(4S)-4-(2-methylpropyl)-4,5-dihydro-1,3-oxazole | 136794-50-8

• 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: (4S)-4-(2-methylpropyl)-4,5-dihydro-1,3-oxazole
• CAS: 136794-50-8
• 化学式: C₇H₁₃NO
• 分子量: 127.186
• InChiKey: MDLMKSIXYGOUEX-ZETCQYMHSA-N

物化性质

• 沸点：
  156.3±23.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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)-4-(2-methylpropyl)-4,5-dihydro-1,3-oxazole 在 selenium 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 以90%的产率得到(S)-(-)-(2-Methylpropyl)oxazolidine-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：

  N,N-二甲基甲酰胺二甲基缩醛 生成 (4S)-4-(2-methylpropyl)-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Peng Jie, Barr Mary E., Ashburn David A., Odom Jerome D., Dunlap R. Bruce+, J. Org. Chem, 59 (1994) N 17, S 4977-4987

  摘要：

  DOI：

文献信息

• Chiral Boron-Bridged Bisoxazoline (Borabox) Ligands: Structures and Reactivities of Pd and Cu Complexes
  作者：Valentin Köhler、Clément Mazet、Aurélie Toussaint、Klaus Kulicke、Daniel Häussinger、Markus Neuburger、Silvia Schaffner、Stefan Kaiser、Andreas Pfaltz

  DOI：10.1002/chem.200800822

  日期：2008.9.26

  92:8 mixture of (syn,syn) and (anti,syn) allyl isomers, in contrast with a previously reported box analogue that existed exclusively in the (syn,syn) form. Comparison of the corresponding crystal structures revealed that the distance between the bisoxazoline and the allyl ligand in the borabox complex is shorter. In the copper-catalyzed allylic oxidation of cyclohexene and cyclopentene with tert-butyl

  阴离子硼桥联的双恶唑啉（硼砂箱配体）已合成并以质子化形式表征。配体可在很宽的范围内调节，从而在恶唑啉环和中心桥连的硼原子上允许烷基或芳基取代基。这种新的配体类型的结构参数已通过X射线分析钯和铜配合物进行了研究。已经通过（13）C NMR光谱和通过DFT计算对钯烯丙基配合物研究了电子性质，并将其与类似的双恶唑啉（盒）配合物进行了比较。Borabox配合物在金属中心比中性盒同类物更富电子，由于桥接原子和恶唑啉环之间键长的缘故，它们的咬合角更大。带有未取代的烯丙基配体的钯（II）配合物和均配铜（II）配合物均具有几乎平坦的螯合环。（1,3-二苯基烯丙基）（硼箱）钯配合物的NMR分析表明，（syn，syn）和（反，syn）烯丙基异构体为92：8的混合物，与之前报道的仅存在于该化合物中的盒式类似物相反（syn，syn）形式。对相应晶体结构的比较表明，硼砂箱配合物中双恶唑啉与烯丙基配体之间的距离更短。
• 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.