3-(3-methylbenzoyl)-4-phenyl-2H-chromen-2-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3-(3-methylbenzoyl)-4-phenyl-2H-chromen-2-one
• 英文别名: 3-(3-Methylbenzoyl)-4-phenylchromen-2-one；3-(3-methylbenzoyl)-4-phenylchromen-2-one
• 化学式: C₂₃H₁₆O₃
• 分子量: 340.378
• InChiKey: INGSXDKCXLQQRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  phenyl 3-phenylpropiolate 、 3-methylphenyloxoacetic acid 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以72%的产率得到3-(3-methylbenzoyl)-4-phenyl-2H-chromen-2-one
  参考文献：
  名称：

  银介导的炔酸和α-酮酸通过级联双CC键形成香豆素的自由基环化反应

  摘要：

  已经开发了一种新颖且方便的银介导的自由基环化方法，该方法通过在温和条件下通过双CC键形成α-酮酸将炔酸酯直接双官能化来合成香豆素衍生物。该新方法是高效且实用的，并且原料易于制备。本方法应为构建香豆素基序提供有用的策略。

  DOI：

  10.1021/jo502474z

文献信息

• The visible-light-induced acylation/cyclization of alkynoates with acyl oximes for the construction of 3-acylcoumarins
  作者：Quan Zhou、Fang-Ting Xiong、Pu Chen、Bi-Quan Xiong、Ke-Wen Tang、Yu Liu

  DOI：10.1039/d1ob01568k

  日期：——

  by the visible-light-induced acylation/cyclization of alkynoates with various acyl oxime compounds in acetonitrile. The difunctionalization of carbon–carbon triple bonds precedes the generation of iminyl radicals, which is followed by the formation of acyl radicals. The acyl radicals then attack the carbon–carbon triple bonds, followed by 5-exo-trig cyclization and 1,2-ester migration. This strategy

  描述了一种以氮为中心的自由基介导的碳-碳键断裂策略来合成功能化的 3-酰基香豆素。该策略是通过可见光诱导的炔酸酯与乙腈中的各种酰基肟化合物的酰化/环化来实现的。碳-碳三键的双官能化先于亚氨基自由基的产生，然后是酰基自由基的形成。然后酰基自由基攻击碳-碳三键，然后进行 5 -exo-trig环化和 1,2-酯迁移。该策略具有广泛的底物适应性和良好的取代基耐受性。
• Silver-Mediated Radical Cyclization of Alkynoates and α-Keto Acids Leading to Coumarins via Cascade Double C–C Bond Formation
  作者：Kelu Yan、Daoshan Yang、Wei Wei、Fen Wang、Yuanyuan Shuai、Qiannan Li、Hua Wang

  DOI：10.1021/jo502474z

  日期：2015.2.6

  A novel and convenient silver-mediated radical cyclization method for the synthesis of coumarin derivatives via the direct difunctionalization of alkynoates with α-keto acids through double C–C bond formation under mild conditions has been developed. This new method is highly efficient and practical, and the starting materials are readily prepared. The present method should provide a useful strategy

  已经开发了一种新颖且方便的银介导的自由基环化方法，该方法通过在温和条件下通过双CC键形成α-酮酸将炔酸酯直接双官能化来合成香豆素衍生物。该新方法是高效且实用的，并且原料易于制备。本方法应为构建香豆素基序提供有用的策略。
• Visible-light-mediated cascade difunctionalization/cyclization of alkynoates with acyl chlorides for synthesis of 3-acylcoumarins
  作者：Yu Liu、Qiao-Lin Wang、Cong-Shan Zhou、Bi-Quan Xiong、Pan-Liang Zhang、Shuang-Jian Kang、Chang-An Yang、Ke-Wen Tang

  DOI：10.1016/j.tetlet.2018.04.033

  日期：2018.5

  A new visible-light-mediated radical cyclization of alkynoates with acyl chlorides is described for the one-pot construction of diverse 3-acylcoumarins with high efficiency and selectivity. This method is successful by sequential difunctionalization of an alkynes CC triple bond with the CCl bonds of acyl chloride and aromatic C(sp2)H bonds. The cyclization is proposed to simultaneously form two new

  描述了一种新型的可见光介导的炔烃与酰氯的自由基环化反应，可用于一锅式构建各种3-酰基香豆素，具有高效率和选择性。该方法通过将炔烃C C三键与酰氯的C Cl键和芳族C（sp 2）H键依次双官能化而成功。提议将环化同时形成两个新的碳-碳键，并涉及自由基酰化，5-exo-trig环化和酯迁移。
• Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities
  作者：Kazuki Kawaai、Tomoaki Yamaguchi、Eiji Yamaguchi、Satoshi Endo、Norihiro Tada、Akira Ikari、Akichika Itoh

  DOI：10.1021/acs.joc.7b02933

  日期：2018.2.16

  construct the 3-acyl-4-arylcoumarin framework from simple aldehyde with ynoate is described. The reaction proceeded through an acyl radical intermediate generated by hydrogen atom abstraction from aldehyde, followed by reaction with ynoate and then cyclization to afford coumarins. This valuable radical cyclization reaction gave over 20 coumarin derivatives in moderate to good yields with inexpensive 2-tBu-anthraquinone

  描述了一种新颖的光催化，由简单的醛与with酸酯构成3-酰基-4-芳基香豆素骨架。该反应通过从醛中夺取氢原子而产生的酰基自由基中间体进行，然后与矢酸盐反应，然后环化得到香豆素。这种有价值的自由基环化反应以廉价的2 - t丁蒽醌为催化剂，以中等至良好的收率得到了20多种香豆素衍生物。此外，对合成香豆素进行了5α-二氢睾酮（DHT）诱导的前列腺特异性抗原（PSA）分泌和雄激素依赖性CWR22Rv1细胞增殖的研究。
• Preparation of 3-Acyl-4-arylcoumarins via Metal-Free Tandem Oxidative Acylation/Cyclization between Alkynoates with Aldehydes
  作者：Xia Mi、Chenyang Wang、Mengmeng Huang、Yusheng Wu、Yangjie Wu

  DOI：10.1021/jo502220b

  日期：2015.1.2

  A new and efficient metal-free tandem acylation/cyclization of alkynoates with aldehydes was developed for the synthesis of 3-acyl-4-arylcoumarins. The reaction was achieved by the addition of acyl radical to alkynes and a C-H bond functionalization to form two new C-C bonds simultaneously.