(4S,5S)-5-tosyloxymethyl-4-(4-methylthiophenyl)-2-phenyl-2-oxazoline | 263260-09-9

• 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,5S)-5-tosyloxymethyl-4-(4-methylthiophenyl)-2-phenyl-2-oxazoline
• 英文别名: [(4S,5S)-5-(4-methylsulfanylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 263260-09-9
• 化学式: C₂₄H₂₃NO₄S₂
• 分子量: 453.583
• InChiKey: RHYYNPJSMQASRR-GOTSBHOMSA-N

物化性质

• 沸点：
  634.3±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  98.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-tosyloxymethyl-4-(4-methylthiophenyl)-2-phenyl-2-oxazoline 在 titanium(IV) isopropylate 、 L-(+)-酒石酸二乙酯 、 过氧化氢异丙苯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 以66%的产率得到(4S,5S,R_S)-4-tosyloxymethyl-5-(4-methylsulfinylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  S-Oxidation products of (+)-thiomicamine-derived oxazolines—promising substrates in the synthesis of alkyl methyl sulfoxides

  摘要：

  Highly stereoselective oxidation of the 4-methylthio substituent in oxazolines 2-4, derived from (+)-thiomicamine 1, performed using the Kagan procedure and with the vanadium/chiral salen catalytic system, afforded R-s and S-s diastereomeric sulfoxides 5-7, respectively. The reaction of sulfoxide R-s-6 with n-butyl- and tert-butyllithium reagents produced the corresponding butyl methyl sulfoxides in high enantiomeric excess and with an (S) absolute configuration, albeit in moderate yields. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.027
• 作为产物：
  描述：

  对甲苯磺酰氯 、 [(4S,5S)-5-(4-methylsulfanylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol 在 吡啶 作用下， 反应 48.0h， 以92.6%的产率得到(4S,5S)-5-tosyloxymethyl-4-(4-methylthiophenyl)-2-phenyl-2-oxazoline
  参考文献：
  名称：

  Transformation of (+)-thiomicamine into a new ligand for the enantioselective addition of methyllithium to prochiral imines

  摘要：

  A new ligand 2 was prepared from (+)-thiomicamine 1 and o-methoxyphenol, and its activity as an external controller of stereochemistry in enantioselective additions of methyllithium to prochiral imines 8-10 tested. The non-racemic secondary amines 11-13 were prepared in 60-90% chemical yield with the enantioselectivity ranging from 2 to 41%. 6,7-Dimethoxy-3,4-dihydroisoquinoline 8 was transformed into (+)-salsolidine 11 with an e.e. of 41%. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00573-x

文献信息

• Enantioselective addition of methyllithium to a prochiral imine—the substrate in the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline derivatives mediated by chiral monooxazolines
  作者：Agata Głuszyńska、Maria D. Rozwadowska

  DOI：10.1016/j.tetasy.2004.08.011

  日期：2004.10

  monooxazoline ligands 7–24 with substituents at C-2 and C-4, differing in electronic and steric properties, has been synthesized from (+)-thiomicamine 6. The effect of the oxazoline structure on the course of addition of methyllithium to imine 1 has been studied. The addition product, amine 3, which is the key intermediate in the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline derivatives, has

  一系列手性monooxazoline的配体7 - 24 thiomicamine -在C-2和C-4具有取代基时，在电子和空间性质不同，已经从（+）合成6。已经研究了恶唑啉结构对向亚胺1添加甲基锂的过程的影响。加成产物胺3是四氢异喹啉衍生物在Pomeranz-Fritsch-Bobbitt合成中的关键中间体，已获得了高收率（92％）和ee高达76％。
• Kowalczyk; Skarzewski, Polish Journal of Chemistry, 2007, vol. 81, # 11, p. 1987 - 1999
  作者：Kowalczyk、Skarzewski

  DOI：——

  日期：——