4-(4-羟基苯基)-7-甲氧基-3-苯基色烯-2-酮 | 33257-83-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 中文名称: 4-(4-羟基苯基)-7-甲氧基-3-苯基色烯-2-酮
• 英文名称: 4-(4-hydroxyphenyl)-7-methoxy-3-phenyl-2H-chromen-2-one
• 英文别名: 4-(4-hydroxyphenyl)-7-methoxy-3-phenylchromen-2-one；4-(4-hydroxy-phenyl)-7-methoxy-3-phenyl-chromen-2-one；4-(4-Hydroxyphenyl)-7-methoxy-3-phenyl-2H-1-benzopyran-2-one
• CAS: 33257-83-9
• 化学式: C₂₂H₁₆O₄
• 分子量: 344.367
• InChiKey: GCVBTSKNEVRIFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-羟基苯基)-7-甲氧基-3-苯基色烯-2-酮 在 palladium on activated charcoal sodium hydroxide 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 23.5h， 生成 (+/-)-cis-7-methoxy-3-phenyl-4-(4-(2-pyrrolidinoethoxy)phenyl)chromane
  参考文献：
  名称：

  新型顺式3,4-二芳基-羟基苯并二氢吡喃类化合物作为雌激素受体高亲和力部分激动剂的合成与药理评价。

  摘要：

  报道了许多顺式3,4-二芳基-羟基-苯并二氢吡喃的合成和体外药理学评估，以及对体内组织选择性雌激素部分激动剂NNC 45-0781进行彻底体内分析的结果[3 ，（-）-（3S，4R）-7-羟基-3-苯基-4-（4-（2-吡咯烷基乙氧基）苯基）苯并二氢吡喃]。这些研究表明，NNC 45-0781是预防绝经后骨质疏松症以及治疗与内源性雌激素产生损失有关的其他健康问题的非常有前途的候选人。

  DOI：

  10.1016/s0968-0896(01)00257-7
• 作为产物：
  描述：

  3-甲氧基苯酚 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-羰基二咪唑 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-(4-羟基苯基)-7-甲氧基-3-苯基色烯-2-酮
  参考文献：
  名称：

  Lead identification of a potent benzopyranone selective estrogen receptor modulator

  摘要：

  Starting from a phenol screening hit (6), three series of benzopyranone selective estrogen receptor modulators (SERMs) have been designed, synthesized, and analyzed for both estrogen receptor alpha binding affinity and in vitro activity in two cell assays. The lead compound identified, SP500263 (13), was more potent than raloxifene and tamoxifen in a cell-based assay measuring inhibition of interleukin-6 release. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.081

文献信息

• Smooth Conversion of 3,4-Diarylcoumarins and 3,4,5-Triaryl-2(5<i>H</i>)-furanones to 2<i>H</i>-Chromene and 2,5-Dihydrofuran Derivatives with Dimethyl Sulfide-Borane Complex
  作者：Parul Verma、Sangeeta Singh、D. K. Dikshit、Suprabhat Ray

  DOI：10.1055/s-1988-27468

  日期：——

  Reaction of 3,4-diarylcoumarins (3,4-diaryl-2-oxo-2H-1-benzopyrans) and 3,4,5-triaryl- 2(5H)-furanones with dimethyl sulfide-borane complex affords the corresponding 2H-chromenes (2H-1-benzopyrans) and 2.5-dihydrofurans in high yields. 3,4-Diaryl-2(5H)-furanones afford the corresponding furans.

  3,4-二芳基香豆素（3,4-二芳基-2-氧代-2H-1-苯并吡喃）和 3,4,5-三芳基-2(5H)-呋喃酮与二甲基硫醚-硼烷络合物反应，可以高产率地得到相应的 2H-铬（2H-1-苯并吡喃）和 2.5-二氢呋喃。3,4-二芳基-2(5H)-呋喃酮可生成相应的呋喃。
• Design, synthesis, and anti-tumor activities of novel triphenylethylene–coumarin hybrids, and their interactions with Ct-DNA
  作者：Hua Chen、Shuai Li、Yuchao Yao、Likai Zhou、Jianpeng Zhao、Yunjing Gu、Kerang Wang、Xiaoliu Li

  DOI：10.1016/j.bmcl.2013.07.009

  日期：2013.9

  Novel triphenylethylene-coumarin hybrid derivatives containing different amounts of amino side chains Were designed and synthesized in good yields under microwave radiation. The derivatives 5b-d which possessed two amino side chains (except morpholinyl) showed a broad-spectrum and good anti-proliferative activity against five tumor cells and low cytotoxicity in osteoblast. UV-vis, fluorescence, and circular dichroism (CD) spectroscopies and thermal denaturation exhibited that compounds 10c, 5c, and 13c bearing amino side chain (except morpholinyl) on 4-phenyl had significant interactions with Ct-DNA by the intercalative mode of binding. Structure-activity relationships (SARs) analysis suggested that the amino alkyl chain would play an important role both in the compounds against tumor cells proliferation and their interactions with DNA. (C) 2013 Elsevier Ltd. All rights reserved.
• Arora, P. K.; Ray, Suprabhat, Journal fur praktische Chemie (Leipzig 1954), 1981, vol. 323, # 5, p. 850 - 852
  作者：Arora, P. K.、Ray, Suprabhat

  DOI：——

  日期：——
• 7-Methoxy-2,2-dimethyl-3-phenyl-4-(4-hydroxyphenyl)-2<i>H</i>-1-benzopyran
  作者：S. Ray、S. Sarkhel、P. R. Maulik、E. Lobkovsky、J. Clardy

  DOI：10.1107/s0108270197012341

  日期：1998.1.15

  The crystal structure of the title compound, C24H22O3, shows that both the pendant phenyl substituents at C3 and C4 have a twist conformation, while the pyran ring adopts a distorted sofa conformation due to puckering at C2 by the dimethyl substitutions.
• J. Med. Chem. 1976, 19, 276-279
  作者：

  DOI：——

  日期：——