(4S,5S,R_S)-4-methoxymethyl-5-(4-methylsulfinylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazole | 850449-37-5

• 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,R_S)-4-methoxymethyl-5-(4-methylsulfinylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazole
• 英文别名: (4S,5S)-4-(methoxymethyl)-5-[4-[(R)-methylsulfinyl]phenyl]-2-phenyl-4,5-dihydro-1,3-oxazole
• CAS: 850449-37-5
• 化学式: C₁₈H₁₉NO₃S
• 分子量: 329.42
• InChiKey: GYKPTTOSBRWEBJ-HKARXFIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 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：
  67.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叔丁基锂 、 (4S,5S,R_S)-4-methoxymethyl-5-(4-methylsulfinylphenyl)-2-phenyl-4,5-dihydro-1,3-oxazole 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.5h， 以47%的产率得到(S)-tert-butyl methyl sulfoxide
  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)-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

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.