2-(Z)-triisopropylsilylmethylidene-4-phenyl-8-phenyl-2H-1,4-benzoxazin-3(4H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-(Z)-triisopropylsilylmethylidene-4-phenyl-8-phenyl-2H-1,4-benzoxazin-3(4H)-one
• 英文别名: (2Z)-4,8-diphenyl-2-[tri(propan-2-yl)silylmethylidene]-1,4-benzoxazin-3-one
• 化学式: C₃₀H₃₅NO₂Si
• 分子量: 469.699
• InChiKey: PVURPHFZHBQWFE-RRAHZORUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.51
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-biphenyl triisopropylsilylethynyl ether 、 异氰酸苯酯 在 zinc diacetate 、 palladium diacetate 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以64%的产率得到2-(Z)-triisopropylsilylmethylidene-4-phenyl-8-phenyl-2H-1,4-benzoxazin-3(4H)-one
  参考文献：
  名称：

  Palladium-catalyzed annulation of alkynyl aryl ethers with isocyanates through o-C–H cleavage. Synthesis of solid-state emissive 2-methylidene-2H-1,4-benzoxazin-3(4H)-ones

  摘要：

  The title transformation can be achieved by the o-C-H cleavage of allcynyl aryl ethers, which is easily derived from phenols, followed by the insertion/annulation with isocyanates in the presence of a palladium catalyst. Various alkynyl aryl ethers and arylisocyanates are applied to this transformation to give the corresponding cyclic products. Mechanistic study indicates that the C-H cleavage is effected reversibly by the concerted metalation-deprotonation pathway. The products exhibit solid-state luminescence upon irradiation of UV light. Fluorescent maxima and quantum yields can be controlled by the substituents at appropriate sites in the products. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.062

文献信息

• Palladium-catalyzed annulation of alkynyl aryl ethers with isocyanates through o-C–H cleavage. Synthesis of solid-state emissive 2-methylidene-2H-1,4-benzoxazin-3(4H)-ones
  作者：Yasunori Minami、Mayuko Kanda、Megumi Sakai、Tamejiro Hiyama

  DOI：10.1016/j.tet.2015.02.062

  日期：2015.7

  The title transformation can be achieved by the o-C-H cleavage of allcynyl aryl ethers, which is easily derived from phenols, followed by the insertion/annulation with isocyanates in the presence of a palladium catalyst. Various alkynyl aryl ethers and arylisocyanates are applied to this transformation to give the corresponding cyclic products. Mechanistic study indicates that the C-H cleavage is effected reversibly by the concerted metalation-deprotonation pathway. The products exhibit solid-state luminescence upon irradiation of UV light. Fluorescent maxima and quantum yields can be controlled by the substituents at appropriate sites in the products. (C) 2015 Elsevier Ltd. All rights reserved.