2-氨基-2-苄基-3-羟基丙酸乙酯 | 78843-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氨基-2-苄基-3-羟基丙酸乙酯
• 英文名称: α-benzyl serine ethyl ester
• 英文别名: Ethyl alpha-(hydroxymethyl)phenylalaninate；ethyl 2-amino-2-benzyl-3-hydroxypropanoate
• CAS: 78843-74-0
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: NXXAORUDAHKZIP-UHFFFAOYSA-N

物化性质

• 沸点：
  376.2±37.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基-2-苄基-3-羟基丙酸乙酯 在 盐酸 、 lithium hydroxide 、 三甲基铝 、 碳酸氢钠 、 三乙胺 、 三苯基膦 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.5h， 生成 [3-((S)-2-Acetylamino-propionylamino)-3-benzyl-2-oxo-azetidin-1-yl]-methyl-carbamic acid benzyl ester
  参考文献：
  名称：

  A general strategy for the synthesis of azapeptidomimetic lactams

  摘要：

  A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.029
• 作为产物：
  描述：

  L-苯丙氨酸乙酯盐酸盐 在 盐酸 、 正丁基锂 、 magnesium sulfate 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 2-氨基-2-苄基-3-羟基丙酸乙酯
  参考文献：
  名称：

  A general strategy for the synthesis of azapeptidomimetic lactams

  摘要：

  A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.029

文献信息

• α-Hydroxymethylation of Schiff Bases Derived from α-Amino Acid Esters
  作者：Anna Calcagni、Domenico Rossi、Gino Lucente

  DOI：10.1055/s-1981-29476

  日期：——
• A general strategy for the synthesis of azapeptidomimetic lactams
  作者：Robert L. Broadrup、Bei Wang、William P. Malachowski

  DOI：10.1016/j.tet.2005.08.029

  日期：2005.10

  A selection of azapeptidomimetics containing constraining lactam rings have been prepared by Mitsunobu cyclization of serine/ homologated serine-azaalanine derivatives. These include sterically-congested beta-lactams, as well as gamma-butyrolactam and delta-valerolactam analogs. A novel azaamino acid acylation method was developed to prepare the sterically demanding alpha-benzyl-serine-azaalanine precursor. In all cases, the Mitsunobu conditions were highly efficient in forming the desired azapeptidomimetic lactams. The reported process represents a general strategy for the synthesis of peptidomimetic structures with a constraining lactam ring. (c) 2005 Elsevier Ltd. All rights reserved.