5-methyl-5-[(methylphenylamino)methyl]-2(5H)-furanone

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-methyl-5-[(methylphenylamino)methyl]-2(5H)-furanone
• 英文别名: 5-methyl-5-[(N-methylanilino)methyl]furan-2-one
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: ZXJMHZFHQBEVAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二甲基苯胺 、 triisopropyl((5-methylfuran-2-yl)oxy)silane 在 叔丁基过氧化氢 、 dirhodium(II) tetrakis(caprolactam) 作用下， 以 甲醇 为溶剂， 以72%的产率得到5-methyl-5-[(methylphenylamino)methyl]-2(5H)-furanone
  参考文献：
  名称：

  The Oxidative Mannich Reaction Catalyzed by Dirhodium Caprolactamate

  摘要：

  Dirhodium caprolactamate [Rh2(cap)4] is a highly effective catalyst for the oxidative Mannich reaction. The reaction proceeds via C-H oxidation of a tertiary amine followed by nucleophilic capture. This green transformation is conducted in protic solvent using inexpensive T-HYDRO (70% t-BuOOH in water). Synthetically valuable gamma-aminoalkyl butenolides are obtained.

  DOI：

  10.1021/ja061146m

文献信息

• Allylic Oxidations Catalyzed by Dirhodium Catalysts under Aqueous Conditions
  申请人：Doyle Michael P.

  公开号：US20090093638A1

  公开（公告）日：2009-04-09

  The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers.

  本发明涉及在水相条件下实现有机分子的高效烯丙基氧化的组合物和方法，特别是烯烃和类固醇。该发明涉及使用二铑（II,II）“桨轮”配合物，特别是二铑羧酸酯和叔丁基过氧化氢作为催化剂进行反应。在烯丙基氧化7-酮类固醇中使用水相条件特别有优势，无法使用无水方法有效氧化，以及将烯丙基氧化扩展到烯酰胺和烯醇醚。
• The Oxidative Mannich Reaction Catalyzed by Dirhodium Caprolactamate
  作者：Arthur J. Catino、Jason M. Nichols、Brian J. Nettles、Michael P. Doyle

  DOI：10.1021/ja061146m

  日期：2006.5.1

  Dirhodium caprolactamate [Rh2(cap)4] is a highly effective catalyst for the oxidative Mannich reaction. The reaction proceeds via C-H oxidation of a tertiary amine followed by nucleophilic capture. This green transformation is conducted in protic solvent using inexpensive T-HYDRO (70% t-BuOOH in water). Synthetically valuable gamma-aminoalkyl butenolides are obtained.
• US8163944B2
  申请人：——

  公开号：US8163944B2

  公开（公告）日：2012-04-24
• Highly efficient Cu-catalyzed oxidative coupling of tertiary amines and siloxyfurans
  作者：Youming Shen、Ze Tan、De Chen、Xunbo Feng、Mo Li、Can-Cheng Guo、Chengliang Zhu

  DOI：10.1016/j.tet.2008.10.078

  日期：2009.1

  A mild, selective, and efficient protocol for the synthesis of gamma-aminoalkyl butenolides via the oxidative coupling between tertiary amines and siloxyfurans catalyzed by simple copper salts was developed. Compared with the reported method, our method employs copper catalyst instead of the expensive rhodium catalyst. Besides TBHP, both O-2 and H2O2 can also be utilized as oxidant to effect the coupling. (C) 2008 Elsevier Ltd. All rights reserved.