(4S,5S)-4-Methoxymethyl-5-(4-methylsulfanyl-phenyl)-2-phenyl-4,5-dihydro-oxazole | 290810-34-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4S,5S)-4-Methoxymethyl-5-(4-methylsulfanyl-phenyl)-2-phenyl-4,5-dihydro-oxazole
• 英文别名: (4S,5S)-4-(methoxymethyl)-5-(4-methylsulfanylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 290810-34-3
• 化学式: C₁₈H₁₉NO₂S
• 分子量: 313.42
• InChiKey: NXNNDOTYPJFYOU-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  56.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-Methoxymethyl-5-(4-methylsulfanyl-phenyl)-2-phenyl-4,5-dihydro-oxazole 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， 生成 (4S,5S,S_S)-4-methoxymethyl-5-(4-methylsulfinylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazole 、 (4S,5S,R_S)-4-methoxymethyl-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：

  [(4S,5S)-5-(4-methylsulfanylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]methanol 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以91%的产率得到(4S,5S)-4-Methoxymethyl-5-(4-methylsulfanyl-phenyl)-2-phenyl-4,5-dihydro-oxazole
  参考文献：
  名称：

  Enantioselective modification of the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline alkaloids synthesis of (−)-salsolidine and (−)-carnegine

  摘要：

  (-)-Salsolidine 7 和 (-)-carnegine 8 分别以 46% 和 36% 的对映体过量百分比（e.e.）制备而成。该过程通过在配体 9-12 存在下，将甲基锂选择性地添加到 Pomeranz-Fritsch 亚胺 13 中，随后经酸催化的环化和氢解反应完成。© 2000 Elsevier Science Ltd，版权所有。

  DOI：

  10.1016/s0957-4166(00)00196-8

文献信息

• S-Oxidation products of (+)-thiomicamine-derived oxazolines—promising substrates in the synthesis of alkyl methyl sulfoxides
  作者：Danuta Brózda、Agata Głuszyńska、Agnieszka Kościołowicz、Maria D. Rozwadowska

  DOI：10.1016/j.tetasy.2005.01.027

  日期：2005.3

  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.
• Enantioselective modification of the Pomeranz–Fritsch–Bobbitt synthesis of tetrahydroisoquinoline alkaloids synthesis of (−)-salsolidine and (−)-carnegine
  作者：Agata Głuszyńska、Maria D Rozwadowska

  DOI：10.1016/s0957-4166(00)00196-8

  日期：2000.6

  (-)-Salsolidine 7 and (-)-carnegine 8 were prepared in 46 and 36% e.e., respectively, by enantioselective addition of methyllithium to the Pomeranz-Fritsch imine 13 in the presence of ligands 9 12, followed by acid-catalyzed cyclization and hydrogenolysis. (C) 2000 Elsevier Science Ltd, All rights reserved.

  (-)-Salsolidine 7 和 (-)-carnegine 8 分别以 46% 和 36% 的对映体过量百分比（e.e.）制备而成。该过程通过在配体 9-12 存在下，将甲基锂选择性地添加到 Pomeranz-Fritsch 亚胺 13 中，随后经酸催化的环化和氢解反应完成。© 2000 Elsevier Science Ltd，版权所有。