2,2-Dimethyl-5-benzyl-oxazolidin-4-on | 717-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 2,2-Dimethyl-5-benzyl-oxazolidin-4-on
• 英文别名: 5-benzyl-2,2-dimethyl-oxazolidin-4-one；5-Benzyl-2,2-dimethyl-1,3-oxazolidin-4-one
• CAS: 717-39-5
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: BFHLIINJXCWHCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-5-benzyl-oxazolidin-4-on 在 4-二甲氨基吡啶 、 (S)-(CF₃)₃-t-BuPHOX 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.5h， 生成 (5R)-3-benzoyl-5-benzyl-2,2-dimethyl-5-prop-2-enyl-1,3-oxazolidin-4-one
  参考文献：
  名称：

  Enantioselective Synthesis of Dialkylated N-Heterocycles by Palladium-Catalyzed Allylic Alkylation

  摘要：

  The enantioselective synthesis of alpha-disubstituted N-heterocyclic carbonyl compounds has been accomplished using palladium-catalyzed allylic alkylation. These catalytic conditions enable access to various heterocycles, such as morpholinone, thiomorpholinone, oxazolidin-4-one, 1,2-oxazepan-3-one, 1,3-oxazinan-4-one, and structurally related lactams, all bearing fully substituted alpha-positions. Broad functional group tolerance was explored at the alpha-position in the morpholinone series. We demonstrate the utility of this method by performing various transformations on our useful products to readily access a number of enantioenriched compounds.

  DOI：

  10.1021/ol503425t
• 作为产物：
  描述：

  苯乙醛 在 硫酸 作用下， 反应 16.0h， 生成 2,2-Dimethyl-5-benzyl-oxazolidin-4-on
  参考文献：
  名称：

  行为举止。4-恶唑酮。

  摘要：

  DOI：

  10.1021/jm00325a019

文献信息

• ENANTIOSELECTIVE SYNTHESIS OF DIALKYLATED N,O-HETEROCYCLES BY PALLADIUM-CATALYZED ALLYLIC ALKYLATION
  申请人：Stoltz Brian M.

  公开号：US20160096810A1

  公开（公告）日：2016-04-07

  This invention provides enantioenriched N,O-heterocyclic compounds with quaternary stereogenic centers and novel methods of preparing the compounds. Methods include the method for the preparation of a compound of formula (I): comprising treating a compound of formula (II): with a transition metal catalyst under alkylation conditions.

  这项发明提供了含有季碳立体中心的手性富集的N,O-杂环化合物以及制备这些化合物的新方法。方法包括制备式(I)化合物的方法：将式(II)化合物在烷基化条件下与过渡金属催化剂处理。
• Enantioselective Synthesis of Dialkylated <i>N</i>-Heterocycles by Palladium-Catalyzed Allylic Alkylation
  作者：Yoshitaka Numajiri、Gonzalo Jiménez-Osés、Bo Wang、K. N. Houk、Brian M. Stoltz

  DOI：10.1021/ol503425t

  日期：2015.3.6

  The enantioselective synthesis of alpha-disubstituted N-heterocyclic carbonyl compounds has been accomplished using palladium-catalyzed allylic alkylation. These catalytic conditions enable access to various heterocycles, such as morpholinone, thiomorpholinone, oxazolidin-4-one, 1,2-oxazepan-3-one, 1,3-oxazinan-4-one, and structurally related lactams, all bearing fully substituted alpha-positions. Broad functional group tolerance was explored at the alpha-position in the morpholinone series. We demonstrate the utility of this method by performing various transformations on our useful products to readily access a number of enantioenriched compounds.
• Behavioral Stimulants. 4-Oxazolidinones
  作者：John B. Bicking、Sara F. Kwong、Michael H. Fisher、William H. Nicholson

  DOI：10.1021/jm00325a019

  日期：1965.1