N-(2-甲基环己基)吡啶酰胺 | 1008993-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: N-(2-甲基环己基)吡啶酰胺
• 英文名称: N-(2-methylcyclohexyl) picolinamide
• 英文别名: N-(2-methylcyclohexyl)pyridine-2-carboxamide
• CAS: 1008993-11-0
• 化学式: C₁₃H₁₈N₂O
• mdl: MFCD11727160
• 分子量: 218.299
• InChiKey: DJHZNCXSQOFNIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.538
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 N-(2-甲基环己基)吡啶酰胺 在 2,2,6,6-四甲基哌啶氧化物 、 palladium diacetate 作用下， 120.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以78%的产率得到
  参考文献：
  名称：

  Pd-Catalyzed C(sp³)–H Carbonylation of Alkylamines: A Powerful Route to γ-Lactams and γ-Amino Acids

  摘要：

  A novel Pd-catalyzed direct C(sp(3))-H carbonylation of alkylamines for the synthesis of gamma-lactams and gamma-amino acids has been developed, in which TEMPO was used as the crucial sole oxidant. The synthetic prospect was demonstrated by the concise total synthesis of rac-Pregbalin.

  DOI：

  10.1021/acs.orglett.5b01658
• 作为产物：
  描述：

  2-甲基环己胺 、 苯甲酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到N-(2-甲基环己基)吡啶酰胺
  参考文献：
  名称：

  Pd-Catalyzed C(sp³)–H Carbonylation of Alkylamines: A Powerful Route to γ-Lactams and γ-Amino Acids

  摘要：

  A novel Pd-catalyzed direct C(sp(3))-H carbonylation of alkylamines for the synthesis of gamma-lactams and gamma-amino acids has been developed, in which TEMPO was used as the crucial sole oxidant. The synthetic prospect was demonstrated by the concise total synthesis of rac-Pregbalin.

  DOI：

  10.1021/acs.orglett.5b01658

文献信息

• Palladium catalyzed acetoxylation of benzylic C–H bonds using a bidentate picolinamide directing group
  作者：Tao Cheng、Weiyu Yin、Yi Zhang、Yingnan Zhang、Yong Huang

  DOI：10.1039/c3ob42196a

  日期：——

  A general palladium catalyzed acetoxylation of benzylic C–H bonds has been developed. Picolinamides serve as an excellent directing group for the C–H activation of benzylic methyls. A wide range of 2-amino benzyl alcohol analogues were synthesized in good yields. The products demonstrated broad synthetic utilities toward various benzo-fused heterocycles. Mechanistic studies revealed the key rate-limiting

  已经开发出了一般的钯催化的苄基CH键的乙酰氧基化反应。吡啶甲酰胺是苄基甲基C–H活化的极好指导基团。以高产率合成了多种2-氨基苄醇类似物。该产品对各种苯并稠合杂环具有广泛的合成用途。机理研究表明，关键的限速C–H插入步骤可能受母体芳烃取代模式的影响。
• Pd-Catalyzed C(sp³)–H Carbonylation of Alkylamines: A Powerful Route to γ-Lactams and γ-Amino Acids
  作者：Pei-Long Wang、Yan Li、Yun Wu、Chao Li、Quan Lan、Xi-Sheng Wang

  DOI：10.1021/acs.orglett.5b01658

  日期：2015.8.7

  A novel Pd-catalyzed direct C(sp(3))-H carbonylation of alkylamines for the synthesis of gamma-lactams and gamma-amino acids has been developed, in which TEMPO was used as the crucial sole oxidant. The synthetic prospect was demonstrated by the concise total synthesis of rac-Pregbalin.