dipiperidinomethyl-2 pyridine | 35558-36-2

• 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: dipiperidinomethyl-2 pyridine
• 英文别名: di-piperidin-1-yl-pyridin-2-yl-methane；2-[di(piperidin-1-yl)methyl]pyridine
• CAS: 35558-36-2
• 化学式: C₁₆H₂₅N₃
• 分子量: 259.395
• InChiKey: COUXEXIDEXMHBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  19.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  dipiperidinomethyl-2 pyridine 、 (1-methoxy-2-phenylvinyloxy)trimethylsilane 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 以70%的产率得到piperidino-3 phenyl-2 (pyridyl-2)-3 propionate de methyle
  参考文献：
  名称：

  Aube, Philippe; Christot, Isabelle; Combret, Jean-Claude, Bulletin de la Societe Chimique de France, 1988, # 6, p. 1009 - 1014

  摘要：

  DOI：
• 作为产物：
  描述：

  在 甲烷磺酸 作用下， 以 氘代乙腈 为溶剂， 反应 48.0h， 生成 dipiperidinomethyl-2 pyridine
  参考文献：
  名称：

  Reactivity-Based Dynamic Covalent Chemistry: Reversible Binding and Chirality Discrimination of Monoalcohols

  摘要：

  In an effort to develop reactivity-based dynamic covalent bonding and to expand the scope and application of the dynamic covalent chemistry, in situ-generated simple generic iminium ions were utilized for the dynamic covalent binding of monoalcohols with high affinity. Hammett analysis was conducted to manipulate the equilibrium and correlate with the reactivity of reactants. The structural features of aldehydes and secondary amines were identified, and both polar and steric effects have significant impact on the binding. In particular, the substrates which can participate in pi-pi and polar-pi interactions are able to afford apparent equilibrium constants in the magnitude of 104 M-2, demonstrating the power of weak supramolecular forces to stabilize the dynamic covalent assembly. The generality of the assembly was validated with a series of mono secondary alcohols. To showcase the practicality of our system, chirality discrimination and ee measurement of chiral secondary alcohols were achieved.

  DOI：

  10.1021/jo502801g

文献信息

• Quantitative Reactivity Scales for Dynamic Covalent and Systems Chemistry
  作者：Yuntao Zhou、Lijie Li、Hebo Ye、Ling Zhang、Lei You

  DOI：10.1021/jacs.5b11361

  日期：2016.1.13

  induced by both EDGs and EWGs emerged in Hammett plot when cyclic secondary amines were used. This is the first time such a behavior is observed in a thermodynamically controlled system, to the best of our knowledge. Unified quantitative reactivity scales were proposed for DCC and defined by the correlation log K = S(N) (R(N) + R(E)). Nucleophilicity parameters (R(N) and S(N)) and electrophilicity parameters

  动态共价化学 (DCC) 已成为在化学和材料科学中创建分子组装和复杂系统的有力工具。在此，我们首次开发了能够关联和预测动态共价反应 (DCR) 平衡的定量反应性量表。参考反应基于亚胺（DCC 中最常用的结构基序之一）和一系列 O-、N- 和 S- 单亲核试剂之间的通用 DCR。衍生自 pyridine-2-carboxyaldehyde 的芳香族亚胺表现出通过不同的取代基效应控制平衡的能力。供电子基团 (EDGs) 通过醌式共振稳定亚胺，而吸电子基团 (EWGs) 通过增强分子内氢键稳定加合物，导致哈米特分析中的曲率。值得注意的是，当使用环状仲胺时，由 EDG 和 EWG 引起的独特非线性出现在哈米特图中。据我们所知，这是第一次在热力学控制系统中观察到这种行为。为 DCC 提出了统一的定量反应性量表，并由相关日志 K = S(N) (R(N) + R(E)) 定义。然后根据发现的 DCR 开发出亲核性参数（R(N)