2-cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic acid methyl ester | 144688-88-0

• 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-cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic acid methyl ester
• 英文别名: Methyl 6-cyano-3,4-dihydropyridine-1(2H)-carboxylate；methyl 6-cyano-3,4-dihydro-2H-pyridine-1-carboxylate
• CAS: 144688-88-0
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: UDJKRWUAGPIVAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic acid methyl ester 在 四乙基对甲苯磺酸铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 methyl 6-ethyl-3,6-dihydro-2H-pyridine-1-carboxylate
  参考文献：
  名称：

  有机化学139.腈的电还原脱氰及其在α-烷基胺合成中的应用

  摘要：

  当在含有Et 4 NOTs作为支持电解质的非质子传递溶剂（DMF或MeCN）中将Zn用作阴极材料时，腈的电还原得到相应的脱氰产物。通过使胺在α位氰化，然后将所得的α-氨基腈进行α-烷基化，然后进行电还原脱氰作用，可以有效地实现α-位胺的烷基化。

  DOI：

  10.1016/s0040-4020(01)80493-2
• 作为产物：
  描述：

  甲基3,4-二氢-1(2H)-吡啶羧酸酯 在 溴 、 四氯化钛 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 2-cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic acid methyl ester
  参考文献：
  名称：

  Reactivity of 2-cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic acid esters towards various nucleophiles: Regio- and stereoselectivity of the attack

  摘要：

  The synthesis and reactivity of the title compounds towards nucleophiles are discussed. The regio-and diastereoselectivity of the attack is highly dependent on the carbamic ester and the type of nucleophile applied. Both Michael type addition across the activated double bond and S(N)2T reaction at the carbamate carbon atom were observed. Structure assignment of the adducts in solution and in the solid state was performed utilizing high temperature NMR techniques as well as single crystal X-ray diffraction.

  DOI：

  10.1007/bf00806971

文献信息

• Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
  作者：Tatsuya Shono、Jun Terauchi、Kenji Kitayama、Yo-ichiro Takeshima、Yoshihiro Masumura

  DOI：10.1016/s0040-4020(01)80493-2

  日期：——

  Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.

  当在含有Et 4 NOTs作为支持电解质的非质子传递溶剂（DMF或MeCN）中将Zn用作阴极材料时，腈的电还原得到相应的脱氰产物。通过使胺在α位氰化，然后将所得的α-氨基腈进行α-烷基化，然后进行电还原脱氰作用，可以有效地实现α-位胺的烷基化。
• Reactivity of 2-cyano-1,4,5,6-tetrahydro-1-pyridinecarboxylic acid esters towards various nucleophiles: Regio- and stereoselectivity of the attack
  作者：P. Stanetty、M. D. Mihovilovic、K. Mereiter

  DOI：10.1007/bf00806971

  日期：1997.10

  The synthesis and reactivity of the title compounds towards nucleophiles are discussed. The regio-and diastereoselectivity of the attack is highly dependent on the carbamic ester and the type of nucleophile applied. Both Michael type addition across the activated double bond and S(N)2T reaction at the carbamate carbon atom were observed. Structure assignment of the adducts in solution and in the solid state was performed utilizing high temperature NMR techniques as well as single crystal X-ray diffraction.