3-chloro-4-ethoxy-[1,2,5]thiadiazole | 5728-17-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-4-ethoxy-[1,2,5]thiadiazole
• 英文别名: 3-Chloro-4-ethoxy-1,2,5-thiadiazole
• CAS: 5728-17-6
• 化学式: C₄H₅ClN₂OS
• 分子量: 164.615
• InChiKey: QLHSAELBBONESC-UHFFFAOYSA-N

物化性质

• 沸点：
  86.5-87.5 °C(Press: 17 Torr)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-4-ethoxy-[1,2,5]thiadiazole 、 磺胺 在 乙酰胺 、 potassium carbonate 作用下， 生成 N'-<3-Aethoxy-1.2.5-thiadiazol-4-yl>-sulfanilamid
  参考文献：
  名称：

  General synthetic system for 1,2,5-thiadiazoles

  摘要：

  DOI：

  10.1021/jo01284a040
• 作为产物：
  描述：

  Cyan-imidoameisensaeureethylester 在 二氯化二硫 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-chloro-4-ethoxy-[1,2,5]thiadiazole
  参考文献：
  名称：

  General synthetic system for 1,2,5-thiadiazoles

  摘要：

  DOI：

  10.1021/jo01284a040

文献信息

• 1,2,5-Thiadiazole Analogues of Aceclidine as Potent m₁ Muscarinic Agonists
  作者：John S. Ward、Leander Merritt、David O. Calligaro、Franklin P. Bymaster、Harlan E. Shannon、Charles H. Mitch、Celia Whitesitt、David Brunsting、Malcolm J. Sheardown、Preben H. Olesen、Michael D. B. Swedberg、Lone Jeppesen、Per Sauerberg

  DOI：10.1021/jm970125n

  日期：1998.1.1

  The acetyl group of the muscarinic agonist aceclidine 4 was replaced by various 1,2,5-thiadiazoles to provide a new series of potent m(1) muscarinic agonists 17 and 18. Optimal mi muscarinic agonist potency was achieved when the 1,2,g-thiadiazole substituent was either a butyloxy, 17d, or butylthio, 18d, group. Although 1,2,5-oxadiazole 37 and pyrazine 39 are iso-pi-electronic with 1,2,5-thiadiazole 17d, both analogues were substantially less active than 17d. Compounds with high muscarinic affinity and/or m(1) muscarinic agonist efficacy were also obtained when the 3-oxyquinuclidine moiety of 17d or 18c was replaced by ethanolamines, hydroxypyrrolidines, hydroxyazetidine, hydroxyisotropanes, or hydroxyazanorbornanes. The structure-activity data support the participation of the oxygen or sulfur atom in the substituent on the 1,2,5-thiadiazole in the activation of the m(1) receptor. Several of these new 1,2,5-thiadiazoles have m(1) agonist efficacy, potency, and selectivity comparable to those of xanomeline 2 in the muscarinic tests investigated.
• General synthetic system for 1,2,5-thiadiazoles
  作者：Leonard M. Weinstock、Paul Davis、Barry Handelsman、Roger J. Tull

  DOI：10.1021/jo01284a040

  日期：1967.9