4-amino-2-cyclohexyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide | 106350-12-3

• 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: 4-amino-2-cyclohexyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide
• 英文别名: 4-Amino-2-cyclohexyl-3-oxo-2,3-dihydro-1,2,5-thiadiazole 1,1-di-oxide；4-amino-2-cyclohexyl-1,1-dioxo-1,2,5-thiadiazol-3-one
• CAS: 106350-12-3
• 化学式: C₈H₁₃N₃O₃S
• 分子量: 231.276
• InChiKey: ZDIONSUMNACEOW-UHFFFAOYSA-N

物化性质

• 熔点：
  164-166 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  386.8±25.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-2-cyclohexyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 2.5h， 生成 potassium 2-amino-2-[(N-cyclohexylsulfamoyl)imino]acetate
  参考文献：
  名称：

  Kinetics of the hydrolysis of cyclicN-substituted sulfamides: 4-amino-2-cyclohexyl- and 4-amino-2-phenethyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxides

  摘要：

  The hydrolysis reactions of 4-amino-2-phenethyl- and 4-amino-2-cyclohexyl-2,3-dihydro-3-oxo-1,2,5 thiadiazole 1,1-dioxide (Ia and Ib) were investigated in the range 24-73 degrees C in buffered aqueous solutions. The observed rate constants (k(obs)) are independent of pH in the range ca 1-4 pH, but increase with increase in pH above ca 4. A linear log k(obs) vs pH profile with unit slope is observed from pH ca 4 up to the highest experimental pH (ca 10). The products are the corresponding new compounds: 2-amino-2-[(N-substituted-sulfamoyl)imino]acetic acid salts. The C=N bond of these compounds hydrolyses further, in a slow reaction, to the sulfamide and oxalic acid derivatives. The substrates decompose to the final products without accumulation of the acetic acid derivatives under these experimental conditions. A mechanism is proposed. Rate constants and activation parameters are given for the first reaction step. Owing to steric effects, the reaction rate is higher for the N-phenethyl-substituted derivative than for the 2-cyclohexyl-substituted derivative. (C) 1998 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199807)11:7<489::aid-poc29>3.0.co;2-g
• 作为产物：
  描述：

  3,4-Diamino-2-cyclohexyl-1,1-dioxo-1H-1λ6-[1,2,5]thiadiazol-2-ium; chloride 在 盐酸 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 生成 4-amino-2-cyclohexyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxide
  参考文献：
  名称：

  Alkorta, Ibon; Aran, Vicente J.; Davila, Elena, Liebigs Annalen der Chemie, 1989, p. 1135 - 1138

  摘要：

  DOI：

文献信息

• Aran; Davila; Frances, Arzneimittel-Forschung/Drug Research, 1990, vol. 40, # 9, p. 1003 - 1007
  作者：Aran、Davila、Frances、Goya、Gras、Martinez、Mylonakis、Pardo

  DOI：——

  日期：——
• Aran, Vicente J.; Bielsa, Agustin G.; Ruiz, Jose R., Journal of the Chemical Society. Perkin transactions I, 1986, p. 643 - 646
  作者：Aran, Vicente J.、Bielsa, Agustin G.、Ruiz, Jose R.、Stud, Manfred

  DOI：——

  日期：——
• ARAN, V. J.;BIELSA, A. G.;RUIZ, J. R.;STUD, M., J. CHEM. SOC. PERKIN TRANS., 1986, N 4, 643-645
  作者：ARAN, V. J.、BIELSA, A. G.、RUIZ, J. R.、STUD, M.

  DOI：——

  日期：——
• Alkorta, Ibon; Aran, Vicente J.; Davila, Elena, Liebigs Annalen der Chemie, 1989, p. 1135 - 1138
  作者：Alkorta, Ibon、Aran, Vicente J.、Davila, Elena、Ruiz, Jose R.、Stud, Manfred

  DOI：——

  日期：——
• Kinetics of the hydrolysis of cyclicN-substituted sulfamides: 4-amino-2-cyclohexyl- and 4-amino-2-phenethyl-2,3-dihydro-3-oxo-1,2,5-thiadiazole 1,1-dioxides
  作者：M. F. Rozas、E. L. Svartman、M. V. Mir�fico、E. J. Vasini

  DOI：10.1002/(sici)1099-1395(199807)11:7<489::aid-poc29>3.0.co;2-g

  日期：1998.7

  The hydrolysis reactions of 4-amino-2-phenethyl- and 4-amino-2-cyclohexyl-2,3-dihydro-3-oxo-1,2,5 thiadiazole 1,1-dioxide (Ia and Ib) were investigated in the range 24-73 degrees C in buffered aqueous solutions. The observed rate constants (k(obs)) are independent of pH in the range ca 1-4 pH, but increase with increase in pH above ca 4. A linear log k(obs) vs pH profile with unit slope is observed from pH ca 4 up to the highest experimental pH (ca 10). The products are the corresponding new compounds: 2-amino-2-[(N-substituted-sulfamoyl)imino]acetic acid salts. The C=N bond of these compounds hydrolyses further, in a slow reaction, to the sulfamide and oxalic acid derivatives. The substrates decompose to the final products without accumulation of the acetic acid derivatives under these experimental conditions. A mechanism is proposed. Rate constants and activation parameters are given for the first reaction step. Owing to steric effects, the reaction rate is higher for the N-phenethyl-substituted derivative than for the 2-cyclohexyl-substituted derivative. (C) 1998 John Wiley & Sons, Ltd.