dimethyl 3-(dimethylamino)-4-methyl-5H-cyclopenta[c]-pyridine-6,6(7H)-dicarboxylate | 1360557-09-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dimethyl 3-(dimethylamino)-4-methyl-5H-cyclopenta[c]-pyridine-6,6(7H)-dicarboxylate
• 英文别名: dimethyl 3-(dimethylamino)-4-methyl-5H-cyclopenta[c]pyridine-6,6(7H)-dicarboxylate；Dimethyl 3-(dimethylamino)-4-methyl-5,7-dihydrocyclopenta[c]pyridine-6,6-dicarboxylate；dimethyl 3-(dimethylamino)-4-methyl-5,7-dihydrocyclopenta[c]pyridine-6,6-dicarboxylate
• CAS: 1360557-09-0
• 化学式: C₁₅H₂₀N₂O₄
• 分子量: 292.335
• InChiKey: FEEDJHACUFCEKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二甲基氢胺 、 dimethyl 2-(but-2-ynyl)-2-(prop-2-ynyl)malonate 在 bis(1,5-cyclooctadiene)nickel (0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以86%的产率得到dimethyl 3-(dimethylamino)-4-methyl-5H-cyclopenta[c]-pyridine-6,6(7H)-dicarboxylate
  参考文献：
  名称：

  一个偶然的发现：用于二炔与未活化腈环加成的镍催化剂

  摘要：

  在关键时刻！[Ni(cod) 2 ]（cod=1,5-环辛二烯）和配体4,5-双（二苯基膦）-9,9-二甲基呫吨（Xantphos）的催化组合用于获得吡啶（见方案）。反应在环境条件下进行以提供极好的产物产率。还提供了这种催化剂与其他最先进催化剂的比较。

  DOI：

  10.1002/anie.201104475

文献信息

• Iron-Catalyzed Cycloaddition Reaction of Diynes and Cyanamides at Room Temperature
  作者：Chunxiang Wang、Dongping Wang、Fen Xu、Bin Pan、Boshun Wan

  DOI：10.1021/jo400057t

  日期：2013.4.5

  An iron-catalyzed [2 + 2 + 2] cycloaddition reaction of diynes and cyanamides at room temperature is reported. Highly substituted 2-aminopyridines were obtained in good to excellent yields with high regioselectivity. Insights toward the reaction process were investigated through in situ IR spectra and control experiments. In this iron-catalyzed cycloaddition reaction, the active iron species was generated only in the presence of both alkynes and nitriles. The lower reaction temperature, broad substrates scope, and inversed regioselectivity make it a complementary method to the previously developed iron catalytic system.
• A Serendipitous Discovery: Nickel Catalyst for the Cycloaddition of Diynes with Unactivated Nitriles
  作者：Puneet Kumar、Simon Prescher、Janis Louie

  DOI：10.1002/anie.201104475

  日期：2011.11.4

  9‐dimethylxanthene (Xantphos) was used to access pyridines (see scheme). The reaction proceeds under ambient conditions to provide excellent yields of the products. Comparison of this catalyst with the other state‐of‐the‐art catalysts is also provided.

  在关键时刻！[Ni(cod) 2 ]（cod=1,5-环辛二烯）和配体4,5-双（二苯基膦）-9,9-二甲基呫吨（Xantphos）的催化组合用于获得吡啶（见方案）。反应在环境条件下进行以提供极好的产物产率。还提供了这种催化剂与其他最先进催化剂的比较。