methyl 2'-(4-methoxyphenyl)-1-benzyl-2-oxo-4'H-spiro[indoline-3,5'-oxazole]-4'-cis-carboxylate

• 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 2'-(4-methoxyphenyl)-1-benzyl-2-oxo-4'H-spiro[indoline-3,5'-oxazole]-4'-cis-carboxylate
• 英文别名: methyl (4R,5S)-1'-benzyl-2-(4-methoxyphenyl)-2'-oxospiro[4H-1,3-oxazole-5,3'-indole]-4-carboxylate
• 化学式: C₂₆H₂₂N₂O₅
• 分子量: 442.471
• InChiKey: ARNMTNVRGTVIPV-NVQXNPDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(4-methoxybenzoyl)glycine methyl ester 在 碘 、 四氯化钛 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 methyl 2'-(4-methoxyphenyl)-1-benzyl-2-oxo-4'H-spiro[indoline-3,5'-oxazole]-4'-cis-carboxylate 、 methyl 2'-(4-methoxyphenyl)-1-benzyl-2-oxo-4'H-spiro[indoline-3,5'-oxazole]-4'-carboxylate
  参考文献：
  名称：

  Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines

  摘要：

  A regio- and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >99:1). Substitution at the 4-position of the oxazole controls nucleophilic attack to provide either the 2-oxazoline or 3-oxazoline spirocycle with excellent (>99:1) regiocontrol.

  DOI：

  10.1021/ol1027305

文献信息

• Titanium-Catalyzed Stereoselective Synthesis of Spirooxindole Oxazolines
  作者：Joseph J. Badillo、Gary E. Arevalo、James C. Fettinger、Annaliese K. Franz

  DOI：10.1021/ol1027305

  日期：2011.2.4

  A regio- and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium(IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >99:1). Substitution at the 4-position of the oxazole controls nucleophilic attack to provide either the 2-oxazoline or 3-oxazoline spirocycle with excellent (>99:1) regiocontrol.