(4S)-3-acetoacetyl-4-isopropyl-1,3-oxazolidin-2-one | 96021-70-4

• 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: (4S)-3-acetoacetyl-4-isopropyl-1,3-oxazolidin-2-one
• 英文别名: 1-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-butane-1,3-dione；1-((4S)-4-isopropyl-2-oxooxazolidin-3-yl)butane-1,3-dione；1-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]butane-1,3-dione
• CAS: 96021-70-4
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: FJUOLFQCWAYWMG-MRVPVSSYSA-N

物化性质

• 沸点：
  355.4±25.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (4S)-3-acetoacetyl-4-isopropyl-1,3-oxazolidin-2-one 在 lithium hydroxide 、 4-羧基苯磺叠氮 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 20.17h， 生成 (4S)-N-(diazoacetyl)-4-(2-propyl)oxazolidone
  参考文献：
  名称：

  Synthesis and catalytic reactions of chiral N-(diazoacetyl)oxazolidones

  摘要：

  DOI：

  10.1021/jo00210a020
• 作为产物：
  描述：

  双乙烯酮 、 (S)-4-异丙基-2-唑烷酮 在 正丁基锂 作用下， 生成 (4S)-3-acetoacetyl-4-isopropyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and catalytic reactions of chiral N-(diazoacetyl)oxazolidones

  摘要：

  DOI：

  10.1021/jo00210a020

文献信息

• Electrochemically-initiated Michael addition of chiral acetoacetic derivatives to methyl vinyl ketone: stereocontrolled construction of quaternary carbon centers
  作者：Laura Palombi、Marta Feroci、Monica Orsini、Achille Inesi

  DOI：10.1016/s0957-4166(02)00636-5

  日期：2002.10

  Stereoselective conjugate addition of chiral β-dicarbonyl derivatives to methyl vinyl ketone was promoted by electrolysis, using a catalytic amount of electricity. With respect to the metal-catalyzed methods, the electrochemical, metal-free conditions resulted in enhanced reactivity of the electrogenerated enolates, so that the Michael addition was found to occur under mild conditions and short reaction

  通过催化作用，利用催化量的电，手性β-二羰基衍生物向甲基乙烯基酮的立体选择性共轭加成反应。关于金属催化的方法，电化学，无金属的条件导致电生成的烯醇化物的反应性增强，因此发现迈克尔加成反应在温和的条件下和较短的反应时间下进行，从而提供了具有明显非对映异构体过量的产物。当将Oppolzer的sultam用作手性诱导剂并使用延长的反应时间时，观察到立体选择性的逆转，证明了电化学诱导的加成反应和随后的热力学平衡的动力学控制。基于电化学的方法也被用于精制季生立体碳中心。
• Oxidative asymmetric umpolung alkylation of Evans’ β-ketoimides using dialkylzinc nucleophiles
  作者：Tom A. Targel、Jayprakash N. Kumar、O. Svetlana Shneider、Sukanta Bar、Natalia Fridman、Shimon Maximenko、Alex M. Szpilman

  DOI：10.1039/c4ob02601b

  日期：——

  Umpolung alkylation of Evans’ auxiliary substituted β-ketoimides affords the diastereomerically pure products in yields ranging from 40 to 80%.

  埃文斯辅基取代的β-酮亚胺的反极化烷基化反应可获得对映纯度高的产物，收率在40%到80%之间。
• Electrochemical generation of tetraethylammonium N-acetoacetyloxazolidin-2-one enolates: an easy access to α-alkylated acetoacetic derivatives
  作者：Laura Palombi、Marta Feroci、Monica Orsini、Leucio Rossi、Achille Inesi

  DOI：10.1016/s0040-4039(02)00464-1

  日期：2002.4

  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.
• Highly diastereoselective addition of Et2AlCN to β-keto amides derived from (S)-4-isopropyl-2-oxazolidinone
  作者：Virginia Flores-Morales、Mario Fernández-Zertuche、Mario Ordóñez

  DOI：10.1016/j.tetasy.2003.07.004

  日期：2003.9

  The addition of Et2AlCN in the presence of ZnBr2 or Et2AlCl to 1,3-dicarbonyl compounds derived from (S)-4-isopropyl-2-oxazolidinone, proceeds with high diastereoselectivity (94-98% de) and good chemical yields. This type of addition to chiral P-dicarbonyl substrates represents a new synthetic methodology leading to the formation of enantiomerically pure cyanohydrins. (C) 2003 Elsevier Ltd. All rights reserved.
• Tandem Chain Extension−Aldol Reaction:  Syn Selectivity with a Zinc Enolate
  作者：Sujen Lai、Charles K. Zercher、Jerry P. Jasinski、Seth N. Reid、Richard J. Staples

  DOI：10.1021/ol016788n

  日期：2001.12.1

  [GRAPHICS]A tandem chain extension-aldol reaction was developed in which beta -keto esters are transformed to alpha -substituted-gamma -keto esters in an efficient zinc-mediated, one-pot reaction. The diastereoselectivity of the reaction ranged from good to excellent with syn stereochemistry observed for,8-keto ester and amide substrates and anti-stereochemistry observed for a beta -keto imide.