1,3-di[N-(N-tert-butyloxycarbonyl)benzylamino]acetone | 253590-74-8

• 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: 1,3-di[N-(N-tert-butyloxycarbonyl)benzylamino]acetone
• 英文别名: tert-butyl N-benzyl-N-[3-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-2-oxopropyl]carbamate
• CAS: 253590-74-8
• 化学式: C₂₇H₃₆N₂O₅
• 分子量: 468.593
• InChiKey: SQEXJNDYXHBORL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-di[N-(N-tert-butyloxycarbonyl)benzylamino]acetone 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 Benzyl-{2-[benzyl-({benzyl-[3-(benzyl-tert-butoxycarbonyl-amino)-propanoyl]-amino}-oxo-propyl)-carbamoyl]-ethyl}-carbamic acid dimethyl-ethyl ester
  参考文献：
  名称：

  New anti-HIV derivatives: synthesis and antiviral evaluation

  摘要：

  A small focused library of 18 compounds incorporating the motif 1,3-(N,N'-dibenzyl)diamino-2-propanol has been synthesized, using adapted synthetic methodologies. These series of compounds were evaluated for their in vitro anti-HIV activity on infected MT(4) cells (syncytium formation observation). Some of the new synthesized compounds show potent anti-HIV activities. EC(50) values for compounds (31, 40, 34, 37 and 46) range From 0.1 to 1 mu M. In order to determine at which level these new derivatives interfere with the HIV replicative cycle, inhibition assays on recombinant HIV protease and HIV integrase have been performed. None of the compounds were found active on these two enzymatic targets. Experiments are in progress in order to identify their biological target within the HIV replicative cycle. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00055-9
• 作为产物：
  描述：

  1,3-di-[N-benzyl-N-[(tert-butyloxy)carbonyl]amino]-2-hydroxypropane 在 2,2,6,6-tetramethyl-piperidine-N-oxyl sodium hypochlorite 、 碳酸氢钠 、 potassium bromide 作用下， 以 二氯甲烷 、 水 为溶剂， 以93%的产率得到1,3-di[N-(N-tert-butyloxycarbonyl)benzylamino]acetone
  参考文献：
  名称：

  α-硫代苯氧基-羟乙基酰胺衍生物的合成及其抗HIV活性。

  摘要：

  以S-苯基苯硫代磺酸盐为硫代磺酰化剂，合成了一系列含有新型α-硫代苯氧基羟乙基酰胺核的新型抗HIV衍生物。一些新合成的化合物（1a，1c，1g，1i，1j和1l）在有效浓度（EC（50））为0.1-1 microM的细胞培养试验（合胞体形成）中抑制了HIV复制。在各种拟模拟肽主链内并入噻吩氧基取代提供了一系列高效的HIV抑制剂。

  DOI：

  10.1016/s0223-5234(00)80031-8

文献信息

• Synthesis and anti-HIV activity of α-thiophenoxy-hydroxyethylamide derivatives
  作者：Martial Medou、Ghislaine Priem、Luc Rocheblave、Gérard Pepe、Monique Meyer、Jean-Claude Chermann、Jean-Louis Kraus

  DOI：10.1016/s0223-5234(00)80031-8

  日期：1999.7

  A series of new anti-HIV derivatives containing a novel alpha-thiophenoxyhydroxyethylamide core have been synthesized, using S-phenylbenzenethiosulfonate as the thiosulfenylating reagent. Some of the new synthesized compounds (1a, 1c, 1g, 1i, 1j and 1l) inhibited HIV replication in cell culture assays (syncytia formation) with effective concentrations (EC(50)) ranging from 0.1-1 microM. Incorporation

  以S-苯基苯硫代磺酸盐为硫代磺酰化剂，合成了一系列含有新型α-硫代苯氧基羟乙基酰胺核的新型抗HIV衍生物。一些新合成的化合物（1a，1c，1g，1i，1j和1l）在有效浓度（EC（50））为0.1-1 microM的细胞培养试验（合胞体形成）中抑制了HIV复制。在各种拟模拟肽主链内并入噻吩氧基取代提供了一系列高效的HIV抑制剂。
• Seebach’s Conjunctive Reagent Enables Double Cyclizations
  作者：Brent D. Chandler、Jason T. Roland、Yukai Li、Erik J. Sorensen

  DOI：10.1021/ol100845z

  日期：2010.6.18

  When ketones flanked on both sides by nucleophilic atoms react with Seebach's nitropropenyl pivaloate reagent, direct couplings take place to give two new ring systems and three bonds. Cis-ring fusions are observed in unions leading to 5,5-, 5,6-, and 6,6-bicycles. Densely functionalized and rigid frameworks may be rapidly formed by the chemistry described herein.
• New anti-HIV derivatives: synthesis and antiviral evaluation
  作者：C. De Michelis、L. Rocheblave、G. Priem、J.C. Chermann、J.L. Kraus

  DOI：10.1016/s0968-0896(00)00055-9

  日期：2000.6

  A small focused library of 18 compounds incorporating the motif 1,3-(N,N'-dibenzyl)diamino-2-propanol has been synthesized, using adapted synthetic methodologies. These series of compounds were evaluated for their in vitro anti-HIV activity on infected MT(4) cells (syncytium formation observation). Some of the new synthesized compounds show potent anti-HIV activities. EC(50) values for compounds (31, 40, 34, 37 and 46) range From 0.1 to 1 mu M. In order to determine at which level these new derivatives interfere with the HIV replicative cycle, inhibition assays on recombinant HIV protease and HIV integrase have been performed. None of the compounds were found active on these two enzymatic targets. Experiments are in progress in order to identify their biological target within the HIV replicative cycle. (C) 2000 Elsevier Science Ltd. All rights reserved.