3-benzylidene-2-phenyl-2,3-dihydro-4H-chromen-4-one | 22084-15-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3-benzylidene-2-phenyl-2,3-dihydro-4H-chromen-4-one
• 英文别名: 3-benzylideneflavanone；Benzalflavanon；3-benzylidene-2-phenylchromen-4-one
• CAS: 22084-15-7
• 化学式: C₂₂H₁₆O₂
• 分子量: 312.368
• InChiKey: HLGKTNUAJOFUMY-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C(Solv: ethanol (64-17-5))
• 沸点：
  505.0±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  重氮甲烷 、 3-benzylidene-2-phenyl-2,3-dihydro-4H-chromen-4-one 以 丙酮 为溶剂， 生成 2'-phenylchromanone-3'-spiro-3,4-phenyl-1-pyrazoline
  参考文献：
  名称：

  螺黄酮衍生物的细胞毒作用、它们与人血清白蛋白 (HSA) 的结合能力及其合成机制的 DFT 研究

  摘要：

  摘要 本文研究了 9 种具有螺吡唑啉结构的化合物的细胞毒作用，并确定了重氮甲烷与选定的亚苄基黄烷酮之间的反应机制、它们的亲脂性以及它们与人血清白蛋白的结合能力。对两种人白血病细胞系（HL-60 和 NALM-6）和黑色素瘤 WM-115 细胞以及正常人脐静脉内皮细胞 (HUVEC) 确定了细胞毒性作用。化合物 B7 表现出最高的细胞毒性：发现它对所有三种癌细胞系的 IC50 均小于 10 μM，对正常细胞 (HUVEC) 的敏感性低 5 至 12 倍。所有化合物在人血清白蛋白结合中表现出相当的亲和能（从 -8.1 到 -8.6 kcal mol-1），但它们的结合位点因取代基而异。

  DOI：

  10.1016/j.molstruc.2017.02.037
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 苯甲醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 96.0h， 生成 3-benzylidene-2-phenyl-2,3-dihydro-4H-chromen-4-one 、 苯甲酸 、 黄烷酮
  参考文献：
  名称：

  Study on catalytic property of NaOH-cationic surfactant solutions for efficient, green and selective synthesis of flavanone

  摘要：

  The catalytic activity of aqueous NaOH-quaternary ammonium surfactant (NaOH-QAS) solutions was studied for efficient and selective synthesis of flavanone by cross aldol reaction of benzaldehyde and o-hydroxy acetophenone (as model reaction) under ambient condition (at 30 degrees C). The surfactant's nature (alkyl chain length and head group size) and concentration influence the reaction in NaOH-QAS micellar solutions. The NaOH-QAS systems, with surfactant concentration below critical micelle concentration (CMC), showed high activity giving high conversion and flavanone selectivity. This result was interpreted as substrate induced micellization and favorable interactions of surfactant molecules with reactants and intermediates. The reduction in conversion and selectivity of flavanone was observed with NaOH-QAS solutions having surfactant concentration at CMC or above CMC, which was due to strong solubilization of o-hydroxy acetophenone and intermediates in the micelles. The highest conversion (92% in 24 h) and selectivity of flavanone (98%) were obtained with NaOH-cetylpyridinium chloride (NaOH-C(16)PQAS) system at surfactant concentration below CMC. The -OH group present in o-hydroxy acetophenone was observed to be responsible for its less reactivity in the aldol reaction. The reusability of NaOH-cationic surfactant solution was examined for three reaction cycles. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molliq.2015.02.017

文献信息

• Synthesis of 2-alkyl-1-aryl-1,2-dihydrochromeno[2,3-c]pyrrole-3,9-dione derivatives
  作者：R. N. Vydzhak、S. Ya. Panchishin

  DOI：10.1134/s1070363208120165

  日期：2008.12

  A preparative procedure for the synthesis of 2-alkyl-1-aryl-1,2-dihydrochromeno[2,3-c]pyrrole-3,9-diones from methyl 4-(o-hydroxyphenyl)-2,4-dioxobutanoate, aromatic aldehyde, and aliphatic amine is described.
• Study on catalytic property of NaOH-cationic surfactant solutions for efficient, green and selective synthesis of flavanone
  作者：Manu Vashishtha、Manish Mishra、Dinesh O. Shah

  DOI：10.1016/j.molliq.2015.02.017

  日期：2015.10

  The catalytic activity of aqueous NaOH-quaternary ammonium surfactant (NaOH-QAS) solutions was studied for efficient and selective synthesis of flavanone by cross aldol reaction of benzaldehyde and o-hydroxy acetophenone (as model reaction) under ambient condition (at 30 degrees C). The surfactant's nature (alkyl chain length and head group size) and concentration influence the reaction in NaOH-QAS micellar solutions. The NaOH-QAS systems, with surfactant concentration below critical micelle concentration (CMC), showed high activity giving high conversion and flavanone selectivity. This result was interpreted as substrate induced micellization and favorable interactions of surfactant molecules with reactants and intermediates. The reduction in conversion and selectivity of flavanone was observed with NaOH-QAS solutions having surfactant concentration at CMC or above CMC, which was due to strong solubilization of o-hydroxy acetophenone and intermediates in the micelles. The highest conversion (92% in 24 h) and selectivity of flavanone (98%) were obtained with NaOH-cetylpyridinium chloride (NaOH-C(16)PQAS) system at surfactant concentration below CMC. The -OH group present in o-hydroxy acetophenone was observed to be responsible for its less reactivity in the aldol reaction. The reusability of NaOH-cationic surfactant solution was examined for three reaction cycles. (C) 2015 Elsevier B.V. All rights reserved.
• The cytotoxic effect of spiroflavanone derivatives, their binding ability to human serum albumin (HSA) and a DFT study on the mechanism of their synthesis
  作者：Elzbieta Budzisz、Piotr Paneth、Inacrist Geromino、Tadeusz Muzioł、Marek Rozalski、Urszula Krajewska、Paulina Pipiak、Michał B. Ponczek、Magdalena Małecka、Bogumiła Kupcewicz

  DOI：10.1016/j.molstruc.2017.02.037

  日期：2017.6

  the reaction mechanism between diazomethane and selected benzylideneflavanones, their lipophilicity, and their binding ability to human serum albumin. The cytotoxic effect was determined on two human leukaemia cell lines (HL-60 and NALM-6) and melanoma WM-115 cells, as well as on normal human umbilical vein endothelial cells (HUVEC). The highest cytotoxicity was exhibited by compound B7: it was found

  摘要 本文研究了 9 种具有螺吡唑啉结构的化合物的细胞毒作用，并确定了重氮甲烷与选定的亚苄基黄烷酮之间的反应机制、它们的亲脂性以及它们与人血清白蛋白的结合能力。对两种人白血病细胞系（HL-60 和 NALM-6）和黑色素瘤 WM-115 细胞以及正常人脐静脉内皮细胞 (HUVEC) 确定了细胞毒性作用。化合物 B7 表现出最高的细胞毒性：发现它对所有三种癌细胞系的 IC50 均小于 10 μM，对正常细胞 (HUVEC) 的敏感性低 5 至 12 倍。所有化合物在人血清白蛋白结合中表现出相当的亲和能（从 -8.1 到 -8.6 kcal mol-1），但它们的结合位点因取代基而异。