4-(2-chloro-anilino)-piperidine-1-carboxylic acid ethyl ester | 63260-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(2-chloro-anilino)-piperidine-1-carboxylic acid ethyl ester
• 英文别名: Ethyl 4-(2-chloroanilino)piperidine-1-carboxylate
• CAS: 63260-44-6
• 化学式: C₁₄H₁₉ClN₂O₂
• 分子量: 282.77
• InChiKey: HGHBSGQXLCWVAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-chloro-anilino)-piperidine-1-carboxylic acid ethyl ester 在 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 醋酸异丙酯 、 异丙醇 为溶剂， 反应 25.17h， 生成 4-(2,3-二氢-2-氧代-1H-苯并咪唑-1-基)哌啶-1-羧酸乙酯
  参考文献：
  名称：

  Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

  摘要：

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

  DOI：

  10.1021/ol061233j
• 作为产物：
  描述：

  邻氯苯胺 、 N-乙氧羰基-4-哌啶酮 在 三乙酰氧基硼氢化钠 、 三氟乙酸 作用下， 以 醋酸异丙酯 为溶剂， 反应 0.17h， 生成 4-(2-chloro-anilino)-piperidine-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

  摘要：

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

  DOI：

  10.1021/ol061233j

文献信息

• Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization
  作者：Mark McLaughlin、Michael Palucki、Ian W. Davies

  DOI：10.1021/ol061233j

  日期：2006.7.1

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.