4-benzyl 1-tert-butyl (S)-2-methyl-1,4-diazepane-1,4-dicarboxylate | 1411975-64-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzyl 1-tert-butyl (S)-2-methyl-1,4-diazepane-1,4-dicarboxylate
• 英文别名: 4-benzyl 1-(tert-butyl) (S)-2-methyl-1,4-diazepane-1,4-dicarboxylate；4-O-benzyl 1-O-tert-butyl (2S)-2-methyl-1,4-diazepane-1,4-dicarboxylate
• CAS: 1411975-64-8
• 化学式: C₁₉H₂₈N₂O₄
• 分子量: 348.442
• InChiKey: FJYYDYFDQJBQHU-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-benzyl 1-tert-butyl (S)-2-methyl-1,4-diazepane-1,4-dicarboxylate 在 10% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以96%的产率得到(2S)-六氢-2-甲基-1H-1,4-二氮杂卓-1-羧酸叔丁酯
  参考文献：
  名称：

  A Practical Synthesis of (S)-tert-Butyl 3-Methyl-1,4-diazepane-1-carboxylate, the Key Intermediate of Rho–Kinase Inhibitor K-115

  摘要：

  A practical synthesis of (S)-tert-butyl 3-methyl-1,4-diazepane-1-carboxylate has been established for supplying this key intermediate of Rho-kinase inhibitor K-115 in a multikilogram production. The chiral 1,4-diazepane was constructed by intramolecular Fukuyama-Mitsunobu cyclization of a N-nosyl diamino alcohol starting from the commercially available (S)- or (R)-2-aminopropan-1-ol. In the same manner, an enantiomeric pair of a structural isomer were prepared for demonstration of the synthetic utility.

  DOI：

  10.1055/s-0032-1316771
• 作为产物：
  描述：

  (S)-2-methyl-1-(2-nitrophenylsulfonyl)-1,4-diazepane 在 碳酸氢钠 、 potassium carbonate 、 苯硫酚 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙腈 为溶剂， 反应 6.5h， 生成 4-benzyl 1-tert-butyl (S)-2-methyl-1,4-diazepane-1,4-dicarboxylate
  参考文献：
  名称：

  A Practical Synthesis of (S)-tert-Butyl 3-Methyl-1,4-diazepane-1-carboxylate, the Key Intermediate of Rho–Kinase Inhibitor K-115

  摘要：

  A practical synthesis of (S)-tert-butyl 3-methyl-1,4-diazepane-1-carboxylate has been established for supplying this key intermediate of Rho-kinase inhibitor K-115 in a multikilogram production. The chiral 1,4-diazepane was constructed by intramolecular Fukuyama-Mitsunobu cyclization of a N-nosyl diamino alcohol starting from the commercially available (S)- or (R)-2-aminopropan-1-ol. In the same manner, an enantiomeric pair of a structural isomer were prepared for demonstration of the synthetic utility.

  DOI：

  10.1055/s-0032-1316771