4-piperidino-1,3-benzoxazin-2-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: 4-piperidino-1,3-benzoxazin-2-one
• 英文别名: 4-Piperidin-1-yl-1,3-benzoxazin-2-one
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: TWTXAVLIGMDCSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(2-hydroxythiobenzoyl)morpholine 、 silver cyanate 以 乙腈 为溶剂， 以94%的产率得到4-piperidino-1,3-benzoxazin-2-one
  参考文献：
  名称：

  Silver Ion-mediated Desulfurization of N,N-Disubstituted 2-Hydroxythiobenzamides

  摘要：

  Silver ion-mediated desulfurization of N-(2-hydroxythiobenzoyl)morpholine (1a) or -piperidine (1b) was used to develop a new synthetic method for heterocycles such as 1,3-benzoxazin-1-ium salts. 2-Amino-4-morpholino- and 2-amino-4-piperidino-1,3-benzoxazin-1-ium perchlorate (2a, 2b) or 2-(NN-dimethylamino)-4-morpholino- and 2-(N,N-dimethylamino)-4-piperidino-1,3-benzoxazin-1-ium perchlorate (3a, 3b) were obtained by treatment of la and 1b, respectively, with silver perchlorate in the presence of excess cyanamide or N,N-dimethylcyanamide, and the structure of 3a was confirmed by X-Ray crystallography. Desulfurization of 1 with AgOCN afforded 1,3-benzoxazin-2-ones (4). In addition, treatment of 1 with methyl cyanoacetate in the presence of silver trifluoroacetate and triethylamine gave 3-cyanochromen-2-ones (5).

  DOI：

  10.3987/com-01-9396

文献信息

• Silver Ion-mediated Desulfurization of N,N-Disubstituted 2-Hydroxythiobenzamides
  作者：Isao Shibuya、Kazumasa Honda、Yasuo Gama、Masao Shimizu

  DOI：10.3987/com-01-9396

  日期：——

  Silver ion-mediated desulfurization of N-(2-hydroxythiobenzoyl)morpholine (1a) or -piperidine (1b) was used to develop a new synthetic method for heterocycles such as 1,3-benzoxazin-1-ium salts. 2-Amino-4-morpholino- and 2-amino-4-piperidino-1,3-benzoxazin-1-ium perchlorate (2a, 2b) or 2-(NN-dimethylamino)-4-morpholino- and 2-(N,N-dimethylamino)-4-piperidino-1,3-benzoxazin-1-ium perchlorate (3a, 3b) were obtained by treatment of la and 1b, respectively, with silver perchlorate in the presence of excess cyanamide or N,N-dimethylcyanamide, and the structure of 3a was confirmed by X-Ray crystallography. Desulfurization of 1 with AgOCN afforded 1,3-benzoxazin-2-ones (4). In addition, treatment of 1 with methyl cyanoacetate in the presence of silver trifluoroacetate and triethylamine gave 3-cyanochromen-2-ones (5).