3-(4-methoxyphenyl)-2-oxo-2H-chromen-7-yl acetate | 66267-83-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(4-methoxyphenyl)-2-oxo-2H-chromen-7-yl acetate
• 英文别名: 7-acetoxy-3-(4-methoxyphenyl)chromen-2-one；7-acetoxy-3-(4-methoxyphenyl)coumarin；7-acetoxy-3-(4-methoxy-phenyl)-coumarin；7-Acetoxy-3-(4-methoxy-phenyl)-cumarin；7-Acetoxy-4'-methoxy-3-phenylcoumarin；[3-(4-methoxyphenyl)-2-oxochromen-7-yl] acetate
• CAS: 66267-83-2
• 化学式: C₁₈H₁₄O₅
• mdl: MFCD06405902
• 分子量: 310.306
• InChiKey: KERJTTDKXIXSLN-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  496.2±45.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-2-oxo-2H-chromen-7-yl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以73%的产率得到7-hydroxy-3-(4-methoxyphenyl)-2H-chromen-2-one
  参考文献：
  名称：

  两种用于手性胺和手性羧酸荧光检测的香豆素型衍生试剂的合成和评估

  摘要：

  据报道合成了两种荧光香豆素型手性衍生剂（4和11）。通过Mitsunobu反应将手性侧链引入香豆素的7位。这两个香豆素在该侧链上带有一个游离氨基或一个羧基，使它们可用于进一步的转化。手性原型药物与4或11的结合物是通过将分析物的羧基与试剂的胺基进行酰胺偶联来制备的，反之亦然。证明了在普通C18色谱柱上通过非手性高效液相色谱（HPLC）分离出七个非对映体共轭物。手性25：957–964，2013。©2013 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22240
• 作为产物：
  描述：

  2,4-二羟基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙酸酐 作用下， 生成 3-(4-methoxyphenyl)-2-oxo-2H-chromen-7-yl acetate
  参考文献：
  名称：

  Bhandari et al., Journal Of Scientific and Industrial Research, 1949, vol. 8 B, p. 189,190

  摘要：

  DOI：

文献信息

• Modified coumarins. 29. Synthesis of structural analogs of natural 6-arylfuro[3,2-g]chromen-7-ones
  作者：M. M. Garazd、Ya. L. Garazd、A. S. Ogorodniichuk、V. P. Khilya

  DOI：10.1007/s10600-009-9261-x

  日期：2009.3

  3-Substituted 6-arylfuro[3,2-g]chromen-7-ones, structural analogs of natural furocoumarins, were synthesized by linear annelation of a furan fragment to a 3-arylcoumarin system.

  3-取代的6-芳基呋喃[3,2-g]色烯-7-酮，作为天然呋喃香豆素的结构类似物，通过将呋喃片段线性连接到3-芳基香豆素体系中合成。
• Liquid-crystalline medium
  申请人：Merck Patent GmbH

  公开号：US11008515B2

  公开（公告）日：2021-05-18

  A liquid-crystalline medium which comprises at least one compound selected from the group of compounds of the formulae IA to IH, in which Z1 denotes a single bond, —CH2CH2—, —CH═CH—, —CH2O—, —OCH2—, —CF2O—, —OCF2—, —COO—, —OCO—, —C2F4—, —(CH2)4—, —CHFCHF—, —CF2CH2—, —CH2CF2—, —C≡C—, —CF═CF—, —CH═CHCHO— or —CH2CF2O—, and the use thereof for an active-matrix display, in particular based on the VA, PSA, PS-VA, PALC, FFS, PS-FFS, SA-VA, PS-IPS or IPS effect.

  一种液晶介质，包含至少一种选自式 IA 至 IH 化合物组的化合物、 其中 Z1 表示单键、-CH2CH2-、-CH═CH-、-CH2O-、-OCH2-、-CF2O-、-OCF2-、-COO-、-OCO-、-C2F4-、-(CH2)4-、-CHFCHF-、-CF2CH2-、-CH2CF2-、-C≡C-、-CF═CF-、-CH═CHCHO- 或 -CH2CF2O-、 以及将其用于有源矩阵显示器，特别是基于 VA、PSA、PS-VA、PALC、FFS、PS-FFS、SA-VA、PS-IPS 或 IPS 效果的显示器。
• Molecular Docking-Based Design and Development of a Highly Selective Probe Substrate for UDP-glucuronosyltransferase 1A10
  作者：Risto O. Juvonen、Sanna Rauhamäki、Sami Kortet、Sanna Niinivehmas、Johanna Troberg、Aleksanteri Petsalo、Juhani Huuskonen、Hannu Raunio、Moshe Finel、Olli T. Pentikäinen

  DOI：10.1021/acs.molpharmaceut.7b00871

  日期：2018.3.5

  Intestinal and hepatic glucuronidation by the UDP-glucuronosyltransferases (UGTs) greatly affect the bioavailability of phenolic compounds. UGT1A10 catalyzes glucuronidation reactions in the intestine, but not in the liver. Here, our aim was to develop selective, fluorescent substrates to easily elucidate UGT1A10 function. To this end, homology models were constructed and used to design new substrates, and subsequently, six novel C3-substituted (4-fluorophenyl, 4-hydroxyphenyl, 4-methoxyphenyl, 4-(dimethylamino)phenyl, 4-methylphenyl, or triazole) 7-hydroxycoumarin derivatives were synthesized from inexpensive starting materials. All tested compounds could be glucuronidated to nonfluorescent glucuronides by UGT1A10, four of them highly selectively by this enzyme. A new UGT1A10 mutant, 1A10-H210M, was prepared on the basis of the newly constructed model. Glucuronidation kinetics of the new compounds, in both wild-type and mutant UGT1A10 enzymes, revealed variable effects of the mutation. All six new C3-substituted 7-hydroxycoumarins were glucuronidated faster by human intestine than by liver microsomes, supporting the results obtained with recombinant UGTs. The most selective 4(dimethylamino)phenyl and triazole C3-substituted 7-hydroxycoumarins could be very useful substrates in studying the function and expression of the human UGT1A10.
• Kirkiacharian; Lormier; Resche-Rigon, Annales Pharmaceutiques Francaises, 2003, vol. 61, # 1, p. 51 - 56
  作者：Kirkiacharian、Lormier、Resche-Rigon、Bouchoux、Cérède

  DOI：——

  日期：——
• Highly soluble 7-oxy-3-(4-methoxyphenyl)coumarin bearing zinc phthalocyanines: Synthesis and investigation of photophysical and photochemical properties
  作者：Mehmet Pişkin、Mahmut Durmuş、Mustafa Bulut

  DOI：10.1016/j.jphotochem.2011.07.014

  日期：2011.9

  The synthesis of 7-oxy-3-(4-methoxyphenyl)coumarin-substituted peripherally and non-peripherally tetrakis- and peripherally octakis-tetrachloro zinc(II) phthalocyanine complexes are described for the first time in this study. The new compounds have been characterized by elemental analysis, IR, (1)H NMR, UV-vis spectroscopy and mass spectra. The photophysical and photochemical properties are important for photodynamic therapy applications and these properties of studied phthalocyanine complexes are investigated in N,N-dimethyl formamide (DMF). The effects of the number of the substitution and the position (peripheral or non-peripheral) on the photophysical and photochemical parameters of the zinc(II) phthalocyanine complexes are reported. The fluorescence quenching behaviour of the studied zinc(II) phthalocyanine complexes by the addition of 1,4-benzoquinone are also described. (C) 2011 Elsevier B.V. All rights reserved.