(E)-1-phenyl-5-(3,4,5-trimethoxyphenyl)pent-4-ene-1,3-dione | 1449290-07-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E)-1-phenyl-5-(3,4,5-trimethoxyphenyl)pent-4-ene-1,3-dione
• CAS: 1449290-07-6
• 化学式: C₂₀H₂₀O₅
• 分子量: 340.376
• InChiKey: NEHOLZNUZKOXRR-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-5-(3,4,5-trimethoxyphenyl)pent-4-ene-1,3-dione 在 一水合肼 、 溶剂黄146 作用下， 以75%的产率得到(E)-5-phenyl-3-(3,4,5-trimethoxystyryl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

  摘要：

  A click-type entry into shortened curcuminoids of the diarylpentanoid type has been developed. The reaction is ideally suited to generate non-symmetrical analogues of curcumin, a class of natural products difficult to access but of growing biomedical relevance and special mechanistic interest to investigate the unique binding mode of curcumin to tubulin. Investigation of a series of click diarylpentane curcuminoids and their pyrazole adducts in various cellular tubulin functional assays validated this class of compounds as a novel type of anti-mitotic agents, evidencing structure-activity relationships, and identifying the pyrazole adduct 4k as a promising lead. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.053
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 1-苯基-1,3-丁二酮 在 boron trioxide 、 硼酸三甲酯 、 正丁胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到(E)-1-phenyl-5-(3,4,5-trimethoxyphenyl)pent-4-ene-1,3-dione
  参考文献：
  名称：

  Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids

  摘要：

  A click-type entry into shortened curcuminoids of the diarylpentanoid type has been developed. The reaction is ideally suited to generate non-symmetrical analogues of curcumin, a class of natural products difficult to access but of growing biomedical relevance and special mechanistic interest to investigate the unique binding mode of curcumin to tubulin. Investigation of a series of click diarylpentane curcuminoids and their pyrazole adducts in various cellular tubulin functional assays validated this class of compounds as a novel type of anti-mitotic agents, evidencing structure-activity relationships, and identifying the pyrazole adduct 4k as a promising lead. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.053

文献信息

• Highly diastereoselective annulation of 2-substituted 3-nitro-2<i>H</i>-chromenes with hemicurcuminoids and curcuminoids <i>via</i> a double and triple Michael reaction cascade
  作者：Nikolay S. Zimnitskiy、Alexey Yu. Barkov、Ivan A. Kochnev、Igor B. Kutyashev、Vladislav Yu. Korotaev、Vyacheslav Ya. Sosnovskikh

  DOI：10.1039/d2nj02019j

  日期：——

  72 h in the presence of Cs2CO3 proceeds by way of a triple Michael/Michael/oxa-Michael cascade leading to 3,6-diaryl-6a-nitro-2,3,5,6a,7,12b-hexahydro-1H,6H-chromeno[6,5-c]chromen-1-ones in 71–97% yields. 2-Phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes under the analogous conditions react with enediones to form 2-(2-phenyl-2-(trifluoromethyl)-2H-chromen-4-yl)-1,5-diarylpent-4-ene-1,3-diones as a result

  K 2 CO 3催化的 ( E )-1,5-二芳基-和 1-烷基-5-芳基戊-4-烯-1,3-二酮与 2-三氟甲基-和 2-苯基-取代的双迈克尔加成3-nitro-2 H -chromenes 在二氯甲烷中在室温下放置 48 小时，生成 10-aroyl(acyl)-7-aryl-6a-nitro-6,6a,7,8,10,10a-hexahydro-9 H -苯并[ c ]chromen-9-ones 以 75–98% 的产率作为单独的非对映异构体在 C-6、C-6a 和 C-7 原子和 H-9b 原子上相对于稠合三环体系具有顺式排列的取代基. 在 Cs 2 CO 3存在下，类姜黄素在氯仿中回流 72 小时的类似立体选择性过程通过三重 Michael/Michael/oxa-Michael 级联产生 3,6-diaryl-6a-nitro-2,3,5,6a,7,12b-hexahydro-1