N-(2-bromopyridin-3-yl)formamide | 1160653-52-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-bromopyridin-3-yl)formamide
• CAS: 1160653-52-0
• 化学式: C₆H₅BrN₂O
• 分子量: 201.023
• InChiKey: MYTRCECSHFVESW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  N-(2-bromopyridin-3-yl)formamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以82%的产率得到2-bromo-3-isocyanopyridine
  参考文献：
  名称：

  Reactions of ortho-Lithiophenyl (-Hetaryl) Isocyanides with Carbonyl Compounds: Rearrangements of 2-Metalated 4H-3,1-Benzoxazines

  摘要：

  ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36-89%, nine examples), 4H-3,1-benzoxazines 9 (45-78%, six examples) or, after two types of rearrangements, isobenzofuran-1(3H)-imines (iminophthalanes) 18 (52-75%, four examples), or indolin-2-ones 19 (42-79%, two. examples), depending on the reaction conditions and substitution patterns. Isocyanoalcohols 8, in turn, were converted to 9 or 18 under Cu(I) catalysis (66-86%, eight examples). 4H-3, 1-Benzoxazin-4-ones 39-Nu and isatoic anhydride 40 were obtained by the reaction of 2 with carbon dioxide followed by trapping of the lithiated intermediate with iodine and subsequent reactions with nucleophiles (45-60%, three examples).

  DOI：

  10.1021/jo9004734
• 作为产物：
  描述：

  2-溴-3-氨基吡啶 、 甲酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 24.0h， 以91%的产率得到N-(2-bromopyridin-3-yl)formamide
  参考文献：
  名称：

  Reactions of ortho-Lithiophenyl (-Hetaryl) Isocyanides with Carbonyl Compounds: Rearrangements of 2-Metalated 4H-3,1-Benzoxazines

  摘要：

  ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36-89%, nine examples), 4H-3,1-benzoxazines 9 (45-78%, six examples) or, after two types of rearrangements, isobenzofuran-1(3H)-imines (iminophthalanes) 18 (52-75%, four examples), or indolin-2-ones 19 (42-79%, two. examples), depending on the reaction conditions and substitution patterns. Isocyanoalcohols 8, in turn, were converted to 9 or 18 under Cu(I) catalysis (66-86%, eight examples). 4H-3, 1-Benzoxazin-4-ones 39-Nu and isatoic anhydride 40 were obtained by the reaction of 2 with carbon dioxide followed by trapping of the lithiated intermediate with iodine and subsequent reactions with nucleophiles (45-60%, three examples).

  DOI：

  10.1021/jo9004734

文献信息

• HYPOGLYCEMIC AND HYPOLIPIDEMIC COMPOUNDS
  申请人：ELI LILLY AND COMPANY

  公开号：EP0925063A1

  公开（公告）日：1999-06-30
• EP0925063A4
  申请人：——

  公开号：EP0925063A4

  公开（公告）日：2000-12-27
• EP1019378A4
  申请人：——

  公开号：EP1019378A4

  公开（公告）日：2001-09-26
• US6121282A
  申请人：——

  公开号：US6121282A

  公开（公告）日：2000-09-19
• US6194446B1
  申请人：——

  公开号：US6194446B1

  公开（公告）日：2001-02-27