4,5-dihydro-3,3a-diaza-cyclopenta[c]phenanthrene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-dihydro-3,3a-diaza-cyclopenta[c]phenanthrene
• 英文别名: 13,14-Diazatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2,4,6,8,14,16-heptaene；13,14-diazatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2,4,6,8,14,16-heptaene
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: ITHXVOIEVJXNNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-碘萘 、 1-(2-溴乙基)-1H-吡唑 在 palladium diacetate 降冰片烯 、 三(2-呋喃基)膦 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 以51%的产率得到4,5-dihydro-3,3a-diaza-cyclopenta[c]phenanthrene
  参考文献：
  名称：

  Preparation of Annulated Nitrogen-Containing Heterocycles via a One-Pot Palladium-Catalyzed Alkylation/Direct Arylation Sequence

  摘要：

  A palladium-catalyzed/norbornene-mediated sequential coupling reaction involving an aromatic Sp(2) C-H functionalization as the key step is described, in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one pot. A variety of highly substituted six- and seven-membered annulated pyrroles and pyrazoles were synthesized in a one-step process in good yields from readily accessible N-bromoalkyl pyrroles or pyrazoles and aryl iodides.

  DOI：

  10.1021/ol060447y

文献信息

• Preparation of Annulated Nitrogen-Containing Heterocycles via a One-Pot Palladium-Catalyzed Alkylation/Direct Arylation Sequence
  作者：Christophe Blaszykowski、Evangelos Aktoudianakis、Cyril Bressy、Dino Alberico、Mark Lautens

  DOI：10.1021/ol060447y

  日期：2006.5.1

  A palladium-catalyzed/norbornene-mediated sequential coupling reaction involving an aromatic Sp(2) C-H functionalization as the key step is described, in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one pot. A variety of highly substituted six- and seven-membered annulated pyrroles and pyrazoles were synthesized in a one-step process in good yields from readily accessible N-bromoalkyl pyrroles or pyrazoles and aryl iodides.
• A Palladium-Catalyzed Alkylation/Direct Arylation Synthesis of Nitrogen-Containing Heterocycles
  作者：Christophe Blaszykowski、Evangelos Aktoudianakis、Dino Alberico、Cyril Bressy、David G. Hulcoop、Farnaz Jafarpour、Arash Joushaghani、Benoît Laleu、Mark Lautens

  DOI：10.1021/jo702052b

  日期：2008.3.1

  [Graphics]A norbornene-mediated palladium-catalyzed sequence is described in which an alkyl-aryl bond and an aryl-heteroaryl bond are formed in one reaction vessel. The aryl-heteroaryl bond-forming step occurs via a direct arylation reaction. A number of six-, seven-, and eight-membered ring-annulated indoles, pyrroles, pyrazoles, and azaindoles were synthesized from the corresponding bromoalkyl azole and an aryl iodide.