benzyl (S)-3-methyl-4-[(2-nitrophenyl)sulfonyl]-1,4-diazepane-1-carboxylate | 1411975-62-6

• 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: benzyl (S)-3-methyl-4-[(2-nitrophenyl)sulfonyl]-1,4-diazepane-1-carboxylate
• 英文别名: benzyl (3S)-3-methyl-4-(2-nitrophenyl)sulfonyl-1,4-diazepane-1-carboxylate
• CAS: 1411975-62-6
• 化学式: C₂₀H₂₃N₃O₆S
• 分子量: 433.485
• InChiKey: WTPIGVXIDLJYBC-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (S)-3-methyl-4-[(2-nitrophenyl)sulfonyl]-1,4-diazepane-1-carboxylate 在 10% Pd/C 、 氢气 、 potassium carbonate 、 苯硫酚 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 21.5h， 生成 (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 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 以97%的产率得到benzyl (S)-3-methyl-4-[(2-nitrophenyl)sulfonyl]-1,4-diazepane-1-carboxylate
  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

文献信息

• A Practical Synthesis of (S)-tert-Butyl 3-Methyl-1,4-diazepane-1-carboxylate, the Key Intermediate of Rho–Kinase Inhibitor K-115
  作者：Kimiyuki Shibuya、Noriaki Gomi、Akiyasu Kouketsu、Tadaaki Ohgiya

  DOI：10.1055/s-0032-1316771

  日期：——

  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.