(4S,5R)-(+)-4,5-Diphenyloxazolidine-2-selone | 136794-55-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4S,5R)-(+)-4,5-Diphenyloxazolidine-2-selone
• 英文别名: (4S,5R)-4,5-diphenyl-4,5-dihydro-1,3-oxazole-2-selenol
• CAS: 136794-55-3
• 化学式: C₁₅H₁₃NOSe
• 分子量: 302.234
• InChiKey: KMSOJSDKNPERNH-UONOGXRCSA-N

物化性质

• 沸点：
  390.1±52.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苯基丙酰氯 、 (4S,5R)-(+)-4,5-Diphenyloxazolidine-2-selone 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4S,5R)-3-(1-Oxo-2-phenylpropyl)-4,5-diphenyloxazolidine-2-selone
  参考文献：
  名称：

  Synthesis and Characterization of Acylated Chiral Oxazolidine-2-selones: Selone Chiral Derivatizing Agents for the Detection and Quantitation of Remotely Disposed Chiral Centers

  摘要：

  Racemic and chiral carboxylic acids and acid chlorides are coupled cleanly to oxazolidine-2-selone chiral derivatizing agents (CDA's) with yields ranging from 85 to 99%. Se-77 NMR spectroscopy provides a highly sensitive method for the determination of the enantiomeric excesses of these remotely disposed chiral centers. The geometrical relationship between the selenocarbonyl and the adduct carbonyl (syn or anti) appears to have a profound effect on the chemical shift difference (Delta delta(Se)) observed for pairs of adduct diastereomers. Crystallographic and solution state NMR studies suggest that the syn orbital overlap enhances the Delta delta(Se).

  DOI：

  10.1021/jo00122a039
• 作为产物：
  描述：

  cis-4,5-diphenyl-4,5-dihydro-oxazole 在 selenium 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以83%的产率得到(4S,5R)-(+)-4,5-Diphenyloxazolidine-2-selone
  参考文献：
  名称：

  Synthesis and Characterization of Chiral Oxazolidine-2-selones: A General One-Step Procedure from Readily Available Oxazolines

  摘要：

  The synthesis of a wide variety of chiral oxazolidine-2-selones from readily available 2-oxazolines has been accomplished in one step with yields ranging from 82 to 98%. A mechanistic investigation of the formation of these selones has indicated the presence of intermediate anions which have been characterized by C-13 and Se-77 NMR spectroscopy. X-ray crystallographic data suggest the chiral selones exists as dimeric pairs or networks linked by unusual selenium hydrogen bonds. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful fdr the detection and quantitation of chirality at remotely disposed chiral centers.

  DOI：

  10.1021/jo00096a048

文献信息

• An improved synthesis of chiral oxazolidine-2-selones: highly sensitive selenium-77 NMR reagents for the detection and quantitation of chirality
  作者：Louis A. Silks、Jie Peng、Jerome D. Odom、R. Bruce Dunlap

  DOI：10.1021/jo00024a003

  日期：1991.11

  The synthesis of the title compounds from readily available oxazolines has been accomplished in one step in high yield. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful for the detection and quantitation of chirality at remotely disposed chiral centers.
• Peng Jie, Barr Mary E., Ashburn David A., Odom Jerome D., Dunlap R. Bruce+, J. Org. Chem, 59 (1994) N 17, S 4977-4987
  作者：Peng Jie, Barr Mary E., Ashburn David A., Odom Jerome D., Dunlap R. Bruce+

  DOI：——

  日期：——
• Synthesis and Characterization of Chiral Oxazolidine-2-selones: A General One-Step Procedure from Readily Available Oxazolines
  作者：Jie Peng、Mary E. Barr、David A. Ashburn、Jerome D. Odom、R. Bruce Dunlap、Louis A. Silks

  DOI：10.1021/jo00096a048

  日期：1994.8

  The synthesis of a wide variety of chiral oxazolidine-2-selones from readily available 2-oxazolines has been accomplished in one step with yields ranging from 82 to 98%. A mechanistic investigation of the formation of these selones has indicated the presence of intermediate anions which have been characterized by C-13 and Se-77 NMR spectroscopy. X-ray crystallographic data suggest the chiral selones exists as dimeric pairs or networks linked by unusual selenium hydrogen bonds. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful fdr the detection and quantitation of chirality at remotely disposed chiral centers.
• Synthesis and Characterization of Acylated Chiral Oxazolidine-2-selones: Selone Chiral Derivatizing Agents for the Detection and Quantitation of Remotely Disposed Chiral Centers
  作者：Jie Peng、Mary E. Barr、David A. Ashburn、Lukasz Lebioda、Albert R. Garber、Rodolfo A. Martinez、Jerome D. Odom、R. Bruce Dunlap、Louis A. Silks

  DOI：10.1021/jo00122a039

  日期：1995.9

  Racemic and chiral carboxylic acids and acid chlorides are coupled cleanly to oxazolidine-2-selone chiral derivatizing agents (CDA's) with yields ranging from 85 to 99%. Se-77 NMR spectroscopy provides a highly sensitive method for the determination of the enantiomeric excesses of these remotely disposed chiral centers. The geometrical relationship between the selenocarbonyl and the adduct carbonyl (syn or anti) appears to have a profound effect on the chemical shift difference (Delta delta(Se)) observed for pairs of adduct diastereomers. Crystallographic and solution state NMR studies suggest that the syn orbital overlap enhances the Delta delta(Se).