ethyl 2-(N-benzyl-2-bromobutanamido)acetate | 872165-00-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(N-benzyl-2-bromobutanamido)acetate
• 英文别名: Ethyl 2-[benzyl(2-bromobutanoyl)amino]acetate
• CAS: 872165-00-9
• 化学式: C₁₅H₂₀BrNO₃
• 分子量: 342.233
• InChiKey: TXBPDICNYGRWLG-UHFFFAOYSA-N

物化性质

• 沸点：
  429.0±40.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  ethyl 2-(N-benzyl-2-bromobutanamido)acetate 在 tetraethylammonium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 (2S,3S)-1-Benzyl-3-ethyl-4-oxo-azetidine-2-carboxylic acid ethyl ester 、 trans-1-benzyl-4-ethoxycarbonyl-3-ethyl-2-azetidinone
  参考文献：
  名称：

  Electrogenerated cyanomethyl anion in organic synthesis: a simple diastereoselective synthesis of cis-3-alkyl-1-benzyl-4-ethoxycarbonyl-β-lactams

  摘要：

  A ready diastereoselective synthesis of cis-3-alkyl-l-benzyl-4-ethoxycarbonyl-beta-lactams has been developed by galvanostatic electrolysis of MeCN-Et4NPF6 Solutions and subsequent addition of a N-(ethoxycarbonyl)methyl-N-benzyl-2-bromoalkyl-carboxamide. The yields in beta-lactams are very high and the cis isomers have been obtained in a large excess, the cis/trans ratios varying from 87/13 to 93/07. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.008
• 作为产物：
  描述：

  2-溴丁酰溴 、 N-苄基甘氨酸乙酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 ethyl 2-(N-benzyl-2-bromobutanamido)acetate
  参考文献：
  名称：

  Electrogenerated cyanomethyl anion in organic synthesis: a simple diastereoselective synthesis of cis-3-alkyl-1-benzyl-4-ethoxycarbonyl-β-lactams

  摘要：

  A ready diastereoselective synthesis of cis-3-alkyl-l-benzyl-4-ethoxycarbonyl-beta-lactams has been developed by galvanostatic electrolysis of MeCN-Et4NPF6 Solutions and subsequent addition of a N-(ethoxycarbonyl)methyl-N-benzyl-2-bromoalkyl-carboxamide. The yields in beta-lactams are very high and the cis isomers have been obtained in a large excess, the cis/trans ratios varying from 87/13 to 93/07. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.008

文献信息

• Electrogenerated cyanomethyl anion in organic synthesis: a simple diastereoselective synthesis of cis-3-alkyl-1-benzyl-4-ethoxycarbonyl-β-lactams
  作者：Marta Feroci、Jean Lessard、Monica Orsini、Achille Inesi

  DOI：10.1016/j.tetlet.2005.10.008

  日期：2005.12

  A ready diastereoselective synthesis of cis-3-alkyl-l-benzyl-4-ethoxycarbonyl-beta-lactams has been developed by galvanostatic electrolysis of MeCN-Et4NPF6 Solutions and subsequent addition of a N-(ethoxycarbonyl)methyl-N-benzyl-2-bromoalkyl-carboxamide. The yields in beta-lactams are very high and the cis isomers have been obtained in a large excess, the cis/trans ratios varying from 87/13 to 93/07. (c) 2005 Elsevier Ltd. All rights reserved.