3H-naphtho[2,1-b]pyran-2-carboxylic acid | 659745-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3H-naphtho[2,1-b]pyran-2-carboxylic acid
• 英文别名: 3H-benzo[f]chromene-2-carboxylic acid
• CAS: 659745-57-0
• 化学式: C₁₄H₁₀O₃
• mdl: MFCD08445057
• 分子量: 226.232
• InChiKey: ZTKDKYOMXAZNKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3H-naphtho[2,1-b]pyran-2-carboxylic acid 在 4-二甲氨基吡啶 、 silver hexafluoroantimonate 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 copper(II) acetate monohydrate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 11,12,17-triphenylbenzo[5',6']chromeno[4',3':4,5]pyrido[2,1-a]isoquinolin-9(8H)-one
  参考文献：
  名称：

  Transformable Sulfoximine Assisted One-Pot Double Annulation of Vinylic C–H Bonds with Unactivated Alkynes

  摘要：

  The methylphenyl sulfoximine (MPS) directing group (DG) successfully promotes the one-pot double annulation of acrylic acids with alkynes under Ru catalysis, which is unprecedented. Diverse arrays of pyrido-fused-isoquinolinone skeletons are fabricated from acrylamides, creating two C-C and two C-N bonds in a single operation. The unsymmetrical annulation with two distinct alkynes is presented. The recovery of methylphenyl sulfoxide, a precursor of MPS, validates the synthetic adaptability of transformable-DG (T(f)DG) in C-H activation

  DOI：

  10.1021/acs.orglett.7b02824
• 作为产物：
  描述：

  3-cyano-2H-benzo[f]chromene 在 sodium hydroxide 作用下， 反应 6.0h， 以99%的产率得到3H-naphtho[2,1-b]pyran-2-carboxylic acid
  参考文献：
  名称：

  Pave, Gregoire; Chalard, Pierre; Viaud-Massuard, Marie-Claude, Synthesis, 2004, # 1, p. 121 - 127

  摘要：

  DOI：

文献信息

• Transformable Sulfoximine Assisted One-Pot Double Annulation of Vinylic C–H Bonds with Unactivated Alkynes
  作者：Majji Shankar、Tirumaleswararao Guntreddi、E. Ramesh、Akhila K. Sahoo

  DOI：10.1021/acs.orglett.7b02824

  日期：2017.10.20

  The methylphenyl sulfoximine (MPS) directing group (DG) successfully promotes the one-pot double annulation of acrylic acids with alkynes under Ru catalysis, which is unprecedented. Diverse arrays of pyrido-fused-isoquinolinone skeletons are fabricated from acrylamides, creating two C-C and two C-N bonds in a single operation. The unsymmetrical annulation with two distinct alkynes is presented. The recovery of methylphenyl sulfoxide, a precursor of MPS, validates the synthetic adaptability of transformable-DG (T(f)DG) in C-H activation
• Pave, Gregoire; Chalard, Pierre; Viaud-Massuard, Marie-Claude, Synthesis, 2004, # 1, p. 121 - 127
  作者：Pave, Gregoire、Chalard, Pierre、Viaud-Massuard, Marie-Claude、Troin, Yves、Guillaumet, Gerald

  DOI：——

  日期：——