乙基3-氨基-5-(甲基氨基)-1,2-噻唑-4-羧酸酯 | 117377-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 乙基3-氨基-5-(甲基氨基)-1,2-噻唑-4-羧酸酯
• 英文名称: ethyl 3-amino-5-(N-methylamino)isothiazole-4-carboxylate
• 英文别名: 3-amino-5-(methylamino)isothiazole-4-carboxylic acid ethyl ester；Ethyl 3-amino-5-(methylamino)isothiazole-4-carboxylate；ethyl 3-amino-5-(methylamino)-1,2-thiazole-4-carboxylate
• CAS: 117377-37-4
• 化学式: C₇H₁₁N₃O₂S
• 分子量: 201.249
• InChiKey: UUKTWZRERZBRIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙基3-氨基-5-(甲基氨基)-1,2-噻唑-4-羧酸酯 在 氢氧化钾 作用下， 反应 0.5h， 以93%的产率得到3-amino-5-(N-methylamino)isothiazole-4-carboxylic acid
  参考文献：
  名称：

  The Synthesis of Substituted Imidazo[4,5-d]isothiazoles via the Ring Annulation of Isothiazole Diamines: An Investigation of the Chemical, Physical, and Biological Properties of Several Novel 5:5 Fused Analogs of the Purine Ring System

  摘要：

  A series of imidazo[4,5-d]isothiazoles have been prepared from isothiazole precursors via a strategy employing ring annulation of the appropriate isothiazole diamine. In this manner, several 4,5-diaminoisothiazoles were converted into the corresponding 5-(alkylthio)imidazo[4,5-d]isothiazoles via a two-step, one-pot procedure in good yield. This methodology proved quite general and allows for the introduction of various substituents onto the 3-, 5-, and 6-positions of this ring system. Reaction with Raney nickel destroyed the ring system, presumably through removal of the sulfur at the 1-position, and the 5-mercapto substituent could not be removed selectively. Ring annulation with diethoxymethyl acetate provided the 5-unsubstituted imidazo[4,5-d]isothiazoles but was less general, and only the 3-methyl derivatives could be prepared. Imidazo[4,5-d]isothiazoles bearing no substituents on nitrogen readily underwent alkylation to afford mixtures of the N-4- and N-6-substituted compounds. The chemical and physical properties of these novel heterocycles were studied in detail, and the structure of 3-methyl-5-methanesulfonyl-6-(phenylmethyl)imidazo[4,5-d] isothiazole was verified by single crystal X-ray diffraction studies.

  DOI：

  10.1021/jo00125a016
• 作为产物：
  描述：

  异硫氰酸甲酯 、 氰乙酸乙酯 在 氯胺 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以60%的产率得到乙基3-氨基-5-(甲基氨基)-1,2-噻唑-4-羧酸酯
  参考文献：
  名称：

  Shishoo, C. J.; Devani, M. B.; Ananthan, S., Journal of Heterocyclic Chemistry, 1988, vol. 25, # 2, p. 759 - 765

  摘要：

  DOI：

文献信息

• SHISHOO, C. J.;DEVANI, M. B.;ANANTHAN, S.;BHADTI, V. S.;ULLAS, G. V., J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 759-765
  作者：SHISHOO, C. J.、DEVANI, M. B.、ANANTHAN, S.、BHADTI, V. S.、ULLAS, G. V.

  DOI：——

  日期：——