2-[3-[(2-Methylpropan-2-yl)oxycarbonyl]-1,3-oxazinan-2-yl]acetic acid | 313694-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-[3-[(2-Methylpropan-2-yl)oxycarbonyl]-1,3-oxazinan-2-yl]acetic acid
• CAS: 313694-81-4
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: GFBJYXMUIJXPSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(3-羟丙基)氨基甲酸叔丁酯 、 丙烯酸 在 双(乙腈)氯化钯(II) 作用下， 以 乙二醇二甲醚 为溶剂， 反应 6.0h， 以32%的产率得到2-[3-[(2-Methylpropan-2-yl)oxycarbonyl]-1,3-oxazinan-2-yl]acetic acid
  参考文献：
  名称：

  2,2-Difunctionalization of Alkenes via Pd(II)-Catalyzed Aza-Wacker Reactions

  摘要：

  N-Ts and N-Boc derivatives of 1,2-diamines and 1,2-amino alcohols are shown to undergo efficient Pd(II)-catalyzed aza-Wacker reactions with a large range of electron-deficient alkenes. The resulting enamine intermediate generally undergoes cyclization with the second heteroatom to form 1,3-heterocycles. The sequence facilitates the rapid synthesis of saturated oxazolidines, imidazolidines, and their derivatives. Use of N-L-valinol derivatives results in highly diastereoselective reactions, where the net stereochemical outcome diverges between N-Ts and N-Boc.

  DOI：

  10.1021/ol102956x

文献信息

• 2,2-Difunctionalization of Alkenes via Pd(II)-Catalyzed Aza-Wacker Reactions
  作者：Luke D. Elliott、Joe W. Wrigglesworth、Brian Cox、Guy C. Lloyd-Jones、Kevin I. Booker-Milburn

  DOI：10.1021/ol102956x

  日期：2011.2.18

  N-Ts and N-Boc derivatives of 1,2-diamines and 1,2-amino alcohols are shown to undergo efficient Pd(II)-catalyzed aza-Wacker reactions with a large range of electron-deficient alkenes. The resulting enamine intermediate generally undergoes cyclization with the second heteroatom to form 1,3-heterocycles. The sequence facilitates the rapid synthesis of saturated oxazolidines, imidazolidines, and their derivatives. Use of N-L-valinol derivatives results in highly diastereoselective reactions, where the net stereochemical outcome diverges between N-Ts and N-Boc.