(1S,2R,4'S,5'S)-trans-1,2-epoxy-1-(4-methoxymethyl-5-phenyl-2-oxazolin-2-yl)-2-phenylethane | 355410-72-9

• 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: (1S,2R,4'S,5'S)-trans-1,2-epoxy-1-(4-methoxymethyl-5-phenyl-2-oxazolin-2-yl)-2-phenylethane
• 英文别名: (4S,5S)-4-(methoxymethyl)-5-phenyl-2-[(2S,3R)-3-phenyloxiran-2-yl]-4,5-dihydro-1,3-oxazole
• CAS: 355410-72-9
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: KUWVAGWDWBSPFQ-FJIDUMEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,4'S,5'S)-trans-1,2-epoxy-1-(4-methoxymethyl-5-phenyl-2-oxazolin-2-yl)-2-phenylethane 在 三氟甲烷磺酸甲酯 、 sodium tetrahydroborate 、 草酸 作用下， 生成 (2S,3R)-3-苯基环氧乙烷-2-甲醛
  参考文献：
  名称：

  Azaenolates of 2-Chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline − A Highly Diastereo- and Enantioselective Synthesis of Oxazolinyloxiranes

  摘要：

  The oxazoline-derived titanium azaenolate 6 couples highly stereoselectively with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very poor or no stereoselectivity. Lithium, aluminum and tin azaenolates have also been shortly studied.

  DOI：

  10.1002/1099-0690(200106)2001:11<2035::aid-ejoc2035>3.0.co;2-r
• 作为产物：
  描述：

  苯甲醛 、 (4S,5S)-2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline 在 titanium(IV) isopropylate 、 lithium diisopropyl amide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 0.27h， 以70%的产率得到(1S,2R,4'S,5'S)-trans-1,2-epoxy-1-(4-methoxymethyl-5-phenyl-2-oxazolin-2-yl)-2-phenylethane
  参考文献：
  名称：

  Azaenolates of 2-Chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline − A Highly Diastereo- and Enantioselective Synthesis of Oxazolinyloxiranes

  摘要：

  The oxazoline-derived titanium azaenolate 6 couples highly stereoselectively with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very poor or no stereoselectivity. Lithium, aluminum and tin azaenolates have also been shortly studied.

  DOI：

  10.1002/1099-0690(200106)2001:11<2035::aid-ejoc2035>3.0.co;2-r

文献信息

• Azaenolates of 2-Chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline − A Highly Diastereo- and Enantioselective Synthesis of Oxazolinyloxiranes
  作者：Vito Capriati、Saverio Florio、Renzo Luisi

  DOI：10.1002/1099-0690(200106)2001:11<2035::aid-ejoc2035>3.0.co;2-r

  日期：2001.6

  The oxazoline-derived titanium azaenolate 6 couples highly stereoselectively with aldehydes affording highly optically pure oxazolinyloxiranes 7. The epoxide 7a has been deblocked to form the optically pure formyl oxirane 9. In contrast, the corresponding boron azaenolates 2 and 3 couple with very poor or no stereoselectivity. Lithium, aluminum and tin azaenolates have also been shortly studied.