3,4,5,6-tetrahydro-(4S,5S)-2-benzyl-7-[(2-bromo)benzyl]-4,5-O-isopropylidene-1,2,7-thiadiazepine 1,1-dioxide | 862884-26-2

• 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: 3,4,5,6-tetrahydro-(4S,5S)-2-benzyl-7-[(2-bromo)benzyl]-4,5-O-isopropylidene-1,2,7-thiadiazepine 1,1-dioxide
• 英文别名: (4S,5S)-3,4,5,6-tetrahydro-2-(2-bromobenzyl)-7-benzyl-4,5-O-isopropylidene-1,2,7-thiadiazepine 1,1-dioxide；(3aS,8aS)-7-benzyl-5-[(2-bromophenyl)methyl]-2,2-dimethyl-3a,4,8,8a-tetrahydro-[1,3]dioxolo[4,5-d][1,2,7]thiadiazepine 6,6-dioxide
• CAS: 862884-26-2
• 化学式: C₂₁H₂₅BrN₂O₄S
• 分子量: 481.41
• InChiKey: MMQIHQBHMOAHIO-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,5,6-tetrahydro-(4S,5S)-2-benzyl-7-[(2-bromo)benzyl]-4,5-O-isopropylidene-1,2,7-thiadiazepine 1,1-dioxide 在 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 1.75h， 生成 (4S,5S)-3,4,5,6-tetrahydro-2-(N-benzyl-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)-O-isopropylidene-1,2,7-thiadiazepine 1,1-dioxide 在 potassium carbonate 、 silver(l) oxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3,4,5,6-tetrahydro-(4S,5S)-2-benzyl-7-[(2-bromo)benzyl]-4,5-O-isopropylidene-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

文献信息

• Synthesis of a small library of non-symmetric cyclic sulfamide HIV-1 protease inhibitors
  作者：Anna Ax、Advait A. Joshi、Kristina M. Orrling、Lotta Vrang、Bertil Samuelsson、Anders Hallberg、Anders Karlén、Mats Larhed

  DOI：10.1016/j.tet.2010.04.023

  日期：2010.6

  A set of 11 non-symmetric cyclic sulfamide HIV-1 protease inhibitors were synthesized and evaluated. The use of a key microwave-assisted silver(I) oxide mediated selective mono N-benzylation reaction enabled fast and straightforward synthesis. The Ki values of the new inhibitors ranged between 0.28 μM and >20 μM.

  合成并评估了一组11种非对称环硫酰胺HIV-1蛋白酶抑制剂。使用关键的微波辅助氧化银（I）介导的选择性单N-苄基化反应可实现快速直接的合成。新抑制剂的K i值介于0.28μM和> 20μM之间。
• Microwave Irradiation as a High-Speed Tool for Activation of Sluggish Aryl Chlorides in Grignard Reactions
  作者：Peter Nilsson、Henrik Gold、Mats Larhed

  DOI：10.1055/s-2005-869856

  日期：——

  Microwave Irradiation as a High-Speed Toll for Activation of Sluggish Aryl Chlorides in Grignard Reactions

  微波辐射作为格氏反应中缓慢活化芳基氯化物的高速收费
• 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.