2,4-二甲基-4,5-二氢-1,3-噻唑 | 6114-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 2,4-二甲基-4,5-二氢-1,3-噻唑
• 英文名称: 2,4-dimethyl-4,5-dihydro-1,3-thiazole
• 英文别名: 2,4-dimethyl-4,5-dihydro-thiazole；2,4-dimethyl-2-thiazoline；2,4-Dimethyl-Δ²-thiazolin；2,4-Dimethyl-Λ2-thiazolin；2,4-Dimethyl-2-thiazolin
• CAS: 6114-40-5
• 化学式: C₅H₉NS
• mdl: MFCD01105109
• 分子量: 115.199
• InChiKey: DGGUAAPXUKWYNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二甲基-4,5-二氢-1,3-噻唑 以 乙腈 为溶剂， 生成 N-allylthioacetamide
  参考文献：
  名称：

  光致反应—LXXIX：2-噻唑啉的光化学

  摘要：

  在2537Å的光照射下，2-烷基-2-噻唑啉（1）重排为主要途径的N-烯基硫酰胺（2和3），并碎裂为次要的腈和环硫化物。为中间形成价键异构体N-硫代酰基氮丙啶提供了证据，然后将其光化学转化为N-烯基硫代酰胺。

  DOI：

  10.1016/0040-4020(75)80164-5
• 作为产物：
  描述：

  2-acetylaminopropan-1-ol 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以46%的产率得到2,4-二甲基-4,5-二氢-1,3-噻唑
  参考文献：
  名称：

  Design and Synthesis of Soluble and Cell-Permeable PI3Kδ Inhibitors for Long-Acting Inhaled Administration

  摘要：

  PI3K delta is a lipid kinase that is believed to be important in the migration and activation of cells of the immune system. Inhibition is hypothesized to provide a powerful yet selective immunomodulatory effect that may be beneficial for the treatment of conditions such as asthma or rheumatoid arthritis. In this work, we describe the identification of inhibitors based on a thiazolopyridone core structure and their subsequent optimization for inhalation: The initially identified compound (13) had good potency and isoform selectivity but was not suitable for inhalation. Addition of basic substituents to a region of the molecule pointing to solvent was tolerated (enzyme inhibition pIC(50) > 9), and by careful manipulation, of the pK(a) and lipophilicity, we were able to discover compounds (20b, 20f) with good lung retention and cell potency that could be taken forward to in vivo studies where significant target engagement could be demonstrated.

  DOI：

  10.1021/acs.jmedchem.7b00401

文献信息

• Beger,J. et al., Journal fur praktische Chemie (Leipzig 1954), 1969, vol. 311, p. 408 - 419
  作者：Beger,J. et al.

  DOI：——

  日期：——
• Process for the preparation of thiazoles
  申请人：LEUNA WERKE VEB

  公开号：US02870158A1

  公开（公告）日：1959-01-20