(E)-6-chloro-3-(4-chlorobenzylidene)chroman-4-one | 201424-63-7

• 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: (E)-6-chloro-3-(4-chlorobenzylidene)chroman-4-one
• 英文别名: (3E)-6-chloro-3-[(4-chlorophenyl)methylidene]chromen-4-one
• CAS: 201424-63-7
• 化学式: C₁₆H₁₀Cl₂O₂
• 分子量: 305.16
• InChiKey: QXEWRSADHJPWDV-YRNVUSSQSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  485.6±45.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-6-chloro-3-(4-chlorobenzylidene)chroman-4-one 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 6-chloro-3-(4-chlorobenzylidene)chromanone epoxide
  参考文献：
  名称：

  Mandal, Tapas K.; Sepay, Nayim; Chatterjee, Nachiketa, Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1805 - 1813

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯-4-二氢色原酮 、 4-氯苯甲醛 在 aluminum oxide 作用下， 反应 0.06h， 以89%的产率得到(E)-6-chloro-3-(4-chlorobenzylidene)chroman-4-one
  参考文献：
  名称：

  Facile Condensation of Aromatic Aldehydes with Chroman-4-ones and 1-Thiochroman-4-ones Catalysed by Amberlyst-15 under Microwave Irradiation Condition

  摘要：

  不同的芳香醛和肉桂醛在无溶剂条件下在微波辐射下与4-羟基香豆素和1-硫代-4-羟基香豆素在琥珀酸树脂-15的存在下发生交叉醛醇缩合反应，迅速生成相应的E-3-芳基亚醛和E-3-肉桂醇亚醛衍生物，收率高。这一过程简单、高效且环保。

  DOI：

  10.1155/2011/426560

文献信息

• Facile Condensation of Aromatic Aldehydes with Chroman-4-ones and 1-Thiochroman-4-ones Catalysed by Amberlyst-15 under Microwave Irradiation Condition
  作者：Tapas K. Mandal、Rammohan Pal、Rina Mondal、Asok K. Mallik

  DOI：10.1155/2011/426560

  日期：——

  Different aromatic aldehydes and cinnamaldehyde undergo cross-aldol condensation with chroman-4-ones and1-thiochroman-4-ones in the presence of amberlyst-15 under microwave irradiation in solvent free condition to afford rapidly the correspondingE-3-arylidene andE-3-cinnamylidene derivatives, respectively, in high yield. This process is simple, efficient and environmentally benign.

  不同的芳香醛和肉桂醛在无溶剂条件下在微波辐射下与4-羟基香豆素和1-硫代-4-羟基香豆素在琥珀酸树脂-15的存在下发生交叉醛醇缩合反应，迅速生成相应的E-3-芳基亚醛和E-3-肉桂醇亚醛衍生物，收率高。这一过程简单、高效且环保。
• Stereocontrolled Photodimerization of (E)-3-Benzylidene-4-chromanones in the Crystalline State: The Effect of a Halogen Group on the Chromanone Moiety
  作者：Qi-Yu Zheng、Xue-Ming Cheng、Min Chen、Zhi-Tang Huang

  DOI：10.1055/s-0032-1317511

  日期：——

  in the crystalline state. The stereoselective photoreactions of these compounds in the solid state are examined based on the crystal structures of the reactants and products. All the examples tested undergo photodimerization, except for (E)-3-benzylidene-6-fluorochroman-4-one. The reactants with β-structures give syn-head-to-head (syn-HH) products with high selectivity. Only (E)-6-chloro-3-(4-meth

  摘要 合成了一系列（E）-3-亚苄基-4-苯并二氢吡喃酮衍生物，其被苯并二氢吡喃并并苯并嵌在苯并二氢吡喃酮上以控制分子在结晶态的排列。基于反应物和产物的晶体结构，检查了这些化合物在固态下的立体选择性光反应。除（E）-3-亚苄基-6-氟苯并吡喃-4-酮外，所有测试的实施例均进行了光二聚化。与β结构的反应给予SYN -head -头（SYN -HH）产品具有很高的选择性。仅（ê）-6-氯-3-（4-甲基亚苄基） -苯并二氢吡喃-4-酮采用的α型并给出了一个抗-head -尾（抗-HT）产品。 合成了一系列（E）-3-亚苄基-4-苯并二氢吡喃酮衍生物，其被苯并二氢吡喃并并苯并嵌在苯并二氢吡喃酮上以控制分子在结晶态的排列。基于反应物和产物的晶体结构，检查了这些化合物在固态下的立体选择性光反应。除（E）-3-亚苄基-6-氟苯并吡喃-4-酮外，所有测试的实施例均进行了光二聚化。与β结构的反应给予SYN
• Synthesis and antirhinovirus activity of new 3-benzyl chromene and chroman derivatives
  作者：Cinzia Conti、Nicoletta Desideri

  DOI：10.1016/j.bmc.2009.03.051

  日期：2009.5

  A series of 3-benzyl chromenes and chromans were synthesized and tested in vitro against human rhinovirus (HRV) 1B and 14, two representative serotypes for rhinovirus group B and A, respectively. All the new compounds, with the exception of 3-benzyl-2H-chromene (3a), showed a potent activity against HRV serotype 1B within micro or submicromolar range (IC(50)s from 0.11 to 6.62 mu M). The low cytotoxicity of all the derivatives resulted in compounds with high therapeutic index (TI). On the contrary, HRV 14 infection was only weakly inhibited by the majority of these compounds. The 3-benzylidenechromans 2b and 2c showed the highest anti-HRV 1B activity (IC50 0.12 and 0.11 mu M, respectively) coupled with remarkable TI (625.00 and 340.91, respectively). Mechanism of action studies on (Z)-3-(4-chlorobenzylidene) chroman (2b) suggest that the new compounds behave as capsid binders and interfere with very early stages of HRV 1B replication, similarly to related flavanoids. (C) 2009 Elsevier Ltd. All rights reserved.
• Mandal, Tapas K.; Sepay, Nayim; Chatterjee, Nachiketa, Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1805 - 1813
  作者：Mandal, Tapas K.、Sepay, Nayim、Chatterjee, Nachiketa、Mallik, Asok K.

  DOI：——

  日期：——
• Imidazolium Ionic Liquids as Catalyst for Synthesis of (<i>E</i>)-3-Arylidene(thio)chroman-4-ones under Microwave Irradiation
  作者：Hong-Ya Li、Shu-Na Li、Quan Wang、Shu-Xiang Wang、Bao-Cheng Zhu

  DOI：10.3184/174751912x13466926675198

  日期：2012.11

  Use of imidazolium ionic liquids [Bmim][CF₃COO] and [Bmim]OH as a catalyst for synthesis of 3-arylidene(thio)chroman-4-ones by the condensation of (thio)chroman-4-ones and aromatic aldehydes under microwave irradiation conditions. A series of 3-arylidene(thio)chroman-4-ones were obtained as the only product and considerable increase of yield was founded within short time. The products 3-arylidene(thio)chromanones were assigned the ( E)-configuration based on ¹H NMR spectroscopic data.

  使用咪唑离子液体 [Bmim][CF3COO] 和 [Bmim] OH 作为催化剂，在微波辐照条件下通过（硫代）色曼-4-酮和芳香醛的缩合合成 3-芳基（硫代）色曼-4-酮。一系列 3-芳烷基（硫代）色曼-4-酮是唯一的产物，并且在短时间内产量有了显著提高。根据 1H NMR 光谱数据，产物 3-芳基亚(硫)色满酮的构型为 ( E)。