(S)-5-(pyrrolidonocarbonyl)-4,5-dihydro-2-(2'-(diphenylphosphinothioyl)ethyl)-1,3-oxazole | 216862-85-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-5-(pyrrolidonocarbonyl)-4,5-dihydro-2-(2'-(diphenylphosphinothioyl)ethyl)-1,3-oxazole
• 英文别名: [(4S)-2-(2-diphenylphosphinothioylethyl)-4,5-dihydro-1,3-oxazol-4-yl]-pyrrolidin-1-ylmethanone
• CAS: 216862-85-0
• 化学式: C₂₂H₂₅N₂O₂PS
• 分子量: 412.492
• InChiKey: VOOJWRRYYRLLOS-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  74
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-(pyrrolidonocarbonyl)-4,5-dihydro-2-(2'-(diphenylphosphinothioyl)ethyl)-1,3-oxazole 在 镍 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以80%的产率得到[(S)-2-(2-Diphenylphosphanyl-ethyl)-4,5-dihydro-oxazol-4-yl]-pyrrolidin-1-yl-methanone
  参考文献：
  名称：

  Synthesis of Phosphino Oxazoline Ligand Libraries from Amino Acid and Phosphino Carboxylate Building Blocks

  摘要：

  A modular route to new phosphine-oxazoline ligands is reported. The ability of these ligands to asymmetrically catalyze the addition of dimethyl malonate to 1,3-diphenylprop-2-enyl acetate was investigated. The best of these Ligands gave a palladium complex which catalyzed the addition of dimethyl malonate to 1,3-diphenylprop-2-enyl acetate in a 99% yield and in 98% enantiomeric excess (Table 3, entry 11).

  DOI：

  10.1021/jo981420y
• 作为产物：
  描述：

  (S)-N-(tert-butoxycarbonyl)-2-hydroxyl-1-(pyrrolidinocarbonyl)ethylamine 在 伯吉斯试剂 、 四丁基氟化铵 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 131.0h， 生成 (S)-5-(pyrrolidonocarbonyl)-4,5-dihydro-2-(2'-(diphenylphosphinothioyl)ethyl)-1,3-oxazole
  参考文献：
  名称：

  Synthesis of Phosphino Oxazoline Ligand Libraries from Amino Acid and Phosphino Carboxylate Building Blocks

  摘要：

  A modular route to new phosphine-oxazoline ligands is reported. The ability of these ligands to asymmetrically catalyze the addition of dimethyl malonate to 1,3-diphenylprop-2-enyl acetate was investigated. The best of these Ligands gave a palladium complex which catalyzed the addition of dimethyl malonate to 1,3-diphenylprop-2-enyl acetate in a 99% yield and in 98% enantiomeric excess (Table 3, entry 11).

  DOI：

  10.1021/jo981420y

文献信息

• Synthesis of Phosphino Oxazoline Ligand Libraries from Amino Acid and Phosphino Carboxylate Building Blocks
  作者：Scott R. Gilbertson、Cheng-Wei T. Chang

  DOI：10.1021/jo981420y

  日期：1998.11.1

  A modular route to new phosphine-oxazoline ligands is reported. The ability of these ligands to asymmetrically catalyze the addition of dimethyl malonate to 1,3-diphenylprop-2-enyl acetate was investigated. The best of these Ligands gave a palladium complex which catalyzed the addition of dimethyl malonate to 1,3-diphenylprop-2-enyl acetate in a 99% yield and in 98% enantiomeric excess (Table 3, entry 11).