5-tert-Butoxycarbonylamino-8-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester | 887945-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-tert-Butoxycarbonylamino-8-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester
• CAS: 887945-75-7
• 化学式: C₂₂H₂₄N₂O₅
• 分子量: 396.443
• InChiKey: CVLLTNUFBUDAHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-tert-Butoxycarbonylamino-8-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester 在 sodium acetate 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 5-(Carboxymethyl-amino)-8-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester
  参考文献：
  名称：

  Synthesis of Indoles via 6π-Electrocyclic Ring Closures of Trienecarbamates

  摘要：

  A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 degrees C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.

  DOI：

  10.1021/ja060282o
• 作为产物：
  描述：

  5-tert-Butoxycarbonylamino-8-methyl-4-oxo-3,4,8,8a-tetrahydro-2H-quinoline-1-carboxylic acid phenyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以93.1 mg的产率得到5-tert-Butoxycarbonylamino-8-methyl-4-oxo-3,4-dihydro-2H-quinoline-1-carboxylic acid phenyl ester
  参考文献：
  名称：

  Synthesis of Indoles via 6π-Electrocyclic Ring Closures of Trienecarbamates

  摘要：

  A new method for the preparation of indoles from readily available alpha-haloenones and alpha-(trialkylstannyl)enecarbamates is described. Following a Stille coupling, trienecarbamate 2 is electronically activated to undergo a facile 6pi-electrocyclic ring closure and subsequent oxidation to afford protected aniline 4. Upon deprotection and reductive amination, acid 5 underwent clean cyclization to N-acetylindole 6 (Ac2O, NEt3, 130 degrees C). This method has been used to construct a variety of substituted indoles that are not easily prepared by conventional indole annelation methods.

  DOI：

  10.1021/ja060282o