1-methyl-3,4-diphenyl-6,7-dihydro-5H-cyclopenta[c]pyridine | 151724-34-4

• 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: 1-methyl-3,4-diphenyl-6,7-dihydro-5H-cyclopenta[c]pyridine
• CAS: 151724-34-4
• 化学式: C₂₁H₁₉N
• 分子量: 285.389
• InChiKey: PFLCTXPXXCVYED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  1-methyl-3,4-diphenyl-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 24.0h， 以66%的产率得到1-Methyl-3,4-diphenyl-6,7-dihydro-5H-[2]pyrindine 2-oxide
  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：

  1-(1-吡咯烷)环戊烯 、 3-甲基-5,6-二苯基-1,2,4-三嗪 反应 16.0h， 以78%的产率得到1-methyl-3,4-diphenyl-6,7-dihydro-5H-cyclopenta[c]pyridine
  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

文献信息

• Synthesis of Pyridines from Ketoximes and Terminal Alkynes via C–H Bond Functionalization
  作者：Rhia M. Martin、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/jo202280e

  日期：2012.3.2

  An expedient one-pot rhodium catalyzed C–H bond functionalization/electrocyclization/dehydration procedure has been developed for the synthesis of highly substituted pyridine derivatives from terminal alkynes and α,β-unsaturated ketoximes. The use of electron-deficient phosphite ligands is important to suppress dimerization of the terminal alkynes to enynes.

  已经开发了一种方便的一锅铑催化的 C-H 键官能化/电环化/脱水程序，用于从末端炔烃和 α,β-不饱和酮肟合成高度取代的吡啶衍生物。缺电子亚磷酸酯配体的使用对于抑制末端炔烃向烯炔烃的二聚化很重要。
• Rhodium-Catalyzed One-Pot Synthesis of Substituted Pyridine Derivatives from α,β-Unsaturated Ketoximes and Alkynes
  作者：Kanniyappan Parthasarathy、Masilamani Jeganmohan、Chien-Hong Cheng

  DOI：10.1021/ol7028367

  日期：2008.1.1

  A rhodium-catalyzed chelation-assisted CA activation of alpha,beta-unsaturated ketoximes and the reaction with alkynes to afford highly substituted pyridine derivatives is described.
• 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.