(5S)‐5‐methyl‐4‐methylene‐5‐(3‐oxobutyl)‐3‐((S)‐1‐phenylethyl)oxazolidin‐2‐one | 934196-34-6

• 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: (5S)‐5‐methyl‐4‐methylene‐5‐(3‐oxobutyl)‐3‐((S)‐1‐phenylethyl)oxazolidin‐2‐one
• 英文别名: (5S)-5-methyl-4-methylidene-5-(3-oxobutyl)-3-[(1S)-1-phenylethyl]-1,3-oxazolidin-2-one
• CAS: 934196-34-6
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: NJHZAJLMXQBZCF-GUYCJALGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)‐5‐methyl‐4‐methylene‐5‐(3‐oxobutyl)‐3‐((S)‐1‐phenylethyl)oxazolidin‐2‐one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以96%的产率得到(5S)-5-methyl-5-(3-oxobutyl)-3-[(1S)-1-phenylethyl]-1,3-oxazolidine-2,4-dione
  参考文献：
  名称：

  Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides

  摘要：

  A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available alpha-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized alpha-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of alpha-hydroxyamides bearing a quaternary stereocenter were obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.034
• 作为产物：
  描述：

  (S)-(-)-1-苯乙基异氰酸酯 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 73.5h， 生成 (5S)‐5‐methyl‐4‐methylene‐5‐(3‐oxobutyl)‐3‐((S)‐1‐phenylethyl)oxazolidin‐2‐one 、 (5R)‐5‐methyl‐4‐methylene‐5‐(3‐oxobutyl)‐3‐((S)‐1‐phenylethyl)oxazolidin‐2‐one
  参考文献：
  名称：

  对映体纯的4-恶唑啉-2-酮和4-亚甲基-2-恶唑烷酮作为手性结构单元，在杂环的不对称合成中发散。

  摘要：

  对映体纯3 - （（- [R ）-和3 - （（小号）-1-苯乙基）-4-恶唑啉-2-酮被评价为与立体异构源中心的季杂环的发散结构的手性结构单元的。ñ - （[R）-或N-（S）这些化合物的-1-苯乙基被证明是通过热和MW促进的亲核共轭除Michael受体而非对称地诱导4-恶唑啉-2-酮环的4位和5位的有效手性助剂和烷基卤。最终的加合物通过级联过程转化为稠合的六元碳环和杂环。反应产物的结构取决于所用的亲电子试剂和反应条件。替代性的异构体4-亚甲基-2-恶唑烷酮用作手性前体，可用于对高度取代的环状氨基甲酸酯进行灵活多样的处理。DFT量子计算表明，双环吡喃基化合物的形成是由非对映选择性协同杂Diels-Alder环加成反应产生的。

  DOI：

  10.1002/chir.23109

文献信息

• Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides
  作者：Omar Merino、Blanca M. Santoyo、Luisa E. Montiel、Hugo A. Jiménez-Vázquez、L. Gerardo Zepeda、Joaquín Tamariz

  DOI：10.1016/j.tetlet.2010.05.034

  日期：2010.7

  A new approach to the synthesis of 1,3-oxazolidine-2,4-diones, via a two-step reaction sequence, starting from the readily available alpha-ketols and isocyanates, is reported. The condensation of the latter led to the key precursors 4-methylene-2-oxazolidinones, which are converted into the diones by an oxidative cleavage of the exocyclic double bond. Thus, 5,5-disubstituted 1,3-oxazolidine-2,4-diones can be accessed in good yields from the appropriate functionalized alpha-ketols. Moreover, two alternative routes are also described either by functionalization of 4-oxazolin-2-ones or by alkylation of the 1,3-oxazolidine-2,4-dione core previously prepared. Upon hydrolysis of the 1,3-oxazolidine-2,4-diones, a series of alpha-hydroxyamides bearing a quaternary stereocenter were obtained. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantiopure 4‐oxazolin‐2‐ones and 4‐methylene‐2‐oxazolidinones as chiral building blocks in a divergent asymmetric synthesis of heterocycles
  作者：Blanca M. Santoyo、Carlos González‐Romero、Daniel Zárate‐Zárate、R. Israel Hernández‐Benitez、Vanessa Pelayo、Edson Barrera、Carlos H. Escalante、Aydeé Fuentes‐Benites、Guadalupe Martínez‐Morales、Julio López、Miguel A. Vázquez、Francisco Delgado、Hugo A. Jiménez‐Vázquez、Joaquín Tamariz

  DOI：10.1002/chir.23109

  日期：2019.9

  conjugated addition to Michael acceptors and alkyl halides. The resulting adducts were transformed via a cascade process into fused six‐membered carbo‐ and heterocycles. The structure of the reaction products depended on the electrophiles and reaction conditions used. Alternative isomeric 4‐methylene‐2‐oxazolidinones served as chiral precursors for a versatile and divergent approach to highly substituted

  对映体纯3 - （（- [R ）-和3 - （（小号）-1-苯乙基）-4-恶唑啉-2-酮被评价为与立体异构源中心的季杂环的发散结构的手性结构单元的。ñ - （[R）-或N-（S）这些化合物的-1-苯乙基被证明是通过热和MW促进的亲核共轭除Michael受体而非对称地诱导4-恶唑啉-2-酮环的4位和5位的有效手性助剂和烷基卤。最终的加合物通过级联过程转化为稠合的六元碳环和杂环。反应产物的结构取决于所用的亲电子试剂和反应条件。替代性的异构体4-亚甲基-2-恶唑烷酮用作手性前体，可用于对高度取代的环状氨基甲酸酯进行灵活多样的处理。DFT量子计算表明，双环吡喃基化合物的形成是由非对映选择性协同杂Diels-Alder环加成反应产生的。