2-((3aS,8aS)-7-Benzyl-2,2-dimethyl-6,6-dioxo-hexahydro-1,3-dioxa-6λ⁶-thia-5,7-diaza-azulen-5-ylmethyl)-N-phenyl-benzamide | 891144-23-3

• 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: 2-((3aS,8aS)-7-Benzyl-2,2-dimethyl-6,6-dioxo-hexahydro-1,3-dioxa-6λ⁶-thia-5,7-diaza-azulen-5-ylmethyl)-N-phenyl-benzamide
• 英文别名: 2-[[(3aS,8aS)-7-benzyl-2,2-dimethyl-6,6-dioxo-3a,4,8,8a-tetrahydro-[1,3]dioxolo[4,5-d][1,2,7]thiadiazepin-5-yl]methyl]-N-phenylbenzamide
• CAS: 891144-23-3
• 化学式: C₂₈H₃₁N₃O₅S
• 分子量: 521.637
• InChiKey: OZRABQDOXGUMJB-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  96.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-((3aS,8aS)-7-Benzyl-2,2-dimethyl-6,6-dioxo-hexahydro-1,3-dioxa-6λ⁶-thia-5,7-diaza-azulen-5-ylmethyl)-N-phenyl-benzamide 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.75h， 生成 (4S,5S)-3,4,5,6-tetrahydro-2-(N-phenyl-2-amido-benzyl)-7-benzyl-4,5-dihydroxy-1,2,7-thiadiazepine 1,1-dioxide
  参考文献：
  名称：

  Fast and selective synthesis of novel cyclic sulfamide HIV-1 protease inhibitors under controlled microwave heating

  摘要：

  A novel and highly selective silver-promoted monobenzylation method was developed to promote synthesis of nonsymmetrical sulfamide-based HIV-1 inhibitors. Microwave-accelerated palladium-catalyzed N-amide arylation- and aminocarbonylation reactions were employed for rapid and reliable compound generation. With this class of inhibitory agents, six active inhibitors were identified, the most potent inhibitor possessing a K-i-value of 20 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.094
• 作为产物：
  描述：

  (4S,5S)-3,4,5,6-tetrahydro-2-(2-bromobenzyl)-4,5-O-isopropylidene-1,2,7-thiadiazepine 1,1-dioxide 在 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-((3aS,8aS)-7-Benzyl-2,2-dimethyl-6,6-dioxo-hexahydro-1,3-dioxa-6λ⁶-thia-5,7-diaza-azulen-5-ylmethyl)-N-phenyl-benzamide
  参考文献：
  名称：

  Fast and selective synthesis of novel cyclic sulfamide HIV-1 protease inhibitors under controlled microwave heating

  摘要：

  A novel and highly selective silver-promoted monobenzylation method was developed to promote synthesis of nonsymmetrical sulfamide-based HIV-1 inhibitors. Microwave-accelerated palladium-catalyzed N-amide arylation- and aminocarbonylation reactions were employed for rapid and reliable compound generation. With this class of inhibitory agents, six active inhibitors were identified, the most potent inhibitor possessing a K-i-value of 20 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.11.094

文献信息

• Fast and selective synthesis of novel cyclic sulfamide HIV-1 protease inhibitors under controlled microwave heating
  作者：Henrik Gold、Anna Ax、Lotta Vrang、Bertil Samuelsson、Anders Karlén、Anders Hallberg、Mats Larhed

  DOI：10.1016/j.tet.2005.11.094

  日期：2006.5

  A novel and highly selective silver-promoted monobenzylation method was developed to promote synthesis of nonsymmetrical sulfamide-based HIV-1 inhibitors. Microwave-accelerated palladium-catalyzed N-amide arylation- and aminocarbonylation reactions were employed for rapid and reliable compound generation. With this class of inhibitory agents, six active inhibitors were identified, the most potent inhibitor possessing a K-i-value of 20 nM. (c) 2006 Elsevier Ltd. All rights reserved.