α-(N-tert-Butoxycarbonyl-N-benzylamino)acetophenone | 313657-36-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-(N-tert-Butoxycarbonyl-N-benzylamino)acetophenone
• 英文别名: tert-butyl benzyl(2-oxo-2-phenylethyl)carbamate；tert-butyl N-benzyl-N-phenacylcarbamate
• CAS: 313657-36-2
• 化学式: C₂₀H₂₃NO₃
• 分子量: 325.408
• InChiKey: ADBZASNEFHHWAT-UHFFFAOYSA-N

物化性质

• 沸点：
  461.0±34.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(N-tert-Butoxycarbonyl-N-benzylamino)acetophenone 在 sodium tetrahydroborate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 生成 2-(benzyl(tert-butoxycarbonyl)amino)-1-phenylethyl 4-nitrobenzenesulfonate
  参考文献：
  名称：

  Synthesis and 2D QSAR of O-sulphonated β-aminols derivatives as novel antifungal and antibacterial agents

  摘要：

  Synthesis of a series of beta-aminol derivatives using regioselective opening reaction catalyzed by SiO2 (60-120 mesh) and O-sulphonation in THF-KOH system, comprising tert-butoxycarbonyl at secondary nitrogen and evaluate for various stains of bacteria and fungi. SAR study of synthesized compound using backward regression analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.078
• 作为产物：
  描述：

  2-溴苯乙酮 在 三乙胺 作用下， 生成 α-(N-tert-Butoxycarbonyl-N-benzylamino)acetophenone
  参考文献：
  名称：

  Synthesis and 2D QSAR of O-sulphonated β-aminols derivatives as novel antifungal and antibacterial agents

  摘要：

  Synthesis of a series of beta-aminol derivatives using regioselective opening reaction catalyzed by SiO2 (60-120 mesh) and O-sulphonation in THF-KOH system, comprising tert-butoxycarbonyl at secondary nitrogen and evaluate for various stains of bacteria and fungi. SAR study of synthesized compound using backward regression analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.078

文献信息

• Weinreb amide based synthetic equivalents for convenient access to 4-aryl-1,2,3,4-tetrahydroisoquinolines
  作者：Harikrishna Kommidi、Sivaraman Balasubramaniam、Indrapal Singh Aidhen

  DOI：10.1016/j.tet.2010.03.074

  日期：2010.5

  N-methoxy-N-methyl-N′-benzyl-N′-tert-butyloxy carbonyl glycinamide based on WA functionality were developed for the convenient synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline framework. Two simple reactions, N-benzylation and addition of arylmagnesium halide on the WA functionality of the former afforded the key intermediate for convenient synthesis of N-phenylsulfonyl protected 4-aryl-1,2,3,4-tetrahydroisoquinoline

  新的合成的等同物，Ñ甲氧基Ñ甲基Ñ ' -苯磺酰基甘氨酰胺和Ñ甲氧基Ñ甲基Ñ ' -苄基- ñ ' -叔-butyloxy羰基于WA功能甘氨酰胺被用于的方便合成开发4-芳基-1,2,3,4-四氢异喹啉骨架。两个简单的反应，N-苄基化和芳基卤化镁在前者的WA功能上的加成提供了方便合成N的关键中间体-苯磺酰基通过还原和酸促进的环化作用来保护4-芳基-1,2,3,4-四氢异喹啉。对于后者，在WA官能团上添加卤化芳基镁，然后按照相同的方案，以良好的产率直接合成了4-芳基-1,2,3,4-四氢异喹啉。酸促进的环化步骤能够同时去除N -Boc保护。
• Enantioselective synthesis of β-hydroxy amines and aziridines using asymmetric transfer hydrogenation of α-amino ketones
  作者：Aparecida M. Kawamoto、Martin Wills

  DOI：10.1039/b102895m

  日期：——

  Enantioselective transfer hydrogenation of α-amino ketones is an effective method for the asymmetric synthesis of β-hydroxy amines and aziridines.

  α-氨基酮的对映选择性转移氢化是一种有效的方法，用于手性合成β-羟基胺和氮丙啶。
• Enantioselective synthesis of β-hydroxy amines and aziridines using asymmetric transfer hydrogenation of α-amido ketones
  作者：Aparecida Kawamoto、Martin Wills

  DOI：10.1016/s0957-4166(00)00310-4

  日期：2000.8

  A rapid, expedient and enantioselective method for the synthesis of β-hydroxy amines and monosubstituted aziridines in up to 99% e.e., via asymmetric transfer hydrogenation of α-amido ketones, is described.

  描述了一种通过α-酰胺基酮的不对称转移加氢合成高达99％ee的β-羟胺和单取代氮丙啶的快速，便捷和对映选择性的方法。
• Synthesis and 2D QSAR of O-sulphonated β-aminols derivatives as novel antifungal and antibacterial agents
  作者：Sugandha Sharma、Atindra K. Pandey、Praveen K. Shukla、Anil K. Saxena

  DOI：10.1016/j.bmcl.2011.08.078

  日期：2011.11

  Synthesis of a series of beta-aminol derivatives using regioselective opening reaction catalyzed by SiO2 (60-120 mesh) and O-sulphonation in THF-KOH system, comprising tert-butoxycarbonyl at secondary nitrogen and evaluate for various stains of bacteria and fungi. SAR study of synthesized compound using backward regression analysis. (C) 2011 Elsevier Ltd. All rights reserved.