2,6-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine | 1584222-73-0

• 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: 2,6-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine
• 英文别名: 2,6-Dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine
• CAS: 1584222-73-0
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: LSZKFWLMKLXXSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 chloropyridinecobaloxime(III) 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以90%的产率得到2,6-dimethyl-1,5-naphthyridine
  参考文献：
  名称：

  通过合并可见光光氧化还原催化和钴催化对N-杂环进行无受体脱氢

  摘要：

  本文描述了四氢喹啉（THQs），二氢吲哚和其他相关的N-杂环在环境温度下的首次无受体脱氢，方法是合并可见光光氧化还原催化和钴催化。演示了在有机转化和储氢材料中的潜在应用。初步的机械研究表明，催化循环主要通过氧化淬灭途径发生。

  DOI：

  10.1002/anie.201612486
• 作为产物：
  描述：

  2,6-dimethyl-1,5-naphthyridine 在 C₂₂H₂₃IrN₂O₃ 、 [(η5-pentamethylcyclopentadienyl)Ir(2,2'-bipyridine-6,6'-dionato)(PhNH2)] 、 氢气 作用下， 以 对二甲苯 为溶剂， 110.0 ℃ 、7.09 MPa 条件下， 反应 68.0h， 生成 2,6-dimethyl-1,2,3,4-tetrahydro-1,5-naphthyridine
  参考文献：
  名称：

  Homogeneous Perdehydrogenation and Perhydrogenation of Fused Bicyclic N-Heterocycles Catalyzed by Iridium Complexes Bearing a Functional Bipyridonate Ligand

  摘要：

  Homogeneous perdehydrogenation of saturated bicyclic 2,6-dimethyldecahydro-1,5-naphthyridine and perhydrogenation of aromatic 2,6-dimethyl-1,5-naphthyridine with release and uptake of five molecules of H-2 are efficiently achieved by iridium complexes bearing a functional bipyridonate ligand. Successive perhydrogenation and perdehydrogenation of 2,6-dimethyl-1,5-naphthryridine using a single iridium complex also proceed with the reversible inter-conversion of the catalytic species, depending on the presence or absence of H-2.

  DOI：

  10.1021/ja5001888

文献信息

• Asymmetric Ruthenium-Catalyzed Hydrogenation of 2,6-Disubstituted 1,5-Naphthyridines: Access to Chiral 1,5-Diaza-<i>cis</i>-Decalins
  作者：Jianwei Zhang、Fei Chen、Yan-Mei He、Qing-Hua Fan

  DOI：10.1002/anie.201411105

  日期：2015.4.7

  developed. A wide range of 1,5‐naphthyridine derivatives were efficiently hydrogenated to give 1,2,3,4‐tetrahydro‐1,5‐naphthyridines with up to 99 % ee and full conversions. This facile and green protocol is applicable to the scaled‐up synthesis of optically pure 1,5‐diaza‐cis‐decalins, which have been used as rigid chelating diamine ligands for asymmetric synthesis.

  已经开发了由手性阳离子钌二胺络合物催化的2,6-二取代和2,3,6-三取代的1,5-萘啶的不对称氢化（AH）。各种1,5-萘啶衍生物均被有效氢化，得到1,2,3,4-四氢-1,5-萘啶类化合物，ee最高可达99％， 并且可以完全转化。该简便而绿色的方案适用于光学纯的1,5-二氮杂顺式十氢化萘的放大合成，该合成已用作不对称合成的刚性螯合二胺配体。
• Acceptorless Dehydrogenation of N-Heterocycles by Merging Visible-Light Photoredox Catalysis and Cobalt Catalysis
  作者：Ke-Han He、Fang-Fang Tan、Chao-Zheng Zhou、Gui-Jiang Zhou、Xiao-Long Yang、Yang Li

  DOI：10.1002/anie.201612486

  日期：2017.3.6

  Herein, the first acceptorless dehydrogenation of tetrahydroquinolines (THQs), indolines, and other related N‐heterocycles, by merging visible‐light photoredox catalysis and cobalt catalysis at ambient temperature, is described. The potential applications to organic transformations and hydrogen‐storage materials are demonstrated. Primary mechanistic investigations indicate that the catalytic cycle

  本文描述了四氢喹啉（THQs），二氢吲哚和其他相关的N-杂环在环境温度下的首次无受体脱氢，方法是合并可见光光氧化还原催化和钴催化。演示了在有机转化和储氢材料中的潜在应用。初步的机械研究表明，催化循环主要通过氧化淬灭途径发生。
• Homogeneous Perdehydrogenation and Perhydrogenation of Fused Bicyclic N-Heterocycles Catalyzed by Iridium Complexes Bearing a Functional Bipyridonate Ligand
  作者：Ken-ichi Fujita、Yui Tanaka、Masato Kobayashi、Ryohei Yamaguchi

  DOI：10.1021/ja5001888

  日期：2014.4.2

  Homogeneous perdehydrogenation of saturated bicyclic 2,6-dimethyldecahydro-1,5-naphthyridine and perhydrogenation of aromatic 2,6-dimethyl-1,5-naphthyridine with release and uptake of five molecules of H-2 are efficiently achieved by iridium complexes bearing a functional bipyridonate ligand. Successive perhydrogenation and perdehydrogenation of 2,6-dimethyl-1,5-naphthryridine using a single iridium complex also proceed with the reversible inter-conversion of the catalytic species, depending on the presence or absence of H-2.