2-(1,3-benzothiazol-2-yl)-3-ethyl-thiazolo[3,2-a]pyrimidin-4-one | 918891-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(1,3-benzothiazol-2-yl)-3-ethyl-thiazolo[3,2-a]pyrimidin-4-one
• 英文别名: 7-(1,3-Benzothiazol-2-yl)-6-ethyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one；7-(1,3-benzothiazol-2-yl)-6-ethyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one
• CAS: 918891-47-1
• 化学式: C₁₅H₁₁N₃OS₂
• 分子量: 313.404
• InChiKey: KDRYTRCPLPSWCM-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238 °C(Solvent: Ligroine)
• 沸点：
  486.9±55.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  99.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯并噻唑-2-甲醛 在 palladium diacetate 4 A molecular sieve 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 100.0 ℃ 、2.76 MPa 条件下， 反应 24.0h， 生成 2-(1,3-benzothiazol-2-yl)-3-ethyl-thiazolo[3,2-a]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and isomerization of N-α-aza-heteroaryl-β-lactams

  摘要：

  The [2+2] carbonylative cycloaddition of N-cx-aza-heteroaryl substituted imines with allyl bromide led partially to beta-lactams, which underwent isomerization to the more stable alpha,beta-unsaturated carbonyl compound. Pyrimidinone derivatives together with doubly unsaturated amides represent the remaining isolated products. The strong electron-withdrawing effect of the two alpha-aza-heterocycles linked to the nitrogen atom and to the C4 of the 2-azetidinone structure could give a ring expansion, through a 2-azetinone intermediate that affords the pyrimidinone compounds. The substituted amides, instead, should result from a ring-opening reaction of the beta-lactam. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.075

文献信息

• Synthesis and isomerization of N-α-aza-heteroaryl-β-lactams
  作者：Luigino Troisi、Ludovico Ronzini、Catia Granito、Emanuela Pindinelli、Alessandro Troisi、Tullio Pilati

  DOI：10.1016/j.tet.2006.09.075

  日期：2006.12

  The [2+2] carbonylative cycloaddition of N-cx-aza-heteroaryl substituted imines with allyl bromide led partially to beta-lactams, which underwent isomerization to the more stable alpha,beta-unsaturated carbonyl compound. Pyrimidinone derivatives together with doubly unsaturated amides represent the remaining isolated products. The strong electron-withdrawing effect of the two alpha-aza-heterocycles linked to the nitrogen atom and to the C4 of the 2-azetidinone structure could give a ring expansion, through a 2-azetinone intermediate that affords the pyrimidinone compounds. The substituted amides, instead, should result from a ring-opening reaction of the beta-lactam. (c) 2006 Elsevier Ltd. All rights reserved.