3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one | 1184662-59-6

• 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-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one
• CAS: 1184662-59-6
• 化学式: C₁₈H₁₅NO₆
• 分子量: 341.32
• InChiKey: MRVFVBOKLSHFQN-UHFFFAOYSA-N

物化性质

• 熔点：
  206-207 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  528.9±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one 在 一水合肼 作用下， 以 正丁醇 为溶剂， 反应 8.0h， 以56%的产率得到5-(4-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-1H-pyrazole
  参考文献：
  名称：

  Heterocyclic analogs of combretastatin A-4

  摘要：

  A novel route is proposed for the synthesis of heterocyclic analogs of the naturally occurring combretastatin A-4 based on the reaction of alpha-acetylenic ketones with polyfunctional nucleophiles (hydroxylamine, hydrazine, guanidine). Previously unknown combretastatin A-4 analogs with azole and azine bridges were obtained.

  DOI：

  10.1007/s10593-009-0171-4
• 作为产物：
  描述：

  1-乙炔基-4-硝基苯 、 3,4,5-三甲氧基苯甲酰氯 在 copper(l) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以82%的产率得到3-(4-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one
  参考文献：
  名称：

  Heterocyclic analogs of combretastatin A-4

  摘要：

  A novel route is proposed for the synthesis of heterocyclic analogs of the naturally occurring combretastatin A-4 based on the reaction of alpha-acetylenic ketones with polyfunctional nucleophiles (hydroxylamine, hydrazine, guanidine). Previously unknown combretastatin A-4 analogs with azole and azine bridges were obtained.

  DOI：

  10.1007/s10593-009-0171-4

文献信息

• New transformation of α-acetylenic ketones under the action of 1,2-diaminoethane
  作者：M. P. Davydova、S. F. Vasilevskii、G. A. Tolstikov

  DOI：10.1007/s11172-011-0030-1

  日期：2011.1

  A reaction of 3-aryl-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ones with 1,2-diaminoethane in boiling dioxane leads to 2-aryl-4,5-dihydro-1H-imidazoles and 1-(3,4,5-trimethoxy-phenyl)ethanone.

  3-芳基-1-(3,4,5-三甲氧基苯基)丙-2-炔-1-酮与1,2-二氨基乙烷在沸腾的二氧六环中的反应生成2-芳基-4,5-二氢-1H-咪唑和1-(3,4,5-三甲氧基苯基)乙酮。
• Dissecting Alkynes: Full Cleavage of Polarized C≡C Moiety via Sequential Bis-Michael Addition/Retro-Mannich Cascade
  作者：Saumya Roy、Maria P. Davydova、Runa Pal、Kerry Gilmore、Genrikh A. Tolstikov、Sergei F. Vasilevsky、Igor V. Alabugin

  DOI：10.1021/jo201259j

  日期：2011.9.16

  The reaction of diaryl ketoalkynes with 1,2-diamino ethane leads to e full scission of the triple bond with the formation of acetophenone and imidazoline fragments. In this transformation, one of the alkyne carbons undergoes formal reduction with the formation of three C-H bonds, whereas the other carbon undergoes formal oxidation via the formation of three C-N bonds (one pi and two sigma). Computational analysis confirmed that the key fragmentation step proceeds via a six-membered TS in a concerted manner. Both amines are involved in the fragmentation: the N-H moiety of one amine transfers a proton to the developing negative charge at the enolate oxygen, while the other amine provides direct stereoelectronic assistance to the C-C bond cleavage via a hyperconjugative n(N)->sigma*(C-C) interaction.
• Reaction of α,β-alkynylketones with β-amino alcohols: pseudoephedrine- assisted cleavage of triple bond via formal internal redox process
  作者：Sergei F. Vasilevsky、Maria P. Davydova、Victor I. Mamatuyk、Nadezhda V. Pleshkova、Dmitry S. Fadeev、Igor V. Alabugin

  DOI：10.1016/j.mencom.2015.09.021

  日期：2015.9

  Reaction of 3-aryl-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ones with (+)-pseudoephedrine leads to products of alkyne moiety cleavage, namely, 1-(3,4,5-trimethoxyphenyl)ethanone and N-(1-hydroxy-1-phenylprop-2-yl)-N-methylbenzamides. In the course of the process one of alkyne carbons undergoes a formal reduction to a Me group, whereas the other one is oxidized to a C(O)NRR' moiety.
• Synthesis of new combretastatin A-4 analogues and study of their anti-inflammatory activity
  作者：M. P. Davydova、I. V. Sorokina、T. G. Tolstikova、V. I. Mamatyuk、D. S. Fadeev、S. F. Vasilevsky

  DOI：10.1134/s1068162015010033

  日期：2015.1

  A new approach to the synthesis of natural combretastatin A-4 analogues based on the interaction of a- acetylenic ketones with secondary amines (diethyl amine, pyrrolidine, piperidine, morpholine) was proposed. Previously unknown analogues of combretastatin A-4 containing the 13-aminovinylcarbonyl bridges were synthesized. Anti-inflammatory activity of the obtained compounds was studied on models of exudative inflammation caused by histamine or concanavalin A.
• Heterocyclic analogs of combretastatin A-4
  作者：S. F. Vasilevsky、M. P. Davydova、G. A. Tolstikov

  DOI：10.1007/s10593-009-0171-4

  日期：2008.10

  A novel route is proposed for the synthesis of heterocyclic analogs of the naturally occurring combretastatin A-4 based on the reaction of alpha-acetylenic ketones with polyfunctional nucleophiles (hydroxylamine, hydrazine, guanidine). Previously unknown combretastatin A-4 analogs with azole and azine bridges were obtained.