2,5-dihydropyridine | 67684-02-0

• 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
• 英文名称: 2,5-dihydropyridine
• 英文别名: 3,6-dihydropyridine
• CAS: 67684-02-0
• 化学式: C₅H₇N
• 分子量: 81.1173
• InChiKey: LPHWCAUEPAUFHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吡啶 在 lithium aluminium tetrahydride 、 水 作用下， 生成 1,4-二氢吡啶 、 1,2-二氢吡啶 、 2,5-dihydropyridine
  参考文献：
  名称：

  On the structure and mechanism of formation of the Lansbury reagent, lithium tetrakis(N-dihydropyridyl)aluminate

  摘要：

  The reaction of lithium aluminum hydride (LAH) and pyridine yields five lithium tetrakis(N-dihydropyridyl)aluminate (LDPA) isomers. The LDPA isomers are formed reversibly and contain both 1,2- and 1,4-dihydropyridyl ligands. The 1,2-dihydropyridyl ligands are incorporated as the products of kinetic control while the 1,4-dihydropyridyl ligands are formed as the thermodynamic products. When LDPA is synthesized using lithium aluminum deuteride and the deuterated LDPA is placed in pyridine solvent, the ligands exchange with the pyridine in the solvent pool and form pyridine which is deuterated mainly in the 2- and 4-positions. A small amount of 3-deuterated pyridine is also detected. The formation of 3-deuteriopyridine suggests that the pyridine radical anion is an intermediate present during the reaction of LAH with pyridine. In support of this suggestion, when LAH and pyridine are mixed, the EPR spectrum of the lithium salt of the pyridyl radical anion is observed. The stepwise addition of ligands to form LDPA is observed (NMR). Five aluminate species are detectable (Al-27 NMR): LAH, mono-, di-, and trisubstituted aluminum hydride, and LDPA. The hydrolysis of LDPA in solvent pyridine-d5 yields a mixture of 1,4-, 1,2-, and 2,5-dihydropyridines. The dihydropyridines are stable in the absence of oxygen.

  DOI：

  10.1021/jo00059a041

文献信息

• Evaluation of Organic Hydride Donors as Reagents for the Reduction of Carbon Dioxide and Metal-Bound Formates
  作者：Timothy E. Elton、Graham E. Ball、Mohan Bhadbhade、Leslie D. Field、Stephen B. Colbran

  DOI：10.1021/acs.organomet.8b00600

  日期：2018.11.12

  A variety of organic hydride donors (OHDs) have been tested as reagents for the transfer of hydride to iron formato complexes in the activation and reduction of carbon dioxide. Theoretical calculations show that the selection of OHD and solvent is crucial when planning systems involving OHD cooperativity. Strong consideration is given to the likelihood that metal centers may deactivate formate to hydride

  已经测试了多种有机氢化物供体（OHD）作为在二氧化碳的活化和还原过程中将氢化物转移至甲酰铁络合物的试剂。理论计算表明，在计划涉及OHD合作性的系统时，选择OHD和溶剂至关重要。强烈考虑了金属中心可能使甲酸酯失活而发生氢化物侵蚀的可能性，因为通常而言，与有机甲酸酯或甲酸相比，与金属中心络合时，甲酸酯基团具有更多的共振稳定能。实验证明1，2-二氢吡啶不是有效的二氧化碳还原剂。