4-phenyl-6,7-dihydro-5H-cyclopenta[c]pyridine | 151724-25-3

• 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: 4-phenyl-6,7-dihydro-5H-cyclopenta[c]pyridine
• 英文别名: 4-phenyl-6,7-dihydro-5H-2-pyrindine；4-Phenyl-2-pyrindan
• CAS: 151724-25-3
• 化学式: C₁₄H₁₃N
• 分子量: 195.264
• InChiKey: PPBMUEWVQWGJNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  350.1±31.0 °C(predicted)
• 密度：
  1.102±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  4-phenyl-6,7-dihydro-5H-cyclopenta[c]pyridine 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 4-phenyl-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-(1-hydroxy-1-phenylethyl)cyclopentene-1-carboxaldehyde N,N-dimethylhydrazone 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 21.0h， 以86%的产率得到4-phenyl-6,7-dihydro-5H-cyclopenta[c]pyridine
  参考文献：
  名称：

  2-溴环戊烯-1-甲醛中的5 H -2-嘧啶

  摘要：

  2-溴环戊烯-1-甲醛N，N-二甲基hydr 1与乙烯基锌卤化物以及2-呋喃基和2-噻吩基锌卤化物的钯（0）催化偶联为相应的2-乙烯基-和2-杂芳基-提供了一条途径环戊烯-1-羧甲醛二甲基hydr。它们热环化成6，7-二氢-5 H -2-吡啶啉（例如3）。

  DOI：

  10.1016/0040-4020(95)00509-7

文献信息

• Synthesis of annulated pyridines as inhibitors of aldosterone synthase (CYP11B2)
  作者：Rainer E. Martin、Johannes Lehmann、Thibaut Alzieu、Mario Lenz、Marjorie A. Carnero Corrales、Johannes D. Aebi、Hans Peter Märki、Bernd Kuhn、Kurt Amrein、Alexander V. Mayweg、Robert Britton

  DOI：10.1039/c6ob00848h

  日期：——

  A series of cyclopenta[c]pyridine aldosterone synthase (AS) inhibitors were conveniently accessed using batch or continuous flow Kondrat'eva reactions. Preparation of the analogous cyclohexa[c]pyridines led to the identification of a potent and more selective AS inhibitor. The structure-activity-relationship (SAR) in this new series was rationalized using binding mode models in the crystal structure

  使用分批或连续流Kondrat'eva反应可方便地获得一系列环戊基[ c ]吡啶醛固酮合酶（AS）抑制剂。相似的环己基[ c ]吡啶的制备导致鉴定出有效的且更具选择性的AS抑制剂。在AS晶体结构中使用结合模式模型合理化了这个新系列中的结构活性关系（SAR）。
• The Kondrat’eva Reaction in Flow: Direct Access to Annulated Pyridines
  作者：Johannes Lehmann、Thibaut Alzieu、Rainer E. Martin、Robert Britton

  DOI：10.1021/ol4013525

  日期：2013.7.19

  A continuous flow inverse-electron-demand Kondrat'eva reaction has been developed that provides direct access to cycloalka[c]pyridines from unactivated oxazoles and cycloalkenes. Annulated pyridines obtained by this one-step process are valuable scaffolds for medicinal chemistry.
• 5H-2-Pyrindines From 2-Bromocyclopentene-1-carboxaldehyde
  作者：Thomas L. Gilchrist、Paul D. Kemmitt、Andrew L. Germain

  DOI：10.1016/0040-4020(95)00509-7

  日期：1995.8

  The palladium(0) catalysed coupling of 2-bromocyclopentene-1-carboxaldehyde N,N-dimethylhydrazone 1 with vinylzinc halides and with 2-furyl- and 2-thicnylzinc halides provides a route to the corresponding 2-vinyl- and 2-heteroaryl-cyclopentene-1-carboxaldehyde dimethylhydrazones. These cyclise thermally to 6,7-dihydro-5H-2-pyrindines (e.g., 3).

  2-溴环戊烯-1-甲醛N，N-二甲基hydr 1与乙烯基锌卤化物以及2-呋喃基和2-噻吩基锌卤化物的钯（0）催化偶联为相应的2-乙烯基-和2-杂芳基-提供了一条途径环戊烯-1-羧甲醛二甲基hydr。它们热环化成6，7-二氢-5 H -2-吡啶啉（例如3）。
• 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.