dimethyl 1,4-dimethyl-3-(methyl(phenyl)amino)-5H-cyclopenta-[c]pyridine-6,6(7H)-dicarboxylate | 1323947-62-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dimethyl 1,4-dimethyl-3-(methyl(phenyl)amino)-5H-cyclopenta-[c]pyridine-6,6(7H)-dicarboxylate
• 英文别名: dimethyl 1,4-dimethyl-3-(N-methylanilino)-5,7-dihydrocyclopenta[c]pyridine-6,6-dicarboxylate
• CAS: 1323947-62-1
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: VQFRWKBYZCDHBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  N-甲基苯胺 在 bis(1,5-cyclooctadiene)nickel (0) 、 1,3-bis(2,4,6-trimethylphenyl)imidazolidine 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 0.5h， 生成 dimethyl 1,4-dimethyl-3-(methyl(phenyl)amino)-5H-cyclopenta-[c]pyridine-6,6(7H)-dicarboxylate
  参考文献：
  名称：

  镍催化二炔和氰胺的[2+2+2]环加成反应

  摘要：

  通过镍催化的[2+2+2]环加成反应，由二炔和氰胺制备了多种双环N,N-二取代2-氨基吡啶。该反应在室温下以低催化剂负载量进行，以良好至优异的收率提供2-氨基吡啶。该方法适用于内部二炔和末端二炔，并以区域选择性方式进行。使用了许多具有不同官能团耐受性的氰胺。使用3-己炔和N-氰基吡咯烷的分子间形式也以良好的收率提供了所需的N,N-二取代的2-氨基吡啶。

  DOI：

  10.1002/ejoc.201100428

文献信息

• Iridium-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Cyanamides
  作者：Toru Hashimoto、Satoshi Ishii、Reiko Yano、Hiroki Miura、Ken Sakata、Ryo Takeuchi

  DOI：10.1002/adsc.201500637

  日期：2015.12.14

  the [2+2+2] cycloaddition of α,ω-diynes with cyanamides. A wide range of cyanamides derived from secondary amines are good coupling partners for α,ω-diynes. The reaction of unsymmetrical α,ω-diynes possessing two different internal alkyne moieties with cyanamides is regioselective. A competitive experiment showed that cyanamide is more reactive than nitrile. This higher reactivity of cyanamide than

  络合物[Ir（cod）Cl] 2 / DPPF或rac -BINAP是α，ω-二炔与氰酰胺环[2 + 2 + 2]环加成的有效催化剂。多种衍生自仲胺的氰胺是α，ω-二炔的良好偶联伙伴。具有两个不同内部炔烃部分的不对称α，ω-二炔与氰胺的反应是区域选择性的。一项竞争性实验表明，氰胺比腈更具反应性。根据密度泛函理论（DFT）计算，在B3LYP水平上分析了比腈更高的氰酰胺反应性。
• 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.
• Iron-Catalyzed Formation of 2-Aminopyridines from Diynes and Cyanamides
  作者：Timothy K. Lane、Brendan R. D’Souza、Janis Louie

  DOI：10.1021/jo3012418

  日期：2012.9.7

  Diynes and cyanamides undergo an iron-catalyzed [2 + 2 + 2] cycloaddition to form highly substituted 2-aminopyridines in an atom-efficient manner that is both high yielding and regioselective. This system was also used to cyclize two terminal alkynes and a cyanamide to afford a 2,4,6-trisubstituted pyridine product regioselectively.
• Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides
  作者：Ryan M. Stolley、Michael T. Maczka、Janis Louie

  DOI：10.1002/ejoc.201100428

  日期：2011.7

  A variety of bicyclic N,N-disubstituted 2-aminopyridines have been prepared from diynes and cyanamides by nickel-catalyzed [2+2+2] cycloaddition reactions. The reactions proceeded at room temperature with low catalyst loading to afford 2-aminopyridines in good to excellent yields. The method is amenable to both internal and terminal diynes and proceeds in a regioselective manner. A number of cyanamides

  通过镍催化的[2+2+2]环加成反应，由二炔和氰胺制备了多种双环N,N-二取代2-氨基吡啶。该反应在室温下以低催化剂负载量进行，以良好至优异的收率提供2-氨基吡啶。该方法适用于内部二炔和末端二炔，并以区域选择性方式进行。使用了许多具有不同官能团耐受性的氰胺。使用3-己炔和N-氰基吡咯烷的分子间形式也以良好的收率提供了所需的N,N-二取代的2-氨基吡啶。