(S)-4-(1-Methylethyl)-<2-13C>-2-oxazoline | 157067-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: (S)-4-(1-Methylethyl)-<2-13C>-2-oxazoline
• 英文别名: (4S)-4-propan-2-yl-(213C)4,5-dihydro-1,3-oxazole
• CAS: 157067-85-1
• 化学式: C₆H₁₁NO
• 分子量: 114.148
• InChiKey: FPIBKDDEZCKPGT-WTHMKFHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (S)-4-(1-Methylethyl)-<2-13C>-2-oxazoline 在 lithium hexamethyldisilazane 、 环八硒 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到(S)-(-)-4-(1-Methylethyl)-<2-13C>-oxazolidine-2-selone
  参考文献：
  名称：

  Synthesis of Chiral ¹³C,⁷⁷Se-Labeled Selones

  摘要：

  Stable isotope-labeled N-acyl selones have been constructed in fewer than four steps from readily available starting materials. Site-specific labeling was achieved using the following synthons: bromo [2-C-13] acetic acid, [C-13]formic acid, and elemental Se-77. These labeled selones have been found to provide unique insights into enolate structure and may be useful in the detection and quantitation of remotely disposed chiral centers in compounds in short supply.

  DOI：

  10.1021/jo049747o
• 作为产物：
  描述：

  L-缬氨醇 、 甲酸-13C 反应 0.5h， 以88%的产率得到(S)-4-(1-Methylethyl)-<2-13C>-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

• 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.
• 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 of Chiral ¹³C,⁷⁷Se-Labeled Selones
  作者：Morgane Ollivault-Shiflett、David B. Kimball、L. A. “Pete” Silks

  DOI：10.1021/jo049747o

  日期：2004.7.1

  Stable isotope-labeled N-acyl selones have been constructed in fewer than four steps from readily available starting materials. Site-specific labeling was achieved using the following synthons: bromo [2-C-13] acetic acid, [C-13]formic acid, and elemental Se-77. These labeled selones have been found to provide unique insights into enolate structure and may be useful in the detection and quantitation of remotely disposed chiral centers in compounds in short supply.