3,4-diphenyl-6,7-dihydro-5H-[2]pyrindine | 151724-27-5

• 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: 3,4-diphenyl-6,7-dihydro-5H-[2]pyrindine
• 英文别名: 3,4-diphenyl-6,7-dihydro-5H-cyclopenta[c]pyridine
• CAS: 151724-27-5
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: UIHUDYKKJNXDOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-diphenyl-6,7-dihydro-5H-[2]pyrindine 在 过氧化氢苯甲酰 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 Acetic acid 3,4-diphenyl-6,7-dihydro-5H-[2]pyrindin-5-yl ester
  参考文献：
  名称：

  Cycloaddition Reactions with Azabenzenes, XVIII. Synthesis of [2]Pyrindines

  摘要：

  The reaction of 1,2,4-triazines (1) and 1-cyclopentenylpyrrolidine (2) afforded 6,7-dihydro-5H-[2]-pyrindines (3) in good yields. Oxidation of 3 to the N-oxides (4), reaction of 4 with acetic anhydride to 5-acetoxy-6,7-dihydro-5H-[2]pyrindines (5) and elimination of acetic acid afforded [2]pyrindines (7). 2-Methyl-2H-[2]pyrindines (9) were also prepared.

  DOI：

  10.3987/com-92-s(t)109
• 作为产物：
  描述：

  2-溴环戊烯-1-甲醛 在 palladium diacetate 、 水 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 3,4-diphenyl-6,7-dihydro-5H-[2]pyrindine
  参考文献：
  名称：

  Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes

  摘要：

  A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.

  DOI：

  10.1021/jo0105540

文献信息

• Benzannulation via the use of 1,2,4-triazines extends aromatic system of cyclometallated Pt(II) complexes to achieve candle light electroluminescence
  作者：Piotr Pander、Graeme Turnbull、Andrey V. Zaytsev、Fernando B. Dias、Valery N. Kozhevnikov

  DOI：10.1016/j.dyepig.2020.108857

  日期：2021.1

  the synthesis of novel cyclometallated Pt(II) complexes of CˆN type. It is shown that addition of a cyclopenteno unit into the complex structure not only facilitates the fabrication of efficient solution-processed OLED devices (EQEmax = 10.7 %), but also imposes structural changes leading to even more soluble derivatives. Finally, it was shown that by varying the number of fused benzene rings in the

  这项工作描述了1,2,4-三嗪方法在合成新型CˆN型环金属化Pt（II）配合物中的应用。结果表明，向复杂结构中添加环戊烯单元不仅有助于制造高效的溶液加工的OLED器件（最大EQE = 10.7％），而且还会引起结构变化，从而导致甚至更高的可溶性衍生物。最后，已表明通过改变CN稠合苯环的数目配体有可能调从绿青色（Φ发射PL = 0.15-0.43）的黄橙色（Φ PL= 0.25）。1,2,4-三嗪方法学提供了将额外的苯环融合到吡啶环中并提供含有先前未开发的大型芳族体系的配体L5的独特机会。结果表明，这种苯甲环化是实现发射红移并产生可溶液处理的单掺杂OLED器件的有效方法，该器件显示的发射光谱类似于烛光。
• Synthesis of Isoquinolines and Pyridines by the Palladium-Catalyzed Iminoannulation of Internal Alkynes
  作者：Kevin R. Roesch、Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0105540

  日期：2001.11.1

  A wide variety of substituted isoquinoline, tetrahydroisoquinoline, 5,6-dihydrobenz[f]isoquinoline, pyrindine, and pyridine heterocycles have been prepared in good to excellent yields via annulation of internal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst. The best results are obtained by employing 5 mol % of Pd(OAc)(2), an excess of the alkyne, 1 equiv of Na2CO3 as a base, and 10 mol % of PPh3 in DMF as the solvent. This annulation methodology is particularly effective for aryl- or alkenyl-substituted alkynes. When electron-rich imines are employed, this chemistry can be extended to alkyl-substituted alkynes. Trimethylsilyl-substituted alkynes also undergo this annulation process to afford monosubstituted heterocyclic products absent the silyl group.
• Cycloaddition Reactions with Azabenzenes, XVIII. Synthesis of [2]Pyrindines
  作者：Hans Neunhoeffer、Hans Neuhoeffer、Bernd Philipp、Brigit Schildhauer、Ralf Eckrich、Uwe Krichbaum

  DOI：10.3987/com-92-s(t)109

  日期：——

  The reaction of 1,2,4-triazines (1) and 1-cyclopentenylpyrrolidine (2) afforded 6,7-dihydro-5H-[2]-pyrindines (3) in good yields. Oxidation of 3 to the N-oxides (4), reaction of 4 with acetic anhydride to 5-acetoxy-6,7-dihydro-5H-[2]pyrindines (5) and elimination of acetic acid afforded [2]pyrindines (7). 2-Methyl-2H-[2]pyrindines (9) were also prepared.