(Z)-1-butyl-4-(2-morpholin-4-yl-2-oxoethylidene)-3-oxa-1-azaspiro[4.5]decan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (Z)-1-butyl-4-(2-morpholin-4-yl-2-oxoethylidene)-3-oxa-1-azaspiro[4.5]decan-2-one
• 英文别名: (4Z)-1-butyl-4-(2-morpholin-4-yl-2-oxoethylidene)-3-oxa-1-azaspiro[4.5]decan-2-one
• 化学式: C₁₈H₂₈N₂O₄
• 分子量: 336.431
• InChiKey: YFZKTRLFGRDSHG-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  炔环己醇 在 magnesium(II) perchlorate 、 air 、 potassium iodide 、 copper(l) chloride 、 palladium(II) iodide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 8.0h， 生成 (Z)-1-butyl-4-(2-morpholin-4-yl-2-oxoethylidene)-3-oxa-1-azaspiro[4.5]decan-2-one
  参考文献：
  名称：

  An Unprecedented Pd-Catalyzed, Water-Promoted Sequential Oxidative Aminocarbonylation−Cyclocarbonylation Process Leading to 2-Oxazolidinones

  摘要：

  An unprecedented, PdI2-catalyzed, sequential oxidative aminocarbonylation-cyclocarbonylation process, leading to 2-oxazolidinone derivatives 3 in good to excellent yields starting from readily available alpha,alpha-disubstituted 2-ynylamines 1 and secondary amines 2, is reported. In the case of an alpha-monosubstituted substrate, the initially formed 2-oxazolidinone derivative underwent shift of the double bond to give a 3H-oxazol-2-one derivative in excellent isolated yield.

  DOI：

  10.1021/ol071332c

文献信息

• Auto-Tandem Catalysis in Ionic Liquids: Synthesis of 2-Oxazolidinones by Palladium-Catalyzed Oxidative Carbonylation of Propargylic Amines in EmimEtSO4
  作者：Raffaella Mancuso、Asif Maner、Ida Ziccarelli、Christian Pomelli、Cinzia Chiappe、Nicola Della Ca’、Lucia Veltri、Bartolo Gabriele

  DOI：10.3390/molecules21070897

  日期：——

  2-oxazolidinone derivatives carried out using an ionic liquid (1-ethyl-3-methylimidazolium ethyl sulfate, EmimEtSO₄) as the solvent is presented. It is based on the sequential concatenation of two catalytic cycles, both catalyzed by the same metal species (auto-tandem catalysis): the first cycle corresponds to the oxidative monoaminocarbonylation of the triple bond of propargylic amines to give the corresponding

  提出了使用离子液体（1-乙基-3-甲基咪唑鎓硫酸乙酯，EmimEtSO 3）作为溶剂对2-恶唑烷酮衍生物进行便利的羰基化方法。它基于两个催化循环的顺序串联，两个催化循环均由相同的金属物种催化（自动串联催化）：第一个循环对应于炔丙基胺的三键的氧化单氨基羰基化，生成相应的2-酰胺中间体。而第二种涉及后者的环羰基化反应，生成2-（2-氧代恶唑烷丁-5-亚烷基）-乙酰胺。使用由PdI 2和过量的KI组成的简单催化体系进行反应
• An Unprecedented Pd-Catalyzed, Water-Promoted Sequential Oxidative Aminocarbonylation−Cyclocarbonylation Process Leading to 2-Oxazolidinones
  作者：Bartolo Gabriele、Pierluigi Plastina、Giuseppe Salerno、Raffaella Mancuso、Mirco Costa

  DOI：10.1021/ol071332c

  日期：2007.8.1

  An unprecedented, PdI2-catalyzed, sequential oxidative aminocarbonylation-cyclocarbonylation process, leading to 2-oxazolidinone derivatives 3 in good to excellent yields starting from readily available alpha,alpha-disubstituted 2-ynylamines 1 and secondary amines 2, is reported. In the case of an alpha-monosubstituted substrate, the initially formed 2-oxazolidinone derivative underwent shift of the double bond to give a 3H-oxazol-2-one derivative in excellent isolated yield.