3-(3',4',5'-trimethoxybenzylidene)chroman-4-one | 869737-07-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: 3-(3',4',5'-trimethoxybenzylidene)chroman-4-one
• 英文别名: (E)-3-(3,4,5-trimethoxybenzylidene)chroman-4-one；(3E)-3-[(3,4,5-trimethoxyphenyl)methylidene]chromen-4-one
• CAS: 869737-07-5
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: HXKRMVAESHQPKO-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3',4',5'-trimethoxybenzylidene)chroman-4-one 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 、 丙酮 为溶剂， 以71%的产率得到3'-(3,4,5-trimethoxyphenyl)spiro[2H-chromene-3,2'-oxirane]-4-one
  参考文献：
  名称：

  Hammam, Abou El-Fotooh G.; Fahmy; Amr, Abdel-Galil E., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 8, p. 1985 - 1993

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氢苯并吡喃-4-酮 、 3,4,5-三甲氧基苯甲醛 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以95%的产率得到3-(3',4',5'-trimethoxybenzylidene)chroman-4-one
  参考文献：
  名称：

  trans-7-Aryl-6H-6a,7-dihydro[1]benzopyrano[3,4-c][1,5]benzothiazepines的一锅法合成

  摘要：

  苯硫醇与 3-亚芳基烯色满-4-酮的缩合反应作为合成子合成一系列新反式-7-芳基-6H-6a,7-二氢[1‖苯并吡喃‖3,4-c 的绿色化学方法][1,5]苯并硫氮杂可能具有潜在的生物活性进行了描述。

  DOI：

  10.3987/com-05-10485

文献信息

• Facile synthesis of spiro chromanone-tetrahydrothiophenes with three contiguous stereocenters via sulfa-Michael/aldol cascade reactions
  作者：Ya-Jian Hu、Xiao-Bing Wang、Su-Yi Li、Sai-Sai Xie、Kelvin D.G. Wang、Ling-Yi Kong

  DOI：10.1016/j.tetlet.2014.11.026

  日期：2015.1

  A novel sulfa-Michael/aldol cascade reaction of (E)-3-arylidenechroman-4-ones with 1,4-dithiane-2,5-diol has been developed. This method provides a new practical and facile approach to 4′-hydroxy-2′-aryl-4′,5′-dihydro-2′H-spiro[chroman-3,3′-thiophen]-4-ones with three contiguous stereocenters in high yields. The transformation is atom-economic with good to excellent diastereoselectivities.

  （E）-3-芳基苯并二氢吡喃-4-酮与1，4-二噻吩-2，5-二醇的新型磺胺-迈克尔/羟醛级联反应已得到开发。此方法提供了一种新的实用的和容易的方法来4'-羟基-2'-芳基-4'，5'-二氢-2' ħ -螺[色满-3,3'-噻吩] -4-酮用三个连续高产量的立体中心。该转化是原子经济的，具有良好的至优异的非对映选择性。
• One-pot Synthesis of trans-7-Aryl-6H-6a,7-dihydro[1]benzopyrano[3,4-c][1,5]benzothiazepines
  作者：Edward R. Biehl、Ramadas Sathunuru、Benjamin Koh、Hongming Zhang、Ed Biehl

  DOI：10.3987/com-05-10485

  日期：——

  Green chemical approaches for the condensation reaction of benzenethiols and 3-arylidenenchroman-4-ones as synthons for the synthesis of a series of newtrans-7-aryl-6H-6a,7-dihydro[1‖benzo pyrano‖3,4-c][1,5]benzo-thiazepines which may possess potential biological activity are described.

  苯硫醇与 3-亚芳基烯色满-4-酮的缩合反应作为合成子合成一系列新反式-7-芳基-6H-6a,7-二氢[1‖苯并吡喃‖3,4-c 的绿色化学方法][1,5]苯并硫氮杂可能具有潜在的生物活性进行了描述。
• Homoisoflavonoids: Natural Scaffolds with Potent and Selective Monoamine Oxidase-B Inhibition Properties
  作者：Nicoletta Desideri、Adriana Bolasco、Rossella Fioravanti、Luca Proietti Monaco、Francisco Orallo、Matilde Yáñez、Francesco Ortuso、Stefano Alcaro

  DOI：10.1021/jm1013709

  日期：2011.4.14

  A series of homoisoflavonoids [(E)-3-benzylidenechroman-4-ones la-w, 3-benzyl-4H-chromen-4-ones 2a-g, and 3-benzylchroman-4-ones 3a-e] have been synthesized and tested in vitro as inhibitors of human monoamine oxidase isoforms A and B (hMAO-A and hMAO-B). Most of the compounds were found to be potent and selective MAO-B inhibitors. In general, the (E)-3-benzylidenechroman-4-ones la-w showed activities in the nano- or micromolar range coupled with high selectivity against hMAO-B. The reduction of the exocyclic double bond results in compounds 3a-e selective against isoform B and active in the micromolar range. In contrast, the endocyclic migration of the double bond (compounds 2a-g) generally produces the loss of the inhibitory activity or a marked reduction in potency. (E)-3-(4-(Dimethylamino)benzylidene)chroman-4-one (1l) and (E)-5,7-dihydroxy-3-(4-hydroxybenzylidene)chroman-4-one (1h) were the most interesting compounds of the entire series of inhibitors, showing hMAO-B affinity better than the selective inhibitor selegiline. Molecular modeling studies have been carried out to explain the selectivity of the most active homoisoflavonoids 1h and 1l.
• Hammam, Abou El-Fotooh G.; Fahmy; Amr, Abdel-Galil E., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 8, p. 1985 - 1993
  作者：Hammam, Abou El-Fotooh G.、Fahmy、Amr, Abdel-Galil E.、Mohamed, Ashraf M.

  DOI：——

  日期：——