(Z)-3-butylamino-1-(1H-1-imidazolyl)-4-methyl-2-penten-1-one | 217473-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-3-butylamino-1-(1H-1-imidazolyl)-4-methyl-2-penten-1-one
• 英文别名: (Z)-3-(butylamino)-1-imidazol-1-yl-4-methylpent-2-en-1-one
• CAS: 217473-26-2
• 化学式: C₁₃H₂₁N₃O
• 分子量: 235.329
• InChiKey: HJOJULVNKGHRHA-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  烯丙硫醇 、 (Z)-3-butylamino-1-(1H-1-imidazolyl)-4-methyl-2-penten-1-one 在 sodium prop-2-ene-1-thiolate 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到S-prop-2-enyl (Z)-3-(butylamino)-4-methylpent-2-enethioate
  参考文献：
  名称：

  Synthesis and Reactivity of New β-Enamino Acid Derivatives:  A Simple and General Approach to β-Enamino Esters and Thioesters

  摘要：

  A new strategy has been developed for the synthesis of several beta-enamino acid derivatives. N,N'-Carbonyldiimidazole has been used as C-acylating agent of methyl ketimines, providing a direct and simple route to new beta-enamino carbonyl imidazole derivatives 2. These derivatives 2 were cleanly and efficiently transformed into beta-enamino esters 4 (X = O) and thioesters 4 (X = S) by reaction with a great variety of alcohols and thiols, including tertiary ones. Alternative and complementary routes to compounds 4 were also investigated. In addition, beta-keto esters 6 have been obtained by mild acid hydrolysis of beta-enamino esters 4.

  DOI：

  10.1021/jo9809480
• 作为产物：
  描述：

  3-methyl-N-propylbutan-2-imine 、 N,N'-羰基二咪唑 在 三氟化硼乙醚 作用下， 生成 (Z)-3-butylamino-1-(1H-1-imidazolyl)-4-methyl-2-penten-1-one
  参考文献：
  名称：

  Synthesis and Reactivity of New β-Enamino Acid Derivatives:  A Simple and General Approach to β-Enamino Esters and Thioesters

  摘要：

  A new strategy has been developed for the synthesis of several beta-enamino acid derivatives. N,N'-Carbonyldiimidazole has been used as C-acylating agent of methyl ketimines, providing a direct and simple route to new beta-enamino carbonyl imidazole derivatives 2. These derivatives 2 were cleanly and efficiently transformed into beta-enamino esters 4 (X = O) and thioesters 4 (X = S) by reaction with a great variety of alcohols and thiols, including tertiary ones. Alternative and complementary routes to compounds 4 were also investigated. In addition, beta-keto esters 6 have been obtained by mild acid hydrolysis of beta-enamino esters 4.

  DOI：

  10.1021/jo9809480