-基亚甲基）-二吗啉（4克）和4,4'-（吡喃-1-基亚甲基）-二吗啉（4h）。此外，单晶X射线衍射对4b，4c，4d和4e导数的分析已完成，显示了有趣的几何特征。对获得的4,4'-二吗啉基甲烷进行了两项生物学测试，（i）急性毒性，与发光细菌（fibrio
• 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。
• Komissarov, V. N.; Ukhin, L. Yu., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 12.2, p. 2326 - 2328
  作者：Komissarov, V. N.、Ukhin, L. Yu.

  DOI：——

  日期：——
• 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.