ethyl 3-oxo-1,4-thiazine-5-carboxylate | 3585-97-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-oxo-1,4-thiazine-5-carboxylate
• 英文别名: 5-Ethoxycarbonyl-2,3-dihydro-4H-1,4-thiazin-3-on；5-oxo-5,6-dihydro-4H-[1,4]thiazine-3-carboxylic acid ethyl ester；ethyl 5-oxo-4H-1,4-thiazine-3-carboxylate
• CAS: 3585-97-5
• 化学式: C₇H₉NO₃S
• 分子量: 187.219
• InChiKey: IPZKFLPJRCNMMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-oxo-1,4-thiazine-5-carboxylate 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 6.0h， 生成 ethyl 4-(2-deoxy-β-D-erythro-pentofuranosyl)-3-oxo-1,4-thiazine-5-carboxylate
  参考文献：
  名称：

  Nucleosides of 1,4-thiazin-3-one and derivatives as tetrahedral intermediate analogs of enzymes in pyrimidine nucleoside metabolism

  摘要：

  Reaction of the trimethylsilylated derivative of 1,4-thiazin-3-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose in the presence of SnCl4 gave, after deblocking, 4-beta-ribofuranosyl-1,4-thiazin-3-one (8). Treatment of 1,4-thiazin-3-one with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose in the presence of sodium hydride provided, after deblocking, the corresponding 2-deoxy-beta-D-ribofuranosyl derivatives (19). Oxidation of 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one (7) with 1 equiv of m-chloroperbenzoic acid resulted in 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazine-2,3-dione (9) and 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one 1-oxide (10). Evidence is presented that indicates that the oxidation of the thiazine at the 2-position is due to a Pummerere rearrangement. The new compounds failed to show significant activity against tumor cell lines in culture, L1210 cells in vivo, virus cytotoxicity in cell culture, or cytidine deaminase.

  DOI：

  10.1021/jm00403a015
• 作为产物：
  描述：

  ethyl 2-azidoacrylate 在 乙醇锂 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 ethyl 3-oxo-1,4-thiazine-5-carboxylate
  参考文献：
  名称：

  2-叠氮丙酸乙酯与亲核试剂的反应

  摘要：

  在乙醇中分别用苯硫酚或乙醇钠（或锂）处理后，将标题化合物转化为具有 3-苯硫基或 3-乙氧基取代基的 2-氨基丙烯酸乙酯。还讨论了与巯基乙酸乙酯的反应。

  DOI：

  10.1246/cl.1982.527

文献信息

• KAKIMOTO, MASA-AKI;KAI, MARIKO;KONDO, KIYOSI;HIYAMA, TAMEJIRO, CHEM. LETT., 1982, N 4, 527-528
  作者：KAKIMOTO, MASA-AKI、KAI, MARIKO、KONDO, KIYOSI、HIYAMA, TAMEJIRO

  DOI：——

  日期：——
• Nucleosides of 1,4-thiazin-3-one and derivatives as tetrahedral intermediate analogs of enzymes in pyrimidine nucleoside metabolism
  作者：E. Ted Marcus、Afaf Gundy、Corey H. Levenson、Rich B. Meyer

  DOI：10.1021/jm00403a015

  日期：1988.8

  Reaction of the trimethylsilylated derivative of 1,4-thiazin-3-one with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose in the presence of SnCl4 gave, after deblocking, 4-beta-ribofuranosyl-1,4-thiazin-3-one (8). Treatment of 1,4-thiazin-3-one with 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-alpha-D-erythro-pentofuranose in the presence of sodium hydride provided, after deblocking, the corresponding 2-deoxy-beta-D-ribofuranosyl derivatives (19). Oxidation of 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one (7) with 1 equiv of m-chloroperbenzoic acid resulted in 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazine-2,3-dione (9) and 4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,4-thiazin-3-one 1-oxide (10). Evidence is presented that indicates that the oxidation of the thiazine at the 2-position is due to a Pummerere rearrangement. The new compounds failed to show significant activity against tumor cell lines in culture, L1210 cells in vivo, virus cytotoxicity in cell culture, or cytidine deaminase.
• REACTION OF ETHYL 2-AZIDOPROPENOATE WITH NUCLEOPHILES
  作者：Masa-aki Kakimoto、Mariko Kai、Kiyosi Kondo、Tamejiro Hiyama

  DOI：10.1246/cl.1982.527

  日期：1982.4.5

  The title compound is transformed into ethyl 2-aminopropenoate having 3-phenylthio or 3-ethoxy substituent upon treatment with thiophenol or sodium (or lithium) ethoxide in ethanol, respectively. The reaction with ethyl mercaptoacetate is also discussed.

  在乙醇中分别用苯硫酚或乙醇钠（或锂）处理后，将标题化合物转化为具有 3-苯硫基或 3-乙氧基取代基的 2-氨基丙烯酸乙酯。还讨论了与巯基乙酸乙酯的反应。