methyl N-[1-(butylamino)-1,3-dioxo-3-phenylpropan-2-yl]-N-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]methyl]carbamate | 1244783-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl N-[1-(butylamino)-1,3-dioxo-3-phenylpropan-2-yl]-N-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]methyl]carbamate
• CAS: 1244783-52-5
• 化学式: C₂₇H₃₅N₃O₆
• 分子量: 497.591
• InChiKey: SPDAOROTQGGVMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl N-[1-(butylamino)-1,3-dioxo-3-phenylpropan-2-yl]-N-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]methyl]carbamate 在 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 生成 C₂₂H₂₅N₃O₃
  参考文献：
  名称：

  Concise preparation of novel tricyclic chemotypes: fused hydantoin–benzodiazepines

  摘要：

  The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance are high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO(2)-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.131
• 作为产物：
  描述：

  carbonic acid monomethyl ester 、 异腈基正丁烷 、 苯基丙醇水合物 、 N-[2-(氨基甲基)苯基]氨基甲酸叔丁酯 在 二氧化碳 作用下， 反应 16.0h， 以39%的产率得到methyl N-[1-(butylamino)-1,3-dioxo-3-phenylpropan-2-yl]-N-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]methyl]carbamate
  参考文献：
  名称：

  Concise preparation of novel tricyclic chemotypes: fused hydantoin–benzodiazepines

  摘要：

  The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance are high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO(2)-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.131

文献信息

• Concise preparation of novel tricyclic chemotypes: fused hydantoin–benzodiazepines
  作者：Steven Gunawan、Gary S. Nichol、Shashi Chappeta、Justin Dietrich、Christopher Hulme

  DOI：10.1016/j.tetlet.2010.06.131

  日期：2010.9

  The following article describes a concise synthesis of a collection of 4,5-dihydro-1H-benzo[e][1,4]diazepines fused to a hydantoin ring. Molecular complexity and biological relevance are high and structures are generated in a mere three steps, employing the Ugi reaction to assemble diversity reagents. The protocol represents a novel UDC (Ugi-deprotect-cyclize) strategy employed in the Ugi-5-component CO(2)-mediated condensation, followed by further cyclization under basic conditions, to afford the fused hydantoin. Mechanistic caveats, dependent on the aldehydes of choice will be revealed and a facile oxidation of the final products to imidazolidenetriones is briefly discussed. (C) 2010 Elsevier Ltd. All rights reserved.