N-[2-(butylamino)-2-oxo-1-phenylethyl]-N-(2-hydroxyethyl)-2-(methanesulfonamido)benzamide | 934421-03-1

• 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: N-[2-(butylamino)-2-oxo-1-phenylethyl]-N-(2-hydroxyethyl)-2-(methanesulfonamido)benzamide
• CAS: 934421-03-1
• 化学式: C₂₂H₂₉N₃O₅S
• 分子量: 447.555
• InChiKey: YVKRACWSOPDIBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[2-(butylamino)-2-oxo-1-phenylethyl]-N-(2-hydroxyethyl)-2-(methanesulfonamido)benzamide 在 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到N-butyl-2-(1-methylsulfonyl-5-oxo-2,3-dihydro-1,4-benzodiazepin-4-yl)-2-phenylacetamide
  参考文献：
  名称：

  Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution:  Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-ones and of Their Benzo-Fused Derivatives

  摘要：

  A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.

  DOI：

  10.1021/jo062626z
• 作为产物：
  描述：

  苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 3 A molecular sieve 、 4 A molecular sieve 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 25.0h， 生成 N-[2-(butylamino)-2-oxo-1-phenylethyl]-N-(2-hydroxyethyl)-2-(methanesulfonamido)benzamide
  参考文献：
  名称：

  Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution:  Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-ones and of Their Benzo-Fused Derivatives

  摘要：

  A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.

  DOI：

  10.1021/jo062626z

文献信息

• Ugi Multicomponent Reaction Followed by an Intramolecular Nucleophilic Substitution:  Convergent Multicomponent Synthesis of 1-Sulfonyl 1,4-Diazepan-5-ones and of Their Benzo-Fused Derivatives
  作者：Luca Banfi、Andrea Basso、Giuseppe Guanti、Nicola Kielland、Claudio Repetto、Renata Riva

  DOI：10.1021/jo062626z

  日期：2007.3.1

  A short, two-step approach to the synthesis of diazepane or diazocane systems, based on a Ugi multicomponent reaction followed by a subsequent intramolecular S(N)2 reaction was studied. 1-Sulfonyl tetrahydrobenzo[e]-1,4-diazepin-1-ones 1 were obtained in very high yield through a Ugi multicomponent reaction followed by Mitsunobu cyclization. On the other hand, aliphatic 1-sulfonyl 1,4-diazepan-5-ones 2 could be obtained employing different cyclization conditions (sulfuryl diimidazole). A similar approach toward diazocane rings using hydroxamates as nucleophiles was less successful, affording only O-cyclized adducts or unexpected side products. A mechanistic explanation of the observed outcomes is proposed.