(4R,5S)-(+)-4-Methyl-5-phenyloxazolidine-2-selone | 127399-16-0

• 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: (4R,5S)-(+)-4-Methyl-5-phenyloxazolidine-2-selone
• 英文别名: (4R,5S)-4-methyl-5-phenyl-4,5-dihydro-1,3-oxazole-2-selenol
• CAS: 127399-16-0
• 化学式: C₁₀H₁₁NOSe
• 分子量: 240.163
• InChiKey: QMCBOXILNIZIHG-VXNVDRBHSA-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：

  α-deuterio(phenyl)acetic acid 、 (4R,5S)-(+)-4-Methyl-5-phenyloxazolidine-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 (4R,5S)-3-<2'-(1H,2H)-2'-Phenyl-1-oxoethyl>-4-methyl-5-phenyloxazolidine-2-selone
  参考文献：
  名称：

  Quantitative detection of remotely disposed chiral centers using selenium-77 nuclear magnetic resonance spectroscopy

  摘要：

  DOI：

  10.1021/ja00168a064
• 作为产物：
  描述：

  左旋去甲麻黄碱 在 selenium 、 苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 71.5h， 生成 (4R,5S)-(+)-4-Methyl-5-phenyloxazolidine-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

• Total Synthesis of (+)-Calyculin A and (−)-Calyculin B:  Cyanotetraene Construction, Asymmetric Synthesis of the C(26−37) Oxazole, Fragment Assembly, and Final Elaboration
  作者：Amos B. Smith、Gregory K. Friestad、Joseph Barbosa、Emmanuel Bertounesque、James J.-W. Duan、Kenneth G. Hull、Makoto Iwashima、Yuping Qiu、P. Grant Spoors、Brian A. Salvatore

  DOI：10.1021/ja992135e

  日期：1999.11.1

  asymmetric synthesis of the C(26−37) oxazole, fragment assembly and final elaboration to (+)-1 and (−)-2. Highlights of the synthesis include: application of a one-pot three-component Suzuki reaction for the construction of phosphonate A, a bifunctional triene precursor of the light sensitive C(1−8) cyanotetraene subunit, an asymmetric synthesis of the C(26−32) oxazole (−)-D, exploiting the Silks−Odom

  已经实现了导致 (+)-calyculin A 和 (-)-calyculin B（1 和 2）的收敛全合成，它们是强效、高选择性和显着细胞渗透性磷酸酶抑制剂 calyculin A 和 B 的对映体。在前面的论文中，我们概述了 C(9-25) 螺缩酮二丙酸酯亚基 (+)-BC 的不对称合成；在本文中，我们描述了 C(1-8) 氰基四烯的构建、C(26-37) 恶唑的不对称合成、片段组装以及对 (+)-1 和 (-)-2 的最终阐述。合成的亮点包括：应用一锅三组分 Suzuki 反应构建膦酸酯 A，一种光敏 C(1-8) 氰基四烯亚基的双功能三烯前体，C(26-) 的不对称合成32) 恶唑 (-)-D，利用 Silks-Odom 77Se NMR 协议来评估对映体纯度，
• 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.
• 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).
• Calyculin synthetic studies. 3. Enantiomeric purity determination for the C(26)–C(32) oxazole segment via the silks-odom 77Se NMR method
  作者：Brian A. Salvatore、Amos B. Smith

  DOI：10.1016/s0040-4039(00)76209-5

  日期：1994.2

  An improved preparation of the C(26)-C(32) oxazole subunit of calyculin A is described. The enantiomeric purity was determined via the exceptionally sensitive Silks-Odom method, which can probe remote stereocenters by Se-77 NMR analysis.
• 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：——