methyl (4S)-2-[2-[2-[(4S)-4-methoxycarbonyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]phenyl]-4,5-dihydro-1,3-oxazole-4-carboxylate | 767356-32-1

• 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: methyl (4S)-2-[2-[2-[(4S)-4-methoxycarbonyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]phenyl]-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 767356-32-1
• 化学式: C₂₂H₂₀N₂O₆
• 分子量: 408.411
• InChiKey: DKXIQMVCNSLXJW-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (4S)-2-[2-[2-[(4S)-4-methoxycarbonyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]phenyl]-4,5-dihydro-1,3-oxazole-4-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到2,2'-bis[(4'R)-(hydroxymethyl)oxazolin-2'-yl]-1,1'-biphenyl
  参考文献：
  名称：

  Bisoxazoline ligands with an axial-unfixed biaryl backbone: the effects of the biaryl backbone and the substituent at oxazoline ring on Cu-catalyzed asymmetric cyclopropanation

  摘要：

  The synthesis of novel C-symmetric bisoxazoline ligands with an axial-unfixed biaryl backbone and different substituents at the oxazoline ring is reported. The diastcreomer equilibrium of these ligands in solution and their complexation behavior with the copper(I) ion were Studied. Their application in Cu-catalyzed cyclopropanation of styrene, with diazoacetate, was carried out and the effects of the biaryl backbone and the substituent on the oxazoline ring in the catalysis were examined. The best result was obtained with the ligand having a 1,1'-binaphthyl backbone and a t-butyl group on the oxazoline ring, which afforded 89% de and 96% de for the trans- and cis-products of the above asymmetric cyclopropanation reaction, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.014
• 作为产物：
  描述：

  2,2'-biphenyldicarboxylic acid dichloride 在 methoxycarbonylsulfamoyl-triethylammmonium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 methyl (4S)-2-[2-[2-[(4S)-4-methoxycarbonyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl]phenyl]-4,5-dihydro-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  Bisoxazoline ligands with an axial-unfixed biaryl backbone: the effects of the biaryl backbone and the substituent at oxazoline ring on Cu-catalyzed asymmetric cyclopropanation

  摘要：

  The synthesis of novel C-symmetric bisoxazoline ligands with an axial-unfixed biaryl backbone and different substituents at the oxazoline ring is reported. The diastcreomer equilibrium of these ligands in solution and their complexation behavior with the copper(I) ion were Studied. Their application in Cu-catalyzed cyclopropanation of styrene, with diazoacetate, was carried out and the effects of the biaryl backbone and the substituent on the oxazoline ring in the catalysis were examined. The best result was obtained with the ligand having a 1,1'-binaphthyl backbone and a t-butyl group on the oxazoline ring, which afforded 89% de and 96% de for the trans- and cis-products of the above asymmetric cyclopropanation reaction, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.014