2,4-diphenyl-6,7-dihidro-5H-cyclopentapyridine | 78018-73-2

• 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: 2,4-diphenyl-6,7-dihidro-5H-cyclopentapyridine
• 英文别名: 2,4-diphenyl-6,7-dihydro-5H-cyclopenta[b]pyridine；2,4-diphenyl-6,7-dihydro-5H-1-pyridine；2,3-trimethylene-4,6-diphenylpyridine；2,4-diphenyl-6,7-dihydro-5H-[1]pyrindine；2,4-Diphenyl-6,7-dihydro-5H-[1]pyrindin
• CAS: 78018-73-2
• 化学式: C₂₀H₁₇N
• 分子量: 271.362
• InChiKey: QUWRMDNZQLATSO-UHFFFAOYSA-N

物化性质

• 熔点：
  143 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  430.9±45.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 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

• 作为产物：
  描述：

  2,4-Diphenyl-5,6-dihydrocyclopenta pyrylium perchlorate 在 氨 作用下， 以63%的产率得到2,4-diphenyl-6,7-dihidro-5H-cyclopentapyridine
  参考文献：
  名称：

  Kinetics and mechanisms of nucleophilic displacements with heterocycles as leaving groups. 2. N-benzylpyridinium cations: rate variation with steric effects in the leaving group

  摘要：

  DOI：

  10.1021/jo00332a013

文献信息

• Iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines
  作者：Chunyin Zhu、Benwei Bi、Ya Ding、Te Zhang、Qiu-Yun Chen

  DOI：10.1016/j.tet.2015.10.040

  日期：2015.12

  An iodine-catalyzed aerobic oxidative formal [4+2] annulation for the construction of polyfunctionalized pyridines in one step has been developed through the green reaction system of catalytic amounts of molecular iodine and amine in combination with oxygen. Various ketones and aldehydes were able to react with different chalcones and β, γ-unsaturated α-ketoesters through this reaction strategy. Synthetically

  通过催化量的分子碘和胺与氧结合的绿色反应体系，开发了一种碘催化好氧氧化形式[4 + 2]环化反应，该环化反应可一步一步构建多官能吡啶。通过该反应策略，各种酮和醛能够与不同的查耳酮和β，γ-不饱和的α-酮酸酯反应。综合这碘催化系统可以高效率地扩大规模。
• Pd(II)-Catalyzed Synthesis of Alicyclic[<i>b</i>]-Fused Pyridines via C(sp²)–H Activation of <i>α,β</i>-Unsaturated <i>N</i>-Acetyl Hydrazones with Vinyl Azides
  作者：Biao Nie、Wanqing Wu、Chuanfei Jin、Qingyun Ren、Ji Zhang、Yingjun Zhang、Huanfeng Jiang

  DOI：10.1021/acs.joc.1c02086

  日期：2022.1.7

  A new synthetic protocol for alicyclic[b]-fused pyridines with complete regioselectivity from α,β-unsaturated N-acetyl hydrazones and vinyl azides via Pd(II)-catalyzed C–H activation/cyclization/aromatization strategy has been described. A series of five- to eight-membered alicyclic[b]-fused pyridines were prepared in a one-step manner with wide substrate scope and good functional group tolerance.

  已经描述了一种通过 Pd(II) 催化的 C-H 活化/环化/芳构化策略从α,β-不饱和N-乙酰腙和乙烯基叠氮化物具有完全区域选择性的脂环族[ b ]-稠合吡啶的新合成方案。一步法制备了一系列具有广泛底物范围和良好官能团耐受性的五至八元脂环[ b ]-稠合吡啶。
• Kinetics and mechanisms of nucleophilic displacements with heterocycles as leaving groups. Part 12. Regio- and stereo-chemistry of nucleophilic displacement and solvolysis reactions of N-(α-methylallyl)-and N-(α-phenylethyl)-pyridiniums
  作者：Alan R. Katritzky、Yu Xiang Ou、Giuseppe Musumarra

  DOI：10.1039/p29830001449

  日期：——

  N-(α-Methylallyl)pyridiniums rearrange to the N-(γ-methylallyl) analogues in a process analogous to ion return. In the tricyclic series the process (9)→(4) occurs spontaneously. In the monocyclic series (1) can be isolated and thermally rearranged into (2); this rearrangement is intramolecular. N-(α-Phenylethyl)pyridiniums solvolyse in HOAc–NEt3 with predominant inversion of configuration (90%). In

  N-（α-甲基烯丙基）吡啶以类似于离子返回的过程重排为N-（γ-甲基烯丙基）类似物。在三环系列中，过程（9）→（4）自发发生。在单环系列中，可以将（1）分离并热重排为（2）；这种重排是分子内的。在HOAc-NEt 3中的N-（α-苯乙基）吡啶溶剂化物主要反转构型（90％）。在2,4,6-三苯基系列中，这是自发发生的。分离的1-（α-苯乙基）-2-异丙基-4,6-二苯基吡啶鎓在氯苯中具有一级动力学并且具有外消旋作用。
• An Aminocatalyzed Michael Addition/Iron-Mediated Decarboxylative Cyclization Sequence for the Preparation of 2,3,4,6-Tetrasubstituted Pyridines: Scope and Mechanistic Insights
  作者：Mateus L. Stivanin、Marcelo Duarte、Camila Sartori、Naylil M. R. Capreti、Celio F. F. Angolini、Igor D. Jurberg

  DOI：10.1021/acs.joc.7b01789

  日期：2017.10.6

  A novel, scalable strategy for the preparation of 2,3,4,6-tetrasubstituted pyridines is described. This protocol has two steps: an aminocatalyzed addition of ketones to alkylidene isoxazol-5-ones, followed by an iron-mediated decarboxylative cyclization event. Mechanistic insights for both steps are provided based on HRMS-ESI(+) studies.
• Rotational equilibria in 1,2,6-trisubstituted pyridinium cations and reactions of 2-Isopropylpyrylium cations
  作者：Alan R. Katritzky、Socrates N. Vassilatos、Mateo Alajarin-Ceron

  DOI：10.1002/omr.1270211002

  日期：1983.10

  Abstract2‐Isopropyl‐6‐phenyl‐ and 2,6‐diisopropyl‐pyridiniums with bulky 1‐substituents show temperature‐variable NMR spectra which are interpreted in terms of restricted rotation. 2‐Isopropyl‐4,6‐diphenylpyrylium can be deprotonated at the isopropyl group to give an anhydro base which forms new pyryliums with electrophiles.