(7-Fluoro-3-phenylisoquinolin-2-ium-2-yl)-(4-methylphenyl)sulfonylazanide | 1353561-06-4

• 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: (7-Fluoro-3-phenylisoquinolin-2-ium-2-yl)-(4-methylphenyl)sulfonylazanide
• CAS: 1353561-06-4
• 化学式: C₂₂H₁₇FN₂O₂S
• 分子量: 392.454
• InChiKey: MMTCBCHXVDZLPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (7-Fluoro-3-phenylisoquinolin-2-ium-2-yl)-(4-methylphenyl)sulfonylazanide 、 ethyl 4-phenylbuta-2,3-dienoate 在 三苯基膦 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 2-benzyl-9-fluoro-5-phenylpyrazolo[5,1-a]isoquinoline-1-carboxylate
  参考文献：
  名称：

  An efficient approach to H-pyrazolo[5,1-a]isoquinolines via a silver triflate-catalyzed reaction of N′-(2-alkynylbenzylidene)hydrazide with allenoate

  摘要：

  A silver triflate-catalyzed reaction of N'-(2-alkynylbenzylidene)hydrazide with allenoate under mild conditions is described, which provides an efficient approach to diverse H-pyrazolo[5,1-alisoquinolines. This reaction proceeds with a wide substrate scope with good functional groups tolerance. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.013
• 作为产物：
  描述：

  N'-(5-fluoro-2-(phenylethynyl)benzylidene)-4-methylbenzenesulfonohydrazide 在 silver trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 生成 (7-Fluoro-3-phenylisoquinolin-2-ium-2-yl)-(4-methylphenyl)sulfonylazanide
  参考文献：
  名称：

  N'-（2-炔基亚苄基）酰肼的银（I）催化闭环合成异喹啉鎓-2-基酰胺

  摘要：

  描述了一种从容易获得的酰肼和2-炔基苯甲醛开始合成异喹啉鎓-2-基酰胺的有效一锅方案。该方案的关键步骤是原位生成的N '-（2-炔基亚苄基）酰肼的银（I）催化的闭环反应。可以将来自叔丁氧基羰基酰肼的异喹啉鎓-2-基酰胺进一步脱保护，得到2-氨基异喹啉鎓三氟乙酸酯。 炔烃-酰肼-异喹啉-环化-酰化物-银催化

  DOI：

  10.1055/s-0030-1260219

文献信息

• Synthesis of Isoquinolinium-2-yl Amides via Silver(I)-Catalyzed Ring Closure of N′-(2-Alkynylbenzylidene)hydrazides
  作者：Denis Ermolat’ev、Erik Van der Eycken、Vsevolod Peshkov、Olga Pereshivko、Sofie Van Hove

  DOI：10.1055/s-0030-1260219

  日期：2011.10

  An efficient one-pot protocol for the synthesis of isoquinolinium-2-yl amides starting from readily available hydrazides and 2-alkynylbenzaldehydes is described. The key step of the protocol is a silver(I)-catalyzed ring-closure of N′-(2-alkynylbenzylidene)hydrazides that are generated in situ. Isoquinolinium-2-yl amides derived from tert-butoxycarbonyl hydrazide could be further deprotected, delivering

  描述了一种从容易获得的酰肼和2-炔基苯甲醛开始合成异喹啉鎓-2-基酰胺的有效一锅方案。该方案的关键步骤是原位生成的N '-（2-炔基亚苄基）酰肼的银（I）催化的闭环反应。可以将来自叔丁氧基羰基酰肼的异喹啉鎓-2-基酰胺进一步脱保护，得到2-氨基异喹啉鎓三氟乙酸酯。 炔烃-酰肼-异喹啉-环化-酰化物-银催化
• Formal [5+3] Cycloaddition of Zwitterionic Allylpalladium Intermediates with Azomethine Imines for Construction of N,O-Containing Eight-Membered Heterocycles
  作者：Chunhao Yuan、Yang Wu、Dongqi Wang、Zhenhua Zhang、Chang Wang、Leijie Zhou、Cheng Zhang、Baoan Song、Hongchao Guo

  DOI：10.1002/adsc.201701247

  日期：2018.2.15

  A formal [5+3] cycloaddition of zwitterionic allylpalladium intermediates with 1,3‐dipoles is developed, providing N,O‐containing eight‐membered heterocyclic compounds in high yields. Catalytically generated zwitterionic allylpalladium intermediates in situ from vinylethylene carbonates or vinyloxiranes acted as dipolarophile.

  开发了具有1,3-偶极子的两性离子烯丙基钯中间体的正式[5 + 3]环加成反应，可高收率地提供含N，O的八元杂环化合物。由碳酸乙烯基亚乙酯或乙烯基环氧乙烷在原位催化生成的两性离子烯丙基钯中间体起亲极性的作用。
• An efficient approach to H-pyrazolo[5,1-a]isoquinolines via a silver triflate-catalyzed reaction of N′-(2-alkynylbenzylidene)hydrazide with allenoate
  作者：Liang Gao、Shengqing Ye、Qiuping Ding、Zhiyuan Chen、Jie Wu

  DOI：10.1016/j.tet.2012.02.013

  日期：2012.4

  A silver triflate-catalyzed reaction of N'-(2-alkynylbenzylidene)hydrazide with allenoate under mild conditions is described, which provides an efficient approach to diverse H-pyrazolo[5,1-alisoquinolines. This reaction proceeds with a wide substrate scope with good functional groups tolerance. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 2-trifluoromethylpyrazolo[5,1-<i>a</i>]isoquinolines via silver triflate-catalyzed or electrophile-mediated one-pot tandem reaction
  作者：Xiaoli Zhou、Meiling Liu、Puying Luo、Yingjun Lai、Tangtao Yang、Qiuping Ding

  DOI：10.3762/bjoc.10.238

  日期：——

  An efficient one-pot tandem cyclization/[3 + 2] cycloaddition reaction of N'-(2-alkynylbenzylidene)hydrazides with ethyl 4,4,4-trifluorobut-2-ynoate under silver triflate-catalyzed or electrophile-mediated conditions is described. Various trifluoromethylated pyrazolo[5,1-a]isoquinolines were afforded in moderate to excellent yield by this developed method.

  描述了在三氟甲磺酸银催化或亲电子试剂介导的条件下，N'-(2-炔基亚苄基)肼与 4,4,4-三氟丁-2-炔酸乙酯的高效一锅串联环化/[3 + 2] 环加成反应. 通过这种开发的方法，各种三氟甲基化的吡唑并[5,1-a]异喹啉以中等至极好的收率获得。