3-(2-hydroxy-5-nitrophenyl)-3-morpholino-1-phenyl-prop-1-yne | 165402-19-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2-hydroxy-5-nitrophenyl)-3-morpholino-1-phenyl-prop-1-yne
• 英文别名: 2-(1-morpholin-4-yl-3-phenyl-prop-2-ynyl)-4-nitro-phenol；2-(1-morpholino-3-phenylprop-2-yn-1-yl)-4-nitrophenol；2-(1-morpholin-4-ium-4-yl-3-phenylprop-2-ynyl)-4-nitrophenolate
• CAS: 165402-19-7
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: NNUMAVFPEBRJND-UHFFFAOYSA-N

物化性质

• 溶解度：
  12.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-吗啉基-1-环己烯 、 3-(2-hydroxy-5-nitrophenyl)-3-morpholino-1-phenyl-prop-1-yne 反应 0.03h， 以36%的产率得到4a-morpholino-7-nitro-9-phenylethynyl-1,2,3,4,4a,9a-hexahydroxanthene
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1020956614588
• 作为产物：
  描述：

  5-硝基水杨醛 以 异丙醇 为溶剂， 反应 1.05h， 生成 3-(2-hydroxy-5-nitrophenyl)-3-morpholino-1-phenyl-prop-1-yne
  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

• Metal- and Solvent-Free Multicomponent Decarboxylative A³-Coupling for the Synthesis of Propargylamines: Experimental, Computational, and Biological Investigations
  作者：Pavneet Kaur、Bhupinder Kumar、Kamlesh K. Gurjar、Rohtash Kumar、Vinod Kumar、Rakesh Kumar

  DOI：10.1021/acs.joc.9b02806

  日期：2020.2.21

  Decarboxylative A3-coupling of ortho-hydroxybenzaldehydes, secondary amines, and alkynoic acids is performed under catalyst and solvent-free conditions. The developed methodology provided a waste-free method for the synthesis of hydroxylated propargylamines which are versatile precursors for various bioactive heterocyclic scaffolds. The experimental and density functional theory studies revealed that

  邻羟基苯甲醛，仲胺和炔酸的脱羧A3偶联是在无催化剂和无溶剂条件下进行的。所开发的方法为合成羟基化的炔丙基胺提供了一种无浪费的方法，羟基化的炔丙基胺是各种生物活性杂环骨架的通用前体。实验和密度泛函理论研究表明，原位形成的邻醌类中间体（由邻羟基苯甲醛和胺形成）与炔酸进行协同的Eschweiler-Clarke型脱羧反应。评价合成的化合物对MAO-A，MAO-B和AChE的抑制活性，作为治疗各种神经系统疾病的潜在候选药物。
• The use of potassium alkynyltrifluoroborates in Mannich reactions
  作者：George W. Kabalka、Bollu Venkataiah、Gang Dong

  DOI：10.1016/j.tetlet.2003.11.049

  日期：2004.1

  Potassium alkynyltrifluoroborates react with amines and salicylaldehydes in the presence of benzoic acid to generate highly functionalized amines. Ionic liquids such as butylmethylimidazolium tetrafluoroborate (BmimBF(4)) are suitable solvents for the reaction. (C) 2003 Elsevier Ltd. All rights reserved.
• ——
  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.
• 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。