3-benzoyl-8-bromo-2H-chromen-2-one | 1194476-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-8-bromo-2H-chromen-2-one
• CAS: 1194476-96-4
• 化学式: C₁₆H₉BrO₃
• 分子量: 329.15
• InChiKey: FZQRLIZJQREYNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.28
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-diisobutyl(styryl)aluminum 、 3-benzoyl-8-bromo-2H-chromen-2-one 在 copper(II) acetate monohydrate 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以86%的产率得到(E)-3-benzoyl-8-bromo-4-styrylchroman-2-one
  参考文献：
  名称：

  Asymmetric conjugate additions to 1,1′-diactivated cyclic enones—a comparative study

  摘要：

  A study of copper-phosphoramidite-catalysed ZnR2 and AlR3 additions to 1,1'-dicarbonyl-activated cyclic Michael acceptors has revealed high enantioselectivities for AlR3 (R = Me, Et) 1,4-addition to a range of 3-acylcoumarins (85-98% ee, trans:cis similar to 90:10) using commercial OF readily available ligands. Large substituents at the 6-position, and to some extent at the 5-position, of the coumarin are less well tolerated, nor is truncation of the coumarin motif to a comparable 2-acylcyclohexenone (ee values up to 78%). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.006
• 作为产物：
  描述：

  3-溴柳醛 、 苯甲酰乙酸乙酯 以87%的产率得到3-benzoyl-8-bromo-2H-chromen-2-one
  参考文献：
  名称：

  Asymmetric conjugate additions to 1,1′-diactivated cyclic enones—a comparative study

  摘要：

  A study of copper-phosphoramidite-catalysed ZnR2 and AlR3 additions to 1,1'-dicarbonyl-activated cyclic Michael acceptors has revealed high enantioselectivities for AlR3 (R = Me, Et) 1,4-addition to a range of 3-acylcoumarins (85-98% ee, trans:cis similar to 90:10) using commercial OF readily available ligands. Large substituents at the 6-position, and to some extent at the 5-position, of the coumarin are less well tolerated, nor is truncation of the coumarin motif to a comparable 2-acylcyclohexenone (ee values up to 78%). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.07.006

文献信息

• Highly enantioselective synthesis of dihydrocoumarin-fused dihydropyrans via the phosphine-catalyzed [4 + 2] annulation of allenones with 3-aroylcoumarins
  作者：Xiaoyu Han、Huanzhen Ni、Wai-Lun Chan、Xikun Gai、Yongjiang Wang、Yixin Lu

  DOI：10.1039/c6ob00955g

  日期：——

  Phosphine-catalyzed [4 + 2] annulation between 3-aroylcoumarins and allenones has been developed. In the presence of a dipeptide phosphine catalyst 7, dihydrocoumarin-fused dihydropyrans were prepared in high yields and with excellent enantioselectivities.

  已经开发了膦催化的3-芳酰基香豆素和异戊二烯之间的[4 + 2]环化反应。在二肽膦催化剂7的存在下，以高收率和优异的对映选择性制备了二氢香豆素稠合的二氢吡喃。
• Organocatalytic Asymmetric Cyclopropanation of 3-Acylcoumarins with 3-Halooxindoles: Access to Spirooxindole-cyclopropa[<i>c</i>]coumarin Compounds
  作者：Wei-Cheng Yuan、Chuan-Wen Lei、Jian-Qiang Zhao、Zhen-Hua Wang、Yong You

  DOI：10.1021/acs.joc.0c02653

  日期：2021.2.5

  diastereo- and enantioselective cyclopropanation reaction of 3-acylcoumarins with 3-halooxindoles catalyzed by an organocatalyst through a [2 + 1] Michael/intramolecular cyclization process was developed. This scenario provides a facile strategy to access spirooxindole-cyclopropa[c]coumarin compounds bearing three continuous stereocenters, including two vicinal quaternary all-carbon stereocenters with high

  通过[2 + 1] Michael /分子内环化过程，开发了3-酰基香豆素与3-卤代新多酚的高度非对映和对映选择性的环丙烷化反应。此方案提供了一种简便的策略，可访问带有三个连续立体中心（包括两个邻位季铵全碳立体中心，具有高到极好的非对映和对映选择性的螺环吲哚-环丙烷[ c ]香豆素化合物）。HRMS研究表明，叶立铵中间体在催化过程中至关重要。
• 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。