2-(2,5-dioxopyrrolidin-1-ylmethyl)acrylic acid tert-butyl ester | 858125-67-4

• 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: 2-(2,5-dioxopyrrolidin-1-ylmethyl)acrylic acid tert-butyl ester
• 英文别名: Tert-butyl 2-[(2,5-dioxopyrrolidin-1-yl)methyl]prop-2-enoate；tert-butyl 2-[(2,5-dioxopyrrolidin-1-yl)methyl]prop-2-enoate
• CAS: 858125-67-4
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: PXLYUYDJCFHKFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,5-dioxopyrrolidin-1-ylmethyl)acrylic acid tert-butyl ester 、 碘代环戊烷 在 magnesium iodide 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到
  参考文献：
  名称：

  Enantioselective radical reactions. Evaluation of nitrogen protecting groups in the synthesis of β2-amino acids

  摘要：

  We have investigated the effect of nitrogen protecting groups in radical addition trapping experiments leading to beta(2)-amino acids. Of the three N-protecting groups examined, the phthalimido group was optimal with respect to both yields and enantioselectivity. Additionally, radical additions to more complex acrylates were also investigated, which provided access to functionalized beta(2)-amino acids in modest selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.01.018
• 作为产物：
  描述：

  丁二酰亚胺 、 tert-butyl 2-hydroxymethylacrylate 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2,5-dioxopyrrolidin-1-ylmethyl)acrylic acid tert-butyl ester
  参考文献：
  名称：

  对映选择性烯醇铑质子化。合成β2-氨基酸的新方法。

  摘要：

  [反应：见正文]芳基硼酸向α-甲基氨基丙烯酸酯的铑催化共轭加成，然后氧杂-π-烯丙基铑中间体的对映选择性质子化，提供了被芳基取代的β（2）-氨基酸的途径。已经评估了反应的不同变量对对映选择性水平的影响。

  DOI：

  10.1021/ol050630b

文献信息

• Enantioselective Rhodium Enolate Protonations. A New Methodology for the Synthesis of β²-Amino Acids
  作者：Mukund P. Sibi、Hiroto Tatamidani、Kalyani Patil

  DOI：10.1021/ol050630b

  日期：2005.6.1

  [reaction: see text] Rhodium-catalyzed conjugate addition of an aryl boronic acid to alpha-methylamino acrylates followed by enantioselective protonation of the oxa-pi-allylrhodium intermediate provides access to aryl-substituted beta(2)-amino acids. The impact of the different variables of the reaction on the levels of enantioselectivity has been assessed.

  [反应：见正文]芳基硼酸向α-甲基氨基丙烯酸酯的铑催化共轭加成，然后氧杂-π-烯丙基铑中间体的对映选择性质子化，提供了被芳基取代的β（2）-氨基酸的途径。已经评估了反应的不同变量对对映选择性水平的影响。
• Enantioselective radical reactions. Evaluation of nitrogen protecting groups in the synthesis of β2-amino acids
  作者：Mukund P. Sibi、Kalyani Patil

  DOI：10.1016/j.tetasy.2006.01.018

  日期：2006.2

  We have investigated the effect of nitrogen protecting groups in radical addition trapping experiments leading to beta(2)-amino acids. Of the three N-protecting groups examined, the phthalimido group was optimal with respect to both yields and enantioselectivity. Additionally, radical additions to more complex acrylates were also investigated, which provided access to functionalized beta(2)-amino acids in modest selectivity. (c) 2006 Elsevier Ltd. All rights reserved.