(4S)-2-methylthiomethyl-4-methyl-1,3-oxazoline | 155049-14-2

• 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)-2-methylthiomethyl-4-methyl-1,3-oxazoline
• 英文别名: 2-methylthiomethyl-4-(S)-methyl-1,3-oxazoline；(4S)-4-methyl-2-(methylsulfanylmethyl)-4,5-dihydro-1,3-oxazole
• CAS: 155049-14-2
• 化学式: C₆H₁₁NOS
• 分子量: 145.225
• InChiKey: LFYZNPALIYBWQH-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  五羰基溴铼(I) 、 (4S)-2-methylthiomethyl-4-methyl-1,3-oxazoline 以 苯 为溶剂， 以88%的产率得到fac-ReBr(CO)3(2-methylthiomethyl-4-(S)-methyl-1,3-oxazoline)
  参考文献：
  名称：

  Synthesis and detailed NMR study of tricarbonylrhenium(I) and trimethylplatinum(IV) halide complexes of 2-methylthiomethyl-4-(S)-methyl-1,3-oxazoline (L). X-ray crystal structure of fac-[ReBr(CO)3L]

  摘要：

  2-Methylthiomethyl-4-(S)-methyl-1,3-oxazoline (L) reacts with the halogenopentacarbonylrhenium(I) and halgenotrimethylplatinum(IV) metal moieties, to form complexes of general formulae fac-[ReX(CO)(3)L] and fac-[PtXMe(3)L] (X = Cl, Br or I) in good yield. Detailed NMR studies reveal the presence of four solution-state diasteroisomers, which differ according to the orientation of the S-Me and oxazole-methyl groups with respect to the halogen. Above ambient temperature, inversion at the S atom causes the epimerisation of pairs of diastereoisomers. The energetics of S inversion in the complexes [ReX(CO)(3)L] (X = Cl, Br or I) were measured by standard (1)H band shape analysis of the variable temperature spectra; energy barriers, Delta G double dagger (298 K), are in the range 67-70 kJ mol(-1). Atropisomerisation occurs over a period of several hours at ca. 350 K, and several weeks at ca. 273 K. Platinum-195 NMR data are reported for the complexes [PtXMe(3)L] (X = Cl, Br or I). (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-328x(97)00530-5
• 作为产物：
  描述：

  L-氨基丙醇 、 (甲基硫代)乙腈 在 zinc(II) chloride 作用下， 以 氯苯 为溶剂， 反应 48.0h， 以82%的产率得到(4S)-2-methylthiomethyl-4-methyl-1,3-oxazoline
  参考文献：
  名称：

  新型含硫和磷的恶唑啉作为配体的不对称催化反应

  摘要：

  描述了同时包含恶唑啉基团和另外的硫或磷供体原子的对映体纯的配体的制备。一步法制得了甲硫基甲基，邻硫代茴香基和噻吩基恶唑啉，并分两步从可商购的起始原料中以高收率制备了邻二苯基膦基苯基恶唑啉。

  DOI：

  10.1016/s0040-4020(01)80795-x

文献信息

• Allen, Joanne V.; Coote, Steven J.; Dawson, Graham J., Journal of the Chemical Society. Perkin transactions I, 1994, # 15, p. 2065 - 2072
  作者：Allen, Joanne V.、Coote, Steven J.、Dawson, Graham J.、Frost, Christopher G.、Martin, Christopher J.、Williams, Jonathon, M.

  DOI：——

  日期：——
• Allen Joanne V., Dawson Graham J., Frost Christopher G., Williams Jonatha+, Tetrahedron, 50 (1994) N 3, S 799-808
  作者：Allen Joanne V., Dawson Graham J., Frost Christopher G., Williams Jonatha+

  DOI：——

  日期：——