3-benzoyl-7-methyl-chromen-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-7-methyl-chromen-2-one
• 英文别名: 3-benzoyl-7-methyl-2H-chromen-2-one；3-benzoyl-7-methyl-coumarin；3-Benzoyl-7-methyl-cumarin；3-Benzoyl-7-methylchromen-2-one
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: LFJUWBHOLXZDPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-7-methyl-chromen-2-one 、 苯甲酰甲基-二甲基-溴化硫 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以90%的产率得到(5-methyl-2-oxo-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-1, 1a-diyl)bis(phenylmethanone)
  参考文献：
  名称：

  稳定的硫叶立德介导的环丙烷化和 3-酰基-2H-色酮及其亚胺的正式 [4+1] 环加成

  摘要：

  研究了稳定的硫叶立德介导的环丙烷化和 3-酰基-2H-色酮及其亚胺的正式 [4+1] 环加成。转化可以在温和的条件下进行，并显示出具有广泛的底物范围和显着的官能团耐受性；此外，反应以优异的区域选择性进行。因此，它们是一锅法合成高度官能化的环丙烷和二氢吡咯稠合的 chromen-2-one 衍生物的有效方法。

  DOI：

  10.1002/ejoc.201600759
• 作为产物：
  描述：

  7-甲基香豆素 、 苯甲醛 在 叔丁基过氧化氢 作用下， 以 水 、 氯苯 为溶剂， 反应 20.0h， 以72%的产率得到3-benzoyl-7-methyl-chromen-2-one
  参考文献：
  名称：

  A Regioselective Metal-Free Construction of 3-Aroyl Coumarins by Csp2-H Functionalization

  摘要：

  A successive metal-free TBHP-mediated regioselective C-H functionalization of coumarins toward expedient synthesis of 3-aroyl coumarins is unveiled. The ongoing method conducted through the reaction of either coumarins or coumarin-3-carboxylic acids with aromatic aldehydes. The optimized reaction condition also worked well with benzyl alcohols and styrenes as surrogates for aldehydes, which bear latent carbonyl functionality.

  DOI：

  10.1021/acs.joc.6b02051

文献信息

• Tunable Phosphine-Triggered Cascade Reactions of MBH Derivatives and 3-Acyl-2<i>H</i>-chromen-2-ones: Highly Selective Synthesis of Diverse Chromenones
  作者：Wei Yuan、Hu-Fei Zheng、Zhi-Hua Yu、Zi-Long Tang、De-Qing Shi

  DOI：10.1002/ejoc.201301358

  日期：2014.1

  Diverse chromenones were synthesized through tunable phosphine-mediated cascade reactions between 3-acyl-2H-chromen-2-ones and Morita–Baylis–Hillman (MBH) derivatives. With different phosphine loadings and reaction temperatures, MBH derivatives act either as C1 or C3 synthons for the construction of potential biologically active 3-dihydrofuran-fused chromen-2-ones, 4-allyl-3-acyl-chromen-2-ones, or

  通过可调膦介导的 3-acyl-2H-chromen-2-ones 和 Morita-Baylis-Hillman (MBH) 衍生物之间的级联反应合成了多种色酮。在不同的膦负载量和反应温度下，MBH 衍生物充当 C1 或 C3 合成子，用于构建潜在的生物活性 3-二氢呋喃稠合 chromen-2-ones、4-allyl-3-acyl-chromen-2-ones，或6H-benzo[c]chromen-6-ones。该方法具有条件温和、后处理简单、底物适用范围广等优点，可有效合成多种色酮衍生物。
• 3-KETOCOUMARINES FOR LED PHOTOCURING
  申请人：LAMBERTI SPA

  公开号：US20150259316A1

  公开（公告）日：2015-09-17

  The present invention relates to 3-ketocoumarines which can be used as photoinitiators in LED photocuring and to a process for curing compositions comprising said 3-ketocoumarines.

  本发明涉及可用作LED光固化中的光引发剂的3-酮香豆素，以及用于固化包含该3-酮香豆素的组合物的方法。
• A copper-catalyzed tandem reaction for the construction of coumarin fused 9H-pyrrolo[1,2-a]indoles
  作者：Shao-Jing Jin、Jiao-Mei Guo、Yan-Shuo Zhu、Qi-Lin Wang、Zhan-Wei Bu

  DOI：10.1039/c7ob02307c

  日期：——

  An efficient copper-catalyzed Friedel-Crafts alkylation/cyclization/isomerization sequence of 3-arylcarbonyl coumarins and 3-methyl indole was developed to afforded a wide range of functionalized coumarin fused 9H-pyrrolo[1,2-a]indoles, which featured with a 6-6-5-5-6 pentacyclic core, in 34-99% yields. Moreover, gram-scale experiment and chemical transformations were conducted to demonstrate the synthetic

  开发了3-芳基羰基香豆素和3-甲基吲哚的铜催化的Friedel-Crafts烷基化/环化/异构化序列，以提供各种功能化的香豆素稠合的9 H-吡咯并[1,2- a ]吲哚，具有6-6-5-5-6五环核，产率为34-99％。此外，进行了克级实验和化学转化以证明该方案的合成价值。
• DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate
  作者：Ying Wang、Zhi-Hua Yu、Hu-Fei Zheng、De-Qing Shi

  DOI：10.1039/c2ob26300a

  日期：——

  DABCO-catalyzed [4 + 2] and Bu3P-catalyzed [3 + 2] cycloadditions between 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate were developed for the synthesis of dihydropyran-fused and cyclopenten-fused chromen-2-ones with high regio- and stereo-selectivities, respectively. The synthetic procedures have the advantages of mild reaction conditions, convenient handling and good atom economy as well as a wide substrate scope, which make this method useful for the synthesis of potentially biologically active dihydropyran-fused and cyclopenten-fused chromen-2-ones derivatives. Possible reaction mechanisms have also been proposed on the basis of previous literature and our investigation.

  开发了 DABCO 催化的 [4 + 2] 和 Bu3P 催化的 [3 + 2] 3-酰基-2H-色烯酮与 2,3-丁二烯酸乙酯之间的环加成反应，用于合成二氢吡喃稠合和环戊烯稠合色烯- 2-one 分别具有高区域选择性和立体选择性。该合成方法具有反应条件温和、操作方便、原子经济性好、底物范围广等优点，可用于合成具有潜在生物活性的二氢吡喃稠合和环戊烯稠合苯并吡喃-2-酮衍生物。 。根据之前的文献和我们的研究，还提出了可能的反应机制。
• Diversity-Oriented Synthesis of Coumarin-Fused Cyclopentanones via a Nucleophilic Phosphine Controlled Cascade Reaction
  作者：Qi Huang、Junfeng Fu、Xiaoyu Han、Zhixin Chang、Wenhao Gan、Yongjiang Wang

  DOI：10.1055/s-0041-1738399

  日期：2022.8

  phosphine-promoted intermolecular annulation reaction of functionalized 3-benzoyl coumarin with alkynone has been disclosed. This reaction was found to be highly dependent on the nucleophilicity of the phosphine. Two classes of coumarin-fused cyclopentanones were selectively afforded in moderate to good yields with excellent diastereoselectivities under the mild reaction conditions.

  已公开了一种膦促进的官能化 3-苯甲酰基香豆素与炔酮的分子间环化反应。发现该反应高度依赖于膦的亲核性。在温和的反应条件下，两类香豆素稠合的环戊酮以中等至良好的产率选择性地提供，并具有优异的非对映选择性。