(4S,5R)-3-<5-(1,2-dithiolan-3-yl)-1-oxopentyl>-4-methyl-5-phenyloxazolidine-2-selone | 138715-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: (4S,5R)-3-<5-(1,2-dithiolan-3-yl)-1-oxopentyl>-4-methyl-5-phenyloxazolidine-2-selone
• 英文别名: (4S,5R)-3-[5-(1,2-dithiolan-3-yl)-1-oxopentyl]-4-methyl-5-phenyloxazolidine-2-selone；5-(dithiolan-3-yl)-1-[(4S,5R)-4-methyl-5-phenyl-2-selanylidene-1,3-oxazolidin-3-yl]pentan-1-one
• CAS: 138715-29-4；138715-30-7
• 化学式: C₁₈H₂₃NO₂S₂Se
• 分子量: 428.478
• InChiKey: ABECDLCSGWAQNA-YRFPZCSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  去甲麻黄碱 在 selenium 、 四丁基氟化铵 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 26.58h， 生成 (4S,5R)-3-<5-(1,2-dithiolan-3-yl)-1-oxopentyl>-4-methyl-5-phenyloxazolidine-2-selone
  参考文献：
  名称：

  Synthesis of (4S,5R)-(–)-4-methyl-5-phenyloxazolidine-2-selone: a chiral auxiliary reagent capable of detecting the enantiomers of (R,S)-lipoic acid by⁷⁷Se nuclear magnetic resonance spectroscopy

  摘要：

  （4S,5R)-(-)-4-甲基-5-苯基恶唑烷-2-硒酮在10克规模下分五步构建而成。硒-77 NMR光谱研究表明，该硒酮作为一种高度敏感的手性辅助剂，能够轻易区分与硒酮偶联的（R,S）-硫辛酸（Δδ 0.119 ppm），即使其手性中心与被观察的核相隔8个键。

  DOI：

  10.1039/p19910002495

文献信息

• 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).
• Synthesis of (4S,5R)-(–)-4-methyl-5-phenyloxazolidine-2-selone: a chiral auxiliary reagent capable of detecting the enantiomers of (R,S)-lipoic acid by⁷⁷Se nuclear magnetic resonance spectroscopy
  作者：Louis A. Silks、Jie Pang、Jerome D. Odom、R. Bruce Dunlap

  DOI：10.1039/p19910002495

  日期：——

  (4S,5R)-(-)-4-Methyl-5-phenyloxazolidine-2-selone was constructed in 5 steps on the 10-gram scale. Se-77 NMR spectroscropic studies revealed that this selone served as a remarkably sensitive chiral auxiliary agent which readily distinguished the selone-coupled (R,S)-lipoic acid (DELTA-delta 0.119 ppm), even though its chiral centre was separated by 8 bonds from the observed nucleus.

  （4S,5R)-(-)-4-甲基-5-苯基恶唑烷-2-硒酮在10克规模下分五步构建而成。硒-77 NMR光谱研究表明，该硒酮作为一种高度敏感的手性辅助剂，能够轻易区分与硒酮偶联的（R,S）-硫辛酸（Δδ 0.119 ppm），即使其手性中心与被观察的核相隔8个键。