10-methyl-5,6-dihydro-pyrazolo[5,1-a]isoquinoline

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 10-methyl-5,6-dihydro-pyrazolo[5,1-a]isoquinoline
• 英文别名: 10-Methyl-5,6-dihydropyrazolo[5,1-a]isoquinoline；10-methyl-5,6-dihydropyrazolo[5,1-a]isoquinoline
• 化学式: C₁₂H₁₂N₂
• 分子量: 184.241
• InChiKey: UDLDVMRFEWKHRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  10-methyl-5,6-dihydro-pyrazolo[5,1-a]isoquinoline 在 ammonium cerium(IV) nitrate 、 碘 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以83%的产率得到5,6-dihydro-1-iodo-10-methylpyrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  A Palladium-Catalyzed Alkylation/Direct Arylation Synthesis of Nitrogen-Containing Heterocycles

  摘要：

  [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.

  DOI：

  10.1021/jo702052b
• 作为产物：
  描述：

  2-碘代甲苯 、 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， 反应 20.0h， 以54%的产率得到10-methyl-5,6-dihydro-pyrazolo[5,1-a]isoquinoline
  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

• Catalyst-free and oxidant-free tandem aza-Mannich/cyclization/aromatization of <i>C</i>,<i>N</i>-cyclic azomethine imines with enamides: facile synthesis of 5,6-dihydropyrazolo[5,1-<i>a</i>]isoquinolines
  作者：Hao Dong、Yongxing Zhang、Xiaochen Tian、Ruochen Pang、Weiwu Ren、Yang Wang

  DOI：10.1039/d2gc01275h

  日期：——

  tandem aza-Mannich/cyclization/aromatization reaction of C,N-cyclic azomethine imines with enamides has been developed. This practical one-step protocol enables a simple and environmentally friendly route toward the straightforward synthesis of highly substituted 5,6-dihydropyrazolo[5,1-a]isoquinolines. Different types of enamides and enamines, especially enamides derived from marketed drugs as well as bioactive

  开发了一种新型高效的无催化剂、无氧化剂串联氮杂曼尼希/环化/芳构化C , N-环偶氮甲亚胺与烯酰胺反应。这种实用的一步法为直接合成高度取代的 5,6-二氢吡唑并[5,1- a ] 异喹啉提供了一种简单且环保的途径。不同类型的烯酰胺和烯胺，尤其是衍生自上市药物以及生物活性分子的烯酰胺，是合适的底物。CB1 大麻素受体拮抗剂可以基于该方法有效合成，说明这将是合成有价值的结构基序的实用策略。