1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-methylbutane-1,3-dione | 220560-01-0

• 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: 1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-methylbutane-1,3-dione
• CAS: 220560-01-0
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: RASSFVGROJAAET-HQVZTVAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-methylbutane-1,3-dione 在 甲烷磺酸 、 一水合肼 作用下， 以 乙二醇二甲醚 为溶剂， 以46%的产率得到(4S)-4-Benzyl-3-(3(5),4-dimethyl-5(3)-pyrazolyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Reaction of Hydrazines with N-Acetoacetyl Derivatives of (4S)-4-Benzyloxazolidin-2-one and (2R)-Bornane-10,2-sultam in Very Acidic Media to Give Pyrazoles Retaining the Chiral Moiety at C-3(5)

  摘要：

  肼与乙酰乙酰胺反应生成保留胺分子的吡唑。Evans oxazolidinone 和 Oppolzer sultam 已被并入吡唑中。

  DOI：

  10.1055/s-1999-3683
• 作为产物：
  描述：

  1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-butane-1,3-dione 、 碘甲烷 在 高氯酸四乙基铵 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以70%的产率得到1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-2-methylbutane-1,3-dione
  参考文献：
  名称：

  Electrochemical generation of tetraethylammonium N-acetoacetyloxazolidin-2-one enolates: an easy access to α-alkylated acetoacetic derivatives

  摘要：

  A new electrochemical method for the mild generation of naked beta-dicarbonyl derivative enolates is disclosed. The electrolysis, under galvanostatic control. of a solution of N-acetoacetyloxazolidin-2-ones acetonitrile tetraethylammonium perchlorate allowed the selective alpha-monoalkylation of the 1.3-dicarbonyl residue with a variety of alkyl halides, in very good yields and short reaction times. More interestingly. no by-products arising from either the electroreduction of the carbonyl functionalities or from nucleophilic cyanomethyl anion attack were detected. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00464-1

文献信息

• Dimethoxyethane as an Alternative Solvent for Schmidt Reactions. Preparation of Homochiral N-(5-Oxazolyl)oxazolidinones from N-Acetoacetyl Derivatives of Oxazolidinones
  作者：Nicanor Gálvez、Marcial Moreno-Mañas、Rosa M. Sebastián、Adelina Vallribera

  DOI：10.1016/0040-4020(95)00989-2

  日期：1996.1

  Dimethoxyethane is an useful solvent for the Schmidt reaction of ketones and β-ketoesters with sodium azide and methanesulfonic acid to afford amides and amidoesters. This solvent is an alternative to the unsafe chlorinated solvents normally used. A β-diketone and several (4S)-N-(2-alkylacctoacetyl)-4-benzyloxazolidin-2-ones afford oxazoles under those conditions.

  二甲氧基乙烷是酮和β-酮​​酸酯与叠氮化钠和甲磺酸进行Schmidt反应以生成酰胺和酰胺基酯的有用溶剂。该溶剂是通常使用的不安全氯化溶剂的替代品。在这些条件下，β-二酮和几个（4S）-N-（2-烷基乙酰乙酰基）-4-苄基恶唑烷-2-酮可提供恶唑。
• Michael additions catalyzed by phosphines. An overlooked synthetic method
  作者：Carolina Gimbert、Maria Lumbierres、Caroline Marchi、Marcial Moreno-Mañas、Rosa M. Sebastián、Adelina Vallribera

  DOI：10.1016/j.tet.2005.07.005

  日期：2005.9

  Triphenylphosphine and tributylphosphine are excellent catalysts for Michael additions. Many beta-dicarbonyl compounds and electron-poor olefins, including sterically demanding partners, react successfully. The Michael addition catalyzed by phosphines deserves attention in its own right as a useful synthetic method. (c) 2005 Elsevier Ltd. All rights reserved.