N-(benzyloxycarbonyl)-β-(diethylamino)-L-alanine | 160885-21-2

• 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: N-(benzyloxycarbonyl)-β-(diethylamino)-L-alanine
• 英文别名: 3-(Diethylamino)-N-[(phenylmethoxy)carbonyl]-L-alanine；(2S)-3-(diethylamino)-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 160885-21-2
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: PYWYETUZSQHFCK-ZDUSSCGKSA-N

物化性质

• 沸点：
  466.1±45.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苄氧羰基-L-丝氨酸(Β-内酯) 、 三甲基硅烷基二乙胺 以 乙腈 为溶剂， 反应 9.0h， 以78%的产率得到N-(benzyloxycarbonyl)-β-(diethylamino)-L-alanine
  参考文献：
  名称：

  三甲基甲硅烷基胺与N-Cbz-L-丝氨酸-β-内酯的反应：光学上纯净的β-氨基-L-丙氨酸衍生物的便捷途径

  摘要：

  三甲基甲硅烷基胺Me 3 Si-NR 2主要通过内酯环的烷基氧裂解与乙腈中的N-Cbz-L-丝氨酸-β-内酯反应，得到光学纯的N-Cbz-β-氨基-L-丙氨酸衍生物良品率高。使用卤化溶剂（例如氯仿）会改变区域特异性，从而主要产生酰基氧裂解并生成N-Cbz-L-丝氨酸酰胺。后者也通过铝胺试剂与β-内酯的反应而获得。

  DOI：

  10.1016/s0040-4039(00)78354-7

文献信息

• One-pot synthesis of N-Cbz-l-BMAA and derivatives from N-Cbz-l-serine
  作者：Sidnei Moura、Ernani Pinto

  DOI：10.1016/j.tetlet.2007.01.149

  日期：2007.3

  We report herein an asymmetric synthesis of the modified amino acid N-CbZ-L-BMAA and seven of its alkyl derivatives (2a-h) from N-CbZ-L-serine via ring-opening of the P-lactone (formed under modified Mitsunobu conditions) by different amines. This procedure is simple, one-pot and can generate various derivatives that can be investigated for their toxicological effects. In addition, it can be employed to produce analytical standards for water monitoring as well as labeled compounds for biotransformation studies. This toxin has been the focus of serious ecological and public concern since its implication in degenerative disease such as Alzheimer and Parkinsonism dementia. (c) 2007 Elsevier Ltd. All rights reserved.
• Reaction of trimethylsilylamines with N-Cbz-L-serine-β-lactone: A convenient route to optically pure β-amino-L-alanine derivatives
  作者：Elaref S. Ratemi、John C. Vederas

  DOI：10.1016/s0040-4039(00)78354-7

  日期：1994.10

  Trimethylsilylamines, Me3Si-NR2, react with N-Cbz-L-serine-β-lactone in acetonitrile primarily by alkyl oxygen cleavage of the lactone ring to give optically pure N-Cbz-β-amino-L-alanine derivatives in good yields. Use of halogenated solvents such as chloroform alters the regiospecificity to give primarily acyl oxygen cleavage and generate amides of N-Cbz-L-serine. The latter are also obtained by reaction

  三甲基甲硅烷基胺Me 3 Si-NR 2主要通过内酯环的烷基氧裂解与乙腈中的N-Cbz-L-丝氨酸-β-内酯反应，得到光学纯的N-Cbz-β-氨基-L-丙氨酸衍生物良品率高。使用卤化溶剂（例如氯仿）会改变区域特异性，从而主要产生酰基氧裂解并生成N-Cbz-L-丝氨酸酰胺。后者也通过铝胺试剂与β-内酯的反应而获得。