3-methyl-4,5-diphenyl-4,5-dihydroisoxazole | 42948-77-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-methyl-4,5-diphenyl-4,5-dihydroisoxazole
• 英文别名: 3-methyl-4,5-diphenyl-4,5-dihydro-isoxazole；3-Methyl-4,5-diphenyl-4,5-dihydro-1,2-oxazole
• CAS: 42948-77-6
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: OBSRUGSKLYAQBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-4,5-diphenyl-4,5-dihydroisoxazole 、 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-ethanesulfinate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 3-<(R_S)-ethylsulfinylmethyl>-4,5-diphenyl-4,5-dihydroisoxazole 、 3-<(R_S)-ethylsulfinylmethyl>-4,5-diphenyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  Enantioselective preparation of alkyl alkylsulfanylmethyl sulfoxides and 4,5-dihydroisoxazoles from alkanesulfinates of 1,2 : 5,6-di-O-isopropylidene-D-glucose

  摘要：

  Reaction of (R) and (S)-alkanesulfinates of 1,2:5,6-di-O-isopropylidene-D-glucose (DAG) with methylsulfanylmethyllithium produces their corresponding dithioacetal mono-S-oxides with enantiomeric excesses ranging from 95 to 100%. On the other hand, exo-metallation of 3-methyl-4,5-dihydroisoxazoles and their subsequent reaction with (R)- and (S)-alkanesulfinates of DAG produces optically active 3-ethylsulfinylmethyl-4,5-dihydroisoxazoles.

  DOI：

  10.1039/p19940002177

文献信息

• Enantioselective preparation of alkyl alkylsulfanylmethyl sulfoxides and 4,5-dihydroisoxazoles from alkanesulfinates of 1,2 : 5,6-di-O-isopropylidene-<scp>D</scp>-glucose
  作者：Yolanda Arroyo-Gómez、Juan A. López-Sastre、Justo F. Rodríguez-Amo、Mercedes Santos-García、María A. Sanz-Tejedor

  DOI：10.1039/p19940002177

  日期：——

  Reaction of (R) and (S)-alkanesulfinates of 1,2:5,6-di-O-isopropylidene-D-glucose (DAG) with methylsulfanylmethyllithium produces their corresponding dithioacetal mono-S-oxides with enantiomeric excesses ranging from 95 to 100%. On the other hand, exo-metallation of 3-methyl-4,5-dihydroisoxazoles and their subsequent reaction with (R)- and (S)-alkanesulfinates of DAG produces optically active 3-ethylsulfinylmethyl-4,5-dihydroisoxazoles.