(2S,4S,5R)-[4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-phenyl-methanone | 166189-33-9

• 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: (2S,4S,5R)-[4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-phenyl-methanone
• CAS: 166189-33-9
• 化学式: C₂₄H₂₃NO₄S
• 分子量: 421.517
• InChiKey: REFIFNMRVDSWCQ-NWVWQQAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,4S,5R)-[4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-phenyl-methanone 在 18-冠醚-6 、 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1R,2'S,4'S,5'R)-[4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl]-phenyl-methanol 、 (1S,2'S,4'S,5'R)-[4'-methyl-5'-phenyl-3'-(toluene-4''-sulfonyl)-oxazolidin-2'-yl]-phenyl-methanol
  参考文献：
  名称：

  Diastereoselective addition of metal-coordinated and “naked” nucleophilic reagents to norephedrine derived 2-acyl-N-tosyl-oxazolidines

  摘要：

  The addition of tri-s-butyl borohydrides to the 2-acetyl-1,3-oxazolidine 1 could be directed with high selectivity to either the Si or the Re pi-carbonyl face under chelating or non-coordinating conditions respectively. Addition of hydrides to the corresponding phenyl ketone 2 was highly Si selective only in the former conditions. Grignard reagents and organolithiums add to the methyl ketone 1 with remarkable Si and Re pi-face selectivity respectively. With phenyl ketone 2 only organomagnesium reagents follow the above trend. This data are in accord with a Felkin-type or a stereochemically opposite chelaled mode of addition of these nucleophiles in the absence or in the presence of chelating metal counterions respectively. (C) 1997, Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01087-3
• 作为产物：
  描述：

  (2S,4S,5R)-4-methyl-5-phenyl-2-(1-phenyl-vinyl)-3-(toluene-4'-sulfonyl)-oxazolidine 在 sodium periodate 、 osmium (III) chloride 、 十二/十四烷基二甲基氧化胺 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (2S,4S,5R)-[4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-oxazolidin-2-yl]-phenyl-methanone
  参考文献：
  名称：

  Diastereoselective addition of metal-coordinated and “naked” nucleophilic reagents to norephedrine derived 2-acyl-N-tosyl-oxazolidines

  摘要：

  The addition of tri-s-butyl borohydrides to the 2-acetyl-1,3-oxazolidine 1 could be directed with high selectivity to either the Si or the Re pi-carbonyl face under chelating or non-coordinating conditions respectively. Addition of hydrides to the corresponding phenyl ketone 2 was highly Si selective only in the former conditions. Grignard reagents and organolithiums add to the methyl ketone 1 with remarkable Si and Re pi-face selectivity respectively. With phenyl ketone 2 only organomagnesium reagents follow the above trend. This data are in accord with a Felkin-type or a stereochemically opposite chelaled mode of addition of these nucleophiles in the absence or in the presence of chelating metal counterions respectively. (C) 1997, Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01087-3