(4S,5R)-4-methyl-5-phenyl-2-oxazoline | 132486-41-0

• 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: (4S,5R)-4-methyl-5-phenyl-2-oxazoline
• 英文别名: 4(S)-methyl-5(R)-phenyl-2-oxazoline；4(S)-methyl-5(R)-phenyloxazoline；4-Methyl-5-phenyl-2-oxazolin；(4S,5R)-4-methyl-5-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 132486-41-0
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: DFLWPCGUQXZEJK-WPRPVWTQSA-N

物化性质

• 沸点：
  247.6±43.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 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：

  (4S,5R)-4-methyl-5-phenyl-2-oxazoline 在 selenium 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以99%的产率得到(4S,5R)-4-methyl-5-phenyl-oxazolidin-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
• 作为产物：
  描述：

  去甲麻黄碱 、 N,N-二甲基甲酰胺二甲基缩醛 在 苯磺酸 作用下， 以 苯 为溶剂， 反应 70.0h， 以84%的产率得到(4S,5R)-4-methyl-5-phenyl-2-oxazoline
  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

• Stereoselectivity in Aldol Reactions of Chiral N-Acyl Selones
  作者：Zizhong Li、Ruilian Wu、Ryszard Michalczyk、R. Bruce Dunlap、Jerome D. Odom、Louis A. “Pete” Silks

  DOI：10.1021/ja992702y

  日期：2000.1.1

  Aldol reactions have played a central role in many stereoselective constructions of carbon-carbon bonds. During the past several years the selenocarbonyl group has been used both as a chiral interrogation tool (using sup 77} SeNMR spectroscopy) and as a platform for the development of new chemical methods associated with selone based chiral derivatizing agents. During the course of these studies the

  羟醛反应在碳-碳键的许多立体选择性结构中发挥了核心作用。在过去几年中，硒羰基既被用作手性询问工具（使用 sup 77} SeNMR 光谱），也被用作开发与基于 selone 的手性衍生剂相关的新化学方法的平台。在这些研究过程中，作者发现了一种使用手性 selone 试剂的新型羟醛反应，其中硒羰基在确定这些反应的立体选择性方面起着关键作用。本报告描述了涉及使用 N-酰基-oxaxolidin-2-selones 与各种醛的钛 (IV) 烯醇化物的研究结果。
• An Efficient and Versatile Method for the Synthesis of Optically Active 2-Oxazolines: An Acid-catalyzed Condensation of Ortho Esters with Amino Alcohols
  作者：Kazuyuki Kamata、Isao Agata、A. I. Meyers

  DOI：10.1021/jo971161x

  日期：1998.5.1
• 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.
• A rapid and efficient synthesis of chiral 2-hydro-2-oxazolines
  作者：William R. Leonard、Jeffrey L. Romine、A. I. Meyers

  DOI：10.1021/jo00005a059

  日期：1991.3
• LEONARD, WILLIAM R.;ROMINE, JEFFREY L.;MEYERS, A. I., J. ORG. CHEM., 56,(1991) N, C. 1961-1963
  作者：LEONARD, WILLIAM R.、ROMINE, JEFFREY L.、MEYERS, A. I.

  DOI：——

  日期：——