2-chloro-2-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-1-phenylethanol | 1028306-32-2

• 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: 2-chloro-2-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-1-phenylethanol
• CAS: 1028306-32-2
• 化学式: C₁₉H₂₀ClNO₃
• 分子量: 345.826
• InChiKey: XLGIMJIZOBAOKF-BFWZDYSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-2-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-1-phenylethanol 在 sodium hydroxide 、 水 作用下， 以 异丙醇 为溶剂， 生成 (1S,2S,4'S,5'S)-cis-1,2-epoxy-1-(4-methoxymethyl-5-phenyl-2-oxazolin-2-yl)-2-phenylethane 、 (1S,2R,4'S,5'S)-trans-1,2-epoxy-1-(4-methoxymethyl-5-phenyl-2-oxazolin-2-yl)-2-phenylethane 、 (1R,2S,4'S,5'S)-trans-1,2-epoxy-1-(4-methoxymethyl-5-phenyl-2-oxazolin-2-yl)-2-phenylethane 、 (1R,2R,4'S,5'S)-cis-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
• 作为产物：
  描述：

  (4S,5S)-2-chloromethyl-4-methoxymethyl-5-phenyl-2-oxazoline 在 二乙基异丙基胺 作用下， 以 乙醚 为溶剂， 生成 2-chloro-2-[(4S,5S)-4-(methoxymethyl)-5-phenyl-4,5-dihydro-1,3-oxazol-2-yl]-1-phenylethanol
  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