N-[1-cyclohexyl-2-oxo-2-(2,4,4-trimethylpentan-2-ylamino)ethyl]-N-(2-hydroxyethyl)-2-[(4-methylphenyl)sulfonylamino]benzamide | 934420-98-1

• 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-[1-cyclohexyl-2-oxo-2-(2,4,4-trimethylpentan-2-ylamino)ethyl]-N-(2-hydroxyethyl)-2-[(4-methylphenyl)sulfonylamino]benzamide
• CAS: 934420-98-1
• 化学式: C₃₂H₄₇N₃O₅S
• 分子量: 585.808
• InChiKey: AZCYCYDRGHYOFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 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-[1-cyclohexyl-2-oxo-2-(2,4,4-trimethylpentan-2-ylamino)ethyl]-N-(2-hydroxyethyl)-2-[(4-methylphenyl)sulfonylamino]benzamide 在 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到2-cyclohexyl-2-[1-(4-methylphenyl)sulfonyl-5-oxo-2,3-dihydro-1,4-benzodiazepin-4-yl]-N-(2,4,4-trimethylpentan-2-yl)acetamide
  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：

  环己烷基甲醛 、 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-[1-cyclohexyl-2-oxo-2-(2,4,4-trimethylpentan-2-ylamino)ethyl]-N-(2-hydroxyethyl)-2-[(4-methylphenyl)sulfonylamino]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.