(+)-(S)-1-(2,3-epoxypropyl)-6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine | 944152-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (+)-(S)-1-(2,3-epoxypropyl)-6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine
• 英文别名: 6,7-dimethyl-1-[[(2S)-oxiran-2-yl]methyl]-3,4-dihydro-2H-1,5-naphthyridine
• CAS: 944152-94-7
• 化学式: C₁₃H₁₈N₂O
• 分子量: 218.299
• InChiKey: MNZWWQBRUZBQOV-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(S)-1-(2,3-epoxypropyl)-6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine 、 6-(4-bromophenyl)-1,2,3,4-tetrahydro-1,5-naphthyridine 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 (2R)-1-[6-(4-bromophenyl)-3,4-dihydro-2H-1,5-naphthyridin-1-yl]-3-(6,7-dimethyl-3,4-dihydro-2H-1,5-naphthyridin-1-yl)propan-2-ol
  参考文献：
  名称：

  1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: exploration of suitable chemistry for library development

  摘要：

  The chemistry of 1,2,3,4-tetrahydro-1,5-naphthyridines and 2,3,4,5-tetrahydro-1H-pyrido[3,2-b] azepines has been explored with the goal of discovering reactions at N1 suitable for library development. Epoxide openings, Pd-catalyzed N-arylations, DEPBT-promoted acylations, and urea formation through the reaction with isocyanates were all successful. The epoxide opening chemistry using homochiral epichlorohydrin followed by epoxide reclosure and a second nucleophilic opening led to the preparation of a small 24-membered library. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.003
• 作为产物：
  描述：

  (-)-(S)-1-(3-chloro-2-hydroxypropyl)-6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到(+)-(S)-1-(2,3-epoxypropyl)-6,7-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine
  参考文献：
  名称：

  1,2,3,4-Tetrahydro-1,5-naphthyridines and related heterocyclic scaffolds: exploration of suitable chemistry for library development

  摘要：

  The chemistry of 1,2,3,4-tetrahydro-1,5-naphthyridines and 2,3,4,5-tetrahydro-1H-pyrido[3,2-b] azepines has been explored with the goal of discovering reactions at N1 suitable for library development. Epoxide openings, Pd-catalyzed N-arylations, DEPBT-promoted acylations, and urea formation through the reaction with isocyanates were all successful. The epoxide opening chemistry using homochiral epichlorohydrin followed by epoxide reclosure and a second nucleophilic opening led to the preparation of a small 24-membered library. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.04.003