5-benzylsulfanyl-2,4-dihydro-[1,2,4]triazol-3-one | 65479-47-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-benzylsulfanyl-2,4-dihydro-[1,2,4]triazol-3-one
• 英文别名: 5-(benzylsulfanyl)-4H-1,2,4-triazol-3-ol；3-benzylsulfanyl-1,4-dihydro-1,2,4-triazol-5-one
• CAS: 65479-47-2
• 化学式: C₉H₉N₃OS
• 分子量: 207.256
• InChiKey: XOLVXBSCXULQJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-benzylsulfanyl-2,4-dihydro-[1,2,4]triazol-3-one 在 双氧水 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 40.0h， 生成 5-Phenylmethanesulfonyl-2,4-dihydro-[1,2,4]triazol-3-one
  参考文献：
  名称：

  A unified approach to systematic isosteric substitution for acidic groups and application to NMDA antagonists related to 2-amino-7-phosphonoheptanoate

  摘要：

  A systematic approach to the replacement of acidic groups with potential bioisosteres is described. The strategy involves simple nucleophilic displacement of a common alkyl halide precursor with a variety of mercaptoazoles and related molecules. The mercaptoazoles and their oxidized derivatives (sulfinyl- and sulfonylazoles) represent a series of possible surrogates for acidic groups which span a pKa range from about 4.5-11.5. This simple strategy was extended to include 2-hydroxy- or 2-aminothiophenyl groups which function as relatively nonacidic isosteres for a phosphonic acid. By replacing the phosphonic acid of 2-amino-7-phosphonoheptanoate (AP-7) with these groups, we have synthesized novel N-methyl-d-aspartate (NMDA) antagonists.

  DOI：

  10.1021/jm00165a030
• 作为产物：
  描述：

  3-benzylsulfanylcarboximidoyl-carbazic acid ethyl ester 在 alkaline solution 作用下， 生成 5-benzylsulfanyl-2,4-dihydro-[1,2,4]triazol-3-one
  参考文献：
  名称：

  Fromm; Nehring, Chemische Berichte, 1923, vol. 56, p. 1374

  摘要：

  DOI：

文献信息

• ESMAIL R.; KURZER F., TETRAHEDRON <TETR-AB>, 1977, 33, NO 15, 2007-2012
  作者：ESMAIL R.、 KURZER F.

  DOI：——

  日期：——
• KURZER F.; SECKER J. L., TETRAHEDRON<TETR-AB>, 1977, 33, NO 15, 1999-2006
  作者：KURZER F.、 SECKER J. L.

  DOI：——

  日期：——
• Fromm; Nehring, Chemische Berichte, 1923, vol. 56, p. 1374
  作者：Fromm、Nehring

  DOI：——

  日期：——
• A unified approach to systematic isosteric substitution for acidic groups and application to NMDA antagonists related to 2-amino-7-phosphonoheptanoate
  作者：B. L. Chenard、C. A. Lipinski、B. W. Dominy、E. E. Mena、R. T. Ronau、G. C. Butterfield、L. C. Marinovic、M. Pagnozzi、T. W. Butler、T. Tsang

  DOI：10.1021/jm00165a030

  日期：1990.3

  A systematic approach to the replacement of acidic groups with potential bioisosteres is described. The strategy involves simple nucleophilic displacement of a common alkyl halide precursor with a variety of mercaptoazoles and related molecules. The mercaptoazoles and their oxidized derivatives (sulfinyl- and sulfonylazoles) represent a series of possible surrogates for acidic groups which span a pKa range from about 4.5-11.5. This simple strategy was extended to include 2-hydroxy- or 2-aminothiophenyl groups which function as relatively nonacidic isosteres for a phosphonic acid. By replacing the phosphonic acid of 2-amino-7-phosphonoheptanoate (AP-7) with these groups, we have synthesized novel N-methyl-d-aspartate (NMDA) antagonists.