(3-Benzyl-2-oxo-oxetan-3-yl)-carbamic acid tert-butyl ester | 833484-36-9

• 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: (3-Benzyl-2-oxo-oxetan-3-yl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-(3-benzyl-2-oxooxetan-3-yl)carbamate
• CAS: 833484-36-9
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: BIIRBXBJTQMJHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  139-140 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  425.9±34.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-Benzyl-2-oxo-oxetan-3-yl)-carbamic acid tert-butyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 三甲基铝 、 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 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 (S)-2-Acetylamino-N-(3-benzyl-1-methylamino-2-oxo-azetidin-3-yl)-propionamide
  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 、 lithium hydroxide 、 正丁基锂 、 碳酸氢钠 、 magnesium sulfate 、 三乙胺 、 二异丙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 8.5h， 生成 (3-Benzyl-2-oxo-oxetan-3-yl)-carbamic acid tert-butyl 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

文献信息

• A convenient transformation of α-alkylserines into α-halogenomethyl-α-alkylglycines
  作者：Adam Kudaj、Aleksandra Olma

  DOI：10.1016/j.tetlet.2008.08.098

  日期：2008.11

  An efficient and facile synthesis of N-Boc-alpha-chloromethyl- and alpha-bromomethyl-alpha-alkylglycines is reported that involves cyclization of N-Boc-alpha-alkylserines to the corresponding beta-lactones under Mitsunobu reaction conditions, followed by ring opening with anhydrous MgCl2 or MgBr2. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.