4-(naphthalen-2-yl)chroman-2-one | 1224738-65-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 4-(naphthalen-2-yl)chroman-2-one
• 英文别名: 3,4-dihydro-4-(2-naphthyl)coumarin；4-Naphthalen-2-yl-3,4-dihydrochromen-2-one；4-naphthalen-2-yl-3,4-dihydrochromen-2-one
• CAS: 1224738-65-1
• 化学式: C₁₉H₁₄O₂
• 分子量: 274.319
• InChiKey: OXIGWXCVWYFLBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  (E)-ethyl 2-hydroxycinnamate 、 2,4,6-tris-(2-naphthyl)boroxine 在 hydroxo(1,5-cyclooctadiene)rhodium (I) dimer 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以82%的产率得到4-(naphthalen-2-yl)chroman-2-one
  参考文献：
  名称：

  Rhodium-Catalyzed Domino Conjugate Addition−Cyclization Reactions for the Synthesis of a Variety of N- and O-Heterocycles: Arylboroxines as Effective Carbon Nucleophiles

  摘要：

  Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.

  DOI：

  10.1021/ol100610v

文献信息

• Organic Solvent‐free Asymmetric 1,4‐Addition in Liquid‐ or Solid‐State using Conventional Stirring Catalyzed by a Chiral Rhodium Complex Developed as a Homogeneous Catalyst
  作者：Toshinobu Korenaga、Hiroto Kori、Shota Asai、Ryo Kowata、Masayuki Shirai

  DOI：10.1002/cctc.202001479

  日期：2020.12.4

  Organic solvent‐free asymmetric 1,4‐addition of arylboronic acids to enone substrates was performed by using a chiral rhodium complex catalyst developed as a homogeneous catalyst. Reactions catalyzed by [RhOH(cod)]2 with chiral diphosphine ligands in liquid‐ or solid‐state proceeded to give chiral 1,4‐adducts in high yield with enantioselectivities up to ca. 100 % ee by conventional stirring without

  使用开发为均相催化剂的手性铑配合物催化剂，可将无有机溶剂的芳烃硼酸不对称1,4加成到烯酮基质上。[RhOH（cod）] 2催化的反应用液态或固态的手性二膦配体制备高产率的手性1,4加合物，对映选择性高达。通过常规搅拌无需机械化学作用（例如球磨）即可获得100％ee。在静态条件下也进行了固相反应，但1,4加合物的对映选择性略有下降。固态反应的SEM观察表明没有生成纳米颗粒催化剂。通过使用最少的必需有机溶剂进行更绿色的纯化，可以将无有机溶剂的反应应用于克级合成。
• Palladium Catalyzed Enantioselective Hayashi–Miyaura Reaction for Pharmaceutically Important 4-Aryl-3,4-dihydrocoumarins
  作者：Jixing Lai、Chen Yang、René Csuk、Baoan Song、Shengkun Li

  DOI：10.1021/acs.orglett.1c04366

  日期：2022.2.18

  The first palladium-catalyzed asymmetric addition of arylboronic acids to coumarins was successfully established, providing a straightforward asymmetric approach to achieving pharmaceutically important 4-aryl-3,4-dihydrocoumarins. This methodology features easily accessible and bench-stable ligands, a wide substrate scope, mild conditions, and accommodation of electron-withdrawing arylboronic acids

  成功地建立了第一个钯催化的芳基硼酸不对称加成香豆素，为获得药学上重要的 4-aryl-3,4-dihydrocoumarins 提供了一种直接的不对称方法。该方法的特点是易于获得和稳定的配体、广泛的底物范围、温和的条件以及吸电子芳基硼酸的适应性。