N-boc-4-(2-氯吡啶-3-基)哌啶-4-甲酰胺 | 1315335-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: N-boc-4-(2-氯吡啶-3-基)哌啶-4-甲酰胺
• 英文名称: N-Boc-4-(2-chloropyridin-3-yl)piperidine-4-carboxamide
• 英文别名: 1-Piperidinecarboxylic acid, 4-(aminocarbonyl)-4-(2-chloro-3-pyridinyl)-, 1,1-dimethylethyl ester；tert-butyl 4-carbamoyl-4-(2-chloropyridin-3-yl)piperidine-1-carboxylate
• CAS: 1315335-15-9
• 化学式: C₁₆H₂₂ClN₃O₃
• 分子量: 339.822
• InChiKey: OAQLRPOHHHVURF-UHFFFAOYSA-N

物化性质

• 沸点：
  524.6±50.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-boc-4-(2-氯吡啶-3-基)哌啶-4-甲酰胺 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以3.48 g的产率得到2'-氧代-1',2'-二氢螺[哌啶-4,3'-吡咯并[2,3-B]吡啶]-1-羧酸叔丁酯
  参考文献：
  名称：

  A spirocyclic oxindole analogue: Synthesis and antitumor activities

  摘要：

  A new synthesis of spirocyclic oxindole analogue spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 1 is described. The key steps involve dialkylation of arylacetonitrile and cyclization of the azaoxindole ring by an intramolecular Buchwald Hartwig amidation of carboxylic amide and aryl chloride. A small library was obtained by reductive amination of 1 with various aldehydes and was screened against human lung cancer cell A549, human liver cancer cell BEL7402, and human colon cancer cell HCT-8. The results show that most of the library compounds 2 have some inhibitory activities. 2-(Trifluoromethoxy) benzylic substituted spirocyclic azaoxindole 2e was identified as a nanomolar inhibitor against human lung cancer cell A-549 (IC50 = 50 nmol/L). (C) 2011 Da Wei Teng. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.01.042
• 作为产物：
  描述：

  2-氯-3-吡啶甲醇 在 磺酰氯 、 双氧水 、 sodium hydride 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 N-boc-4-(2-氯吡啶-3-基)哌啶-4-甲酰胺
  参考文献：
  名称：

  A spirocyclic oxindole analogue: Synthesis and antitumor activities

  摘要：

  A new synthesis of spirocyclic oxindole analogue spiro[piperidine-4,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one 1 is described. The key steps involve dialkylation of arylacetonitrile and cyclization of the azaoxindole ring by an intramolecular Buchwald Hartwig amidation of carboxylic amide and aryl chloride. A small library was obtained by reductive amination of 1 with various aldehydes and was screened against human lung cancer cell A549, human liver cancer cell BEL7402, and human colon cancer cell HCT-8. The results show that most of the library compounds 2 have some inhibitory activities. 2-(Trifluoromethoxy) benzylic substituted spirocyclic azaoxindole 2e was identified as a nanomolar inhibitor against human lung cancer cell A-549 (IC50 = 50 nmol/L). (C) 2011 Da Wei Teng. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.01.042