4-oxo-4H-3,1-benzothiazine-2-carbonitrile | 169778-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 4-oxo-4H-3,1-benzothiazine-2-carbonitrile
• 英文别名: 2-cyano-3,1-benzothiazin-4-one；4-Oxo-3,1-benzothiazine-2-carbonitrile
• CAS: 169778-86-3
• 化学式: C₉H₄N₂OS
• 分子量: 188.21
• InChiKey: QMLPGEAOHZZDIL-UHFFFAOYSA-N

物化性质

• 沸点：
  375.4±25.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-Dimethylhydrazine dihydrochloride 、 4-oxo-4H-3,1-benzothiazine-2-carbonitrile 在 三乙胺 作用下， 以 吡啶 为溶剂， 反应 0.17h， 以55%的产率得到2-(1,2-dimethylhydrazino)-4H-3,1-benzoxazine-4-thione
  参考文献：
  名称：

  Synthesis of novel 1,3,4-benzotriazepine derivatives from 4-oxo-3,1-benzoxazine and 3,1-benzothiazine-2-carbonitriles

  摘要：

  Synthesis of novel oxygen and sulfur containing 1,3,4-benzotriazepine derivatives was performed via 3,1-benz-oxazine and 3,1-benzothiazine intermediates obtained from Appel's salt chemistry. We observed that the sulfur containing precursors reacted differently than their oxygenated congeners and, after rearrangement, afforded novel heterocyclic compounds (e.g., benzoxazin-4-thione and 2-cyanoy 1,3,4-triazepine). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.023
• 作为产物：
  描述：

  N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-anthranilic acid 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到4-oxo-4H-3,1-benzothiazine-2-carbonitrile
  参考文献：
  名称：

  3,1-Benzoxazin-4-ones, 3,1-benzothiazin-4-ones and N-arylcyanothioformamides

  摘要：

  氨基苯甲酸和4,5-二氯-1,2,3-二噻唑鎓盐1反应生成精细的二噻唑亚氨基羧酸8，该化合物在温和热解后生成2-氰基-3,1-苯并噁唑啉-4-酮6，与三苯基膦反应生成2-氰基-3,1-苯并噻唑啉-4-酮7，均为定量产物；一般来说，N-芳基亚氨基二噻唑类化合物2与三苯基膦反应生成相应的氰基噻唑酰胺3，为从苯胺合成这些化合物提供了两步温和反应的途径。

  DOI：

  10.1039/c39950001419

文献信息

• 3,1-Benzoxazin-4-ones, 3,1-benzothiazin-4-ones and N-arylcyanothioformamides
  作者：Thierry Besson、Kumaraswamy Emayan、Charles W. Rees

  DOI：10.1039/c39950001419

  日期：——

  Anthranilic acid and 4,5-dichloro-1,2,3-dithiazolium chloride 1 give the delicate dithiazoloimino carboxylic acid 8 which on mild thermolysis gives 2-cyano-3,1-benzoxazin-4-one 6 and with triphenylphosphine gives 2-cyano-3,1-benzothiazin-4-one 7, both quantitatively; in general N-aryliminodithiazoles 2 with triphenylphosphine give the corresponding cyanothioformanilides 3, providing a route to these compounds from anilines in two mild steps.

  氨基苯甲酸和4,5-二氯-1,2,3-二噻唑鎓盐1反应生成精细的二噻唑亚氨基羧酸8，该化合物在温和热解后生成2-氰基-3,1-苯并噁唑啉-4-酮6，与三苯基膦反应生成2-氰基-3,1-苯并噻唑啉-4-酮7，均为定量产物；一般来说，N-芳基亚氨基二噻唑类化合物2与三苯基膦反应生成相应的氰基噻唑酰胺3，为从苯胺合成这些化合物提供了两步温和反应的途径。
• Besson, Thierry; Emayan, Kumaraswamy; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1995, # 17, p. 2097 - 2102
  作者：Besson, Thierry、Emayan, Kumaraswamy、Rees, Charles W.

  DOI：——

  日期：——
• Antimicrobial evaluation of 3,1-benzoxazin-4-ones, 3,1-benzothiazin-4-ones, 4-alkoxyquinazolin-2-carbonitriles and N-arylimino-1,2,3-dithiazoles
  作者：Thierry Besson、Charles W. Rees、Gilles Cottenceau、Anne-Marie Pons

  DOI：10.1016/0960-894x(96)00423-4

  日期：1996.10

  Novel 3,1-benzoxazinones, 3,1-benzothiazinones and 4-alkoxyquinazolines have been synthesized via N-aryl-1,2,3-dithiazoles derivatives. The antibacterial and antifungal activity of these compounds were measured; the dithiazoles are significantly active against fungi. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of novel 1,3,4-benzotriazepine derivatives from 4-oxo-3,1-benzoxazine and 3,1-benzothiazine-2-carbonitriles
  作者：François-René Alexandre、Amaya Berecibar、Roger Wrigglesworth、Laurence Perreux、Jean Guillon、Jean-Michel Léger、Valérie Thiéry、Thierry Besson

  DOI：10.1016/j.tet.2005.06.023

  日期：2005.8

  Synthesis of novel oxygen and sulfur containing 1,3,4-benzotriazepine derivatives was performed via 3,1-benz-oxazine and 3,1-benzothiazine intermediates obtained from Appel's salt chemistry. We observed that the sulfur containing precursors reacted differently than their oxygenated congeners and, after rearrangement, afforded novel heterocyclic compounds (e.g., benzoxazin-4-thione and 2-cyanoy 1,3,4-triazepine). (c) 2005 Elsevier Ltd. All rights reserved.