(3H-benzo[f]chromen-2-yl)(phenyl)methanone | 1286746-16-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 高异黄酮
• 英文名称: (3H-benzo[f]chromen-2-yl)(phenyl)methanone
• 英文别名: 3H-naphtho[2,1-b]pyran-2-ylphenylmethanone；3H-benzo[f]chromen-2-yl(phenyl)methanone
• CAS: 1286746-16-4
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: HNJBBCUDTFXBOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-bromo-3-phenylprop-2-yne 在 iron(III) chloride 、 potassium carbonate 作用下， 以 硝基甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 (3H-benzo[f]chromen-2-yl)(phenyl)methanone
  参考文献：
  名称：

  Iron-Catalyzed Synthesis of Functionalized 2H-Chromenes via Intramolecular Alkyne−Carbonyl Metathesis

  摘要：

  An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, brow, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.

  DOI：

  10.1021/jo2000012

文献信息

• Pyridinium triflate catalyzed intramolecular alkyne-carbonyl metathesis reaction of O-propargylated 2-hydroxyarylaldehydes
  作者：Manoj Kumar Saini、Harshita Singh Korawat、Shashi Kant Verma、Ashok K. Basak

  DOI：10.1016/j.tetlet.2020.152657

  日期：2020.12

  3,5-Dibromopridinium trifluoromethanesulfonate catalyzes the intramolecular alkyne-carbonyl metathesis reaction of a variety of O-propargylated 2-hydroxyarylaldehydes and ketones bearing alkyl, aryl and heteroaryl substituted internal alkynes to provide various 3-(hetero)aroyl 2H-chromenes in high yields.

  3,5-二溴pri鎓三氟甲磺酸盐催化各种O-炔丙基化的2-羟基芳基醛和带有烷基，芳基和杂芳基取代的内部炔烃的分子的内炔-羰基复分解反应，从而在高浓度下提供各种3-（杂）芳酰基2 H-色烯产量。
• Cu(II)-Catalyzed [3 + 1 + 1 + 1] Cyclization of 1,3-Diketones and 2-Naphthols Using <i>N</i>,<i>N</i>-Dimethylethanolamine as a Dual Carbon Synthon for the Synthesis of 2<i>H</i>-Chromenes
  作者：Meiqi Geng、Minzhao Huang、Jinqiang Kuang、Weiwei Fang、Xuqiong Xiao、Maozhong Miao、Yongmin Ma

  DOI：10.1021/acs.joc.3c01849

  日期：2024.1.5

  Reactions with diverse C1 synthons to realize homologation were well explored. However, homologations occurring twice with one C1 synthon in a reaction were less reported. We disclose herein a Cu(II)-catalyzed novel and efficient synthesis of 2H-chromenes from 2-naphthols, 1,3-diketones, and N,N-dimethylethanolamine (DMEA) as a dual carbon synthon. Various 2H-chromenes with different functional groups

  充分探索了与不同 C1 合成子的反应以实现同系化。然而，在一个反应​​中与一个 C1 合成子发生两次同系的报道较少。我们在此公开了作为双碳合成子的Cu(II)催化的由2-萘酚、1,3-二酮和N , N-二甲基乙醇胺(DMEA)新颖且有效地合成2H-色烯的方法。具有不同官能团的各种2H-色烯以中等至良好的产率构建。这是 DMEA 作为双 C1 合成子的第一份报告。
• Boron trifluoride–etherate in fluorinated alcohols: A powerful promoter system for intramolecular alkyne–aldehyde metathesis of o-(3-arylpropargyloxy)benzaldehydes
  作者：Arup Jyoti Das、Runjun Devi、Sajal Kumar Das

  DOI：10.1016/j.tetlet.2018.10.040

  日期：2018.11

  Boron trifluoride-etherate (BF3 center dot OEt2) in 2,2,2-trifluoroethanol (TFE) was found to be a highly efficient promoter system for the intramolecular alkyne-aldehyde metathesis of o-(3-arylpropargyloxy)benzaldehydes. The reaction produces the corresponding 3-aroyl-2H-chromenes in excellent yields under metal free conditions. (C) 2018 Elsevier Ltd. All rights reserved.
• Iron-Catalyzed Synthesis of Functionalized 2<i>H</i>-Chromenes via Intramolecular Alkyne−Carbonyl Metathesis
  作者：Krishnendu Bera、Soumen Sarkar、Srijit Biswas、Sukhendu Maiti、Umasish Jana

  DOI：10.1021/jo2000012

  日期：2011.5.6

  An iron-catalyzed intramolecular alkyne-aldehyde metathesis strategy of the alkynyl ether of salicylaldehyde derivatives has been developed which works under mild reaction conditions to produce the functionalized 2H-chromene derivatives. This protocol is compatible toward a wide range of functional groups, such as methoxy, fluoro, chloro, brow, and phenyl groups. This method provides an atom-economical and environmentally friendly approach for the synthesis of a series of substituted 2H-chromenes.