(S)-4-iso-propyl-3-(2'-phenylacetyl)-5,5-dimethyloxazolidin-2-one | 311310-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-4-iso-propyl-3-(2'-phenylacetyl)-5,5-dimethyloxazolidin-2-one
• 英文别名: (4S)-N(3)-phenylacetyl-4-isopropyl-5,5-dimethyloxazolidin-2-one；(S)-4-isopropyl-5,5-dimethyl-3-(2-phenylacetyl)oxazolidin-2-one；(4S)-5,5-dimethyl-3-(2-phenylacetyl)-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 311310-12-0
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: NGPKWHDBLHJTHZ-AWEZNQCLSA-N

物化性质

• 沸点：
  410.3±24.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S)-4-iso-propyl-3-(2'-phenylacetyl)-5,5-dimethyloxazolidin-2-one 在 lithium hydroxide monohydrate 、 水 、 双氧水 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.66h， 生成 (S)-2-fluoro-2-phenylacetic acid
  参考文献：
  名称：

  Stereoselective α-Fluorination of N-Acyloxazolidinones at Room Temperature within 1 h

  摘要：

  A direct alpha-fluorination of N-acyloxazolidinones based on the unique reactivity of group IVa metal enolates has been developed. The reaction is an experimentally simple, low-cost, quick, and energy-efficient alternative for asymmetric alpha-fluorination of N-acyloicazolidinones. Preliminary studies have shown compatibility with alkyl, alkenyl, and alkynyl, aromatic, and several heteroaromatic substituents. High diastereoselectivities have been achieved with most substrates tested, and the reaction is typically complete within 1 h at ambient temperature.

  DOI：

  10.1021/jo500957d
• 作为产物：
  描述：

  苯乙酸 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 (S)-4-iso-propyl-3-(2'-phenylacetyl)-5,5-dimethyloxazolidin-2-one
  参考文献：
  名称：

  Stereoselective α-Fluorination of N-Acyloxazolidinones at Room Temperature within 1 h

  摘要：

  A direct alpha-fluorination of N-acyloxazolidinones based on the unique reactivity of group IVa metal enolates has been developed. The reaction is an experimentally simple, low-cost, quick, and energy-efficient alternative for asymmetric alpha-fluorination of N-acyloicazolidinones. Preliminary studies have shown compatibility with alkyl, alkenyl, and alkynyl, aromatic, and several heteroaromatic substituents. High diastereoselectivities have been achieved with most substrates tested, and the reaction is typically complete within 1 h at ambient temperature.

  DOI：

  10.1021/jo500957d

文献信息

• SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
  作者：Steven D. Bull、Stephen G. Davies、A. Christopher Garner、Dennis Kruchinin、Min-Suk Key、Paul M. Roberts、Edward D. Savory、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b605244d

  日期：——

  The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels–Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

  在手性噁唑啉酮的5位引入一个双甲基基团会使得邻近的C(4)立体导向基团倾向于特定构象，即双甲基-4-异丙基的组合能模拟一个C(4)叔丁基基团，从而实现更高的立体控制水平，优于简单的4-异丙基噁唑啉酮。这一原理的普遍性在立体选择性烯醇化物烷基化、动力学拆分、狄尔斯-阿尔德环加成和钯催化的不对称缩醛化反应中得到了应用验证。
• Solution phase structures of enantiopure and racemic lithium N-benzyl-N-(α-methylbenzyl)amide in THF: low temperature 6Li and 15N NMR spectroscopic studies
  作者：Timothy D.W. Claridge、Stephen G. Davies、Dennis Kruchinin、Barbara Odell、Paul M. Roberts、Angela J. Russell、James E. Thomson、Steven M. Toms

  DOI：10.1016/j.tetasy.2013.07.001

  日期：2013.8

  enantiopure ammonia equivalents for the asymmetric synthesis of β-amino acid derivatives via conjugate addition to α,β-unsaturated esters. 6Li and 15N NMR spectroscopic studies of doubly labelled 6lithium (S)-15N-benzyl-15N-(α-methylbenzyl)amide in THF at low temperature reveal the presence of lithium amide dimers as the only observable species. Either a monomeric or dimeric lithium amide reactive species

  N-苄基-N-（α-甲基苄基）酰胺锂的对映体是通过对α，β-不饱和酯进行共轭加成来不对称合成β-氨基酸衍生物的高效对映纯氨当量。双标记6锂（S）-15 N-苄基-15 N的6 Li和15 N NMR谱研究。-（α-甲基苄基）酰胺在低温下的THF溶液中显示出酰胺锂二聚体的存在是唯一可观察到的物质。对于这类共轭加成反应，可以在过渡态助记符中容纳单体或二聚的氨基酰胺锂反应性物质。由于对形成的各种二聚体的容易区分，该对映体纯的氨基酰胺锂与非手性的（例如二苄基氨基化锂）和C 2对称的（例如双-N，N -α-甲基苄基氨基化锂）对应物相比提供了独特的机会，可用于进一步的机理研究。
• Stereoselective α-Fluorination of <i>N</i>-Acyloxazolidinones at Room Temperature within 1 h
  作者：Joseph Alvarado、Aaron T. Herrmann、Armen Zakarian

  DOI：10.1021/jo500957d

  日期：2014.7.3

  A direct alpha-fluorination of N-acyloxazolidinones based on the unique reactivity of group IVa metal enolates has been developed. The reaction is an experimentally simple, low-cost, quick, and energy-efficient alternative for asymmetric alpha-fluorination of N-acyloicazolidinones. Preliminary studies have shown compatibility with alkyl, alkenyl, and alkynyl, aromatic, and several heteroaromatic substituents. High diastereoselectivities have been achieved with most substrates tested, and the reaction is typically complete within 1 h at ambient temperature.