7-acetoxy-3-(p-tolyl)-2H-chromen-2one | 20050-73-1

• 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: 7-acetoxy-3-(p-tolyl)-2H-chromen-2one
• 英文别名: 7-acetoxy-3-(p-tolyl)coumarin；7-acetoxy-3-(4-methylphenyl)coumarin；[3-(4-Methylphenyl)-2-oxochromen-7-yl] acetate；[3-(4-methylphenyl)-2-oxochromen-7-yl] acetate
• CAS: 20050-73-1
• 化学式: C₁₈H₁₄O₄
• 分子量: 294.307
• InChiKey: GYXAMFGRWGZETD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-acetoxy-3-(p-tolyl)-2H-chromen-2one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以1.25 g的产率得到7-hydroxy-3-(p-tolyl)-2H-chromen-2-one
  参考文献：
  名称：

  含甲苯基和甲苯磺酰基香豆素酞菁的光物理和光化学性质及比较

  摘要：

  在这项研究中，外围和非外围取代的 Zn(II) 酞菁配合物是由 7-hydroxy -3-( p -tolyl)coumarin和 7-hydroxy-3-( p -tosyl)coumarin 化合物合成的。使用元素分析、FT-IR、UV-Vis、荧光1对合成的新化合物进行表征HNMR 光谱和 MALDI-TOF 质谱。所有合成的酞菁配合物在丙酮、二氯甲烷、氯仿、吡啶和乙酸乙酯等有机溶剂中均表现出良好的溶解性。使用 1,4-苯醌和碘化钾作为猝灭剂研究了荧光猝灭行为。在二甲亚砜中检测了这些新酞菁的光物理（荧光量子产率和寿命）和光化学（单氧和光降解量子产率）特性。含有 7-hydroxy-3-( p -tolyl)coumarin的酞菁络合物比含有 7-hydroxy-3-( p -tolyl)coumarin 的酞菁络合物具有更高的单线态氧量子产率-甲苯磺酰）香豆素。香豆素外围结合的酞菁比

  DOI：

  10.1016/j.molstruc.2022.134565
• 作为产物：
  描述：

  对甲基苯乙酸 、 2,4-二羟基苯甲醛 在 乙酸酐 、 三乙胺 作用下， 反应 0.17h， 以70%的产率得到7-acetoxy-3-(p-tolyl)-2H-chromen-2one
  参考文献：
  名称：

  Molecular Docking-Based Design and Development of a Highly Selective Probe Substrate for UDP-glucuronosyltransferase 1A10

  摘要：

  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.

  DOI：

  10.1021/acs.molpharmaceut.7b00871

文献信息

• Through‐Bond Energy Transfer Cassettes with Minimal Spectral Overlap between the Donor Emission and Acceptor Absorption: Coumarin–Rhodamine Dyads with Large Pseudo‐Stokes Shifts and Emission Shifts
  作者：Weiying Lin、Lin Yuan、Zengmei Cao、Yanming Feng、Jizeng Song

  DOI：10.1002/anie.200904515

  日期：2010.1.8

  Cassette recording: A new class of coumarin–rhodamine through‐bond energy‐transfer (TBET) cassettes with minimal spectral overlap between the donor emission and the acceptor absorption (see picture) show large pseudo‐Stokes shifts (up to 230 nm) and emission shifts (up to 170 nm). The utility of this TBET platform for TBET‐based probe development was demonstrated by a new ratiometric fluorescence pH

  盒式磁带记录：新型香豆素-若丹明通过键能量转移（TBET）盒带，在供体发射和受体吸收之间的光谱重叠最小（参见图片），显示出大的伪斯托克斯位移（最大230 nm）和发射位移（最大170 nm）。新型比例荧光pH探针证明了该TBET平台在基于TBET的探针开发中的实用性。
• PROCESS FOR PRODUCING (S)-EQUOL
  申请人：DR. REDDY'S LABORATORIES LIMITED

  公开号：US20150057456A1

  公开（公告）日：2015-02-26

  The present application relates to an improved process for the preparation of (S)-equol (1). The present application also relates to novel intermediates of formula (7), (7A), (8) and (9) and their use for the synthesis of (5)-equol.

  本申请涉及一种改进的制备(S)-异黄酮(1)的方法。本申请还涉及公式(7)、(7A)、(8)和(9)的新中间体及其用于合成(5)-异黄酮的应用。
• US9051291B2
  申请人：——

  公开号：US9051291B2

  公开（公告）日：2015-06-09
• 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.
• Photophysical and photochemical properties and comparison of tolyl and tosyl coumarin-bearing phthalocyanines
  作者：Zehra Kazancıçok、Hatice Esra Güler、Mücahit Özdemir、Mehmet Pişkin、Mustafa Bulut、Bahattin Yalçın、Ümit Salan

  DOI：10.1016/j.molstruc.2022.134565

  日期：2023.2

  solubility in organic solvents such as acetone, dichloromethane, chloroform, pyridine, and ethyl acetate. Fluorescent quenching behavior was investigated using 1,4-benzoquinone and potassium iodide as a quencher. The photophysical (fluorescent quantum yields and lifetimes) and photochemical (single oxygen and photodegradation quantum yields) properties of these new phthalocyanines were examined in

  在这项研究中，外围和非外围取代的 Zn(II) 酞菁配合物是由 7-hydroxy -3-( p -tolyl)coumarin和 7-hydroxy-3-( p -tosyl)coumarin 化合物合成的。使用元素分析、FT-IR、UV-Vis、荧光1对合成的新化合物进行表征HNMR 光谱和 MALDI-TOF 质谱。所有合成的酞菁配合物在丙酮、二氯甲烷、氯仿、吡啶和乙酸乙酯等有机溶剂中均表现出良好的溶解性。使用 1,4-苯醌和碘化钾作为猝灭剂研究了荧光猝灭行为。在二甲亚砜中检测了这些新酞菁的光物理（荧光量子产率和寿命）和光化学（单氧和光降解量子产率）特性。含有 7-hydroxy-3-( p -tolyl)coumarin的酞菁络合物比含有 7-hydroxy-3-( p -tolyl)coumarin 的酞菁络合物具有更高的单线态氧量子产率-甲苯磺酰）香豆素。香豆素外围结合的酞菁比