(4S,5R)-4-methyl-5-phenyl-oxazolidin-2-selone | 138715-28-3

• 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: (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-selone
• 英文别名: (4S,5R)-(-)-4-Methyl-5-phenyloxazolidine-2-selone；(4S,5R)-4-methyl-5-phenyl-4,5-dihydro-1,3-oxazole-2-selenol
• CAS: 138715-28-3
• 化学式: C₁₀H₁₁NOSe
• 分子量: 240.163
• InChiKey: QMCBOXILNIZIHG-CBAPKCEASA-N

物化性质

• 沸点：
  304.0±45.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  Boc-L-蛋氨酸 、 (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-selone 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  selone手性衍生剂用于立体构型中心的绝对构型分配中。

  摘要：

  手性selone，手性衍生剂与D和L氨基酸的偶合，得到加合物，其特征在于77 Se NMR，UV和圆二色性光谱，并可以确定母体氨基酸的绝对构型。

  DOI：

  10.1016/0957-4166(94)80066-9
• 作为产物：
  描述：

  去甲麻黄碱 在 selenium 、 四丁基氟化铵 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 25.58h， 生成 (4S,5R)-4-methyl-5-phenyl-oxazolidin-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

• Simple enantiomeric excess determination of alcohols using chiral selones and 77Se NMR spectroscopy
  作者：Ruilian Wu、Jerome D. Odom、R. Bruce Dunlap、Louis A. Silks

  DOI：10.1016/0957-4166(95)00081-y

  日期：1995.4

  Coupling of a chiral selone derivatizing agent to chiral and racemic alcohols mediated with triphosgene gives adducts in yields ranging from 78–100%. 77Se NMR spectroscopy conveniently allows the determination of the enantiomeric excesses of the parent chiral alcohol.

  将手性selone衍生剂与由三光气介导的手性和外消旋醇偶联可得到加合物，收率范围为78–100％。77 Se NMR光谱可以方便地测定母体手性醇的对映体过量。
• 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.
• Reaction of alcohols (via the Mitsunobu reaction) and alkyl halides with chiral selone derivatizing agents
  作者：Ruilian Wu、Jerome D Odom、R.Bruce Dunlap、Louis A Silks

  DOI：10.1016/s0957-4166(99)00140-8

  日期：1999.4

  Coupling of a selone chiral derivatizing agent (CDA) to D,L-alkyl halides gives Se-alkylated adducts in yields ranging from 76-97%. Reaction of D,L-alcohols with the selone CDAs via the Mitsunobu reaction has given rise to Se-alkylated adducts in yields ranging from 82-92%. Examination of the Se-77 NMR spectra of the resulting diastereomeric adducts indicates that discrimination of remotely disposed chiral centers is possible using this technique. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Asymmetric Synthesis of α-Alkylated Aldehydes using Terminal Epoxide-Derived Chiral Enamines
  作者：David M. Hodgson、Naeem S. Kaka

  DOI：10.1002/anie.200804369

  日期：2008.12.8
• 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.