1-(isoquinolin-4-yl)propan-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1-(isoquinolin-4-yl)propan-2-one
• 英文别名: 1-Isoquinolin-4-ylpropan-2-one
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: UYWJIOLWQIEBKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴异喹啉 、 乙酸异丙烯酯 在 tris(dibenzylideneacetone)dipalladium (0) 、 三正丁基甲氧基锡 、 2-二苯基磷-2'-(N,N-二甲氨基)联苯 作用下， 以 甲苯 为溶剂， 以90%的产率得到1-(isoquinolin-4-yl)propan-2-one
  参考文献：
  名称：

  A highly active catalyst system for the heteroarylation of acetone

  摘要：

  A highly active catalyst system for the heteroarylation of acetone has been identified. The Coupling between the in situ generated tributyltin enolate of acetone and a variety of heteroaromatic bromides, chlorides, and triflates in the presence of this catalyst system provided arylacetones in good yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.176

文献信息

• Regioselective C−H Functionalization of Heteroarene <i>N</i> ‐Oxides Enabled by a Traceless Nucleophile
  作者：Gangadhar Rao Mathi、Byeongseok Kweon、Yonghoon Moon、Yujin Jeong、Sungwoo Hong

  DOI：10.1002/anie.202010597

  日期：2020.12.7

  simultaneous C8‐functionalization of quinolines at room temperature. Experimental and computational studies support the traceless operation of a nucleophile, which enables the previously inaccessible transformation of N‐alkenoxyheteroarenium salts. Remarkably, the generality of this strategy has been further demonstrated by broad applications in the regioselective C−H functionalization of other electron‐deficient

  尽管N-烯氧基氧杂芳烃盐已广泛用作亲核（杂）芳烃的本体合成子，但对贫电子杂芳烃的使用仍未探索。为了克服喹啉盐固有的电子缺陷，设计了一种无痕亲核试剂触发的策略，其中，喹啉段被转化为脱芳构的中间体，从而允许在室温下同时对喹啉进行C8功能化。实验和计算研究支持亲核试剂的无痕操作，这使以前无法实现的N-烯氧基氧杂芳烃盐转化成为可能。值得注意的是，该策略的普遍性已在其他电子缺陷型杂芳烃（如菲啶）的区域选择性C-H官能化中得到广泛应用，从而得到进一步证明。
• A facile, microwave-assisted, palladium-catalyzed arylation of acetone
  作者：Harry R. Chobanian、Ping Liu、Marc D. Chioda、Yan Guo、Linus S. Lin

  DOI：10.1016/j.tetlet.2006.12.060

  日期：2007.2

  We report an expedient method for the heteroarylation of acetone tinder tin-free conditions. The coupling is performed using the commercially available enol silane of acetone (2-trimethylsilyloxypropene) and a corresponding ary, bromide, chloride or triflate under microwave-assisted conditions, with tris(dibenzylideneacetonc)dipalladium (Pd-2(dba)(3)) or palladium acetate (Pd(OAc)(2)) and 2-(2',6'-dimethoxybiphenyl)dicyclohexylphosphine (S-Phos) as the catalyst system. Published by Elsevier Ltd.
• A highly active catalyst system for the heteroarylation of acetone
  作者：Ping Liu、Thomas J. Lanza、James P. Jewell、Carrie P. Jones、William K. Hagmann、Linus S. Lin

  DOI：10.1016/j.tetlet.2003.09.176

  日期：2003.12

  A highly active catalyst system for the heteroarylation of acetone has been identified. The Coupling between the in situ generated tributyltin enolate of acetone and a variety of heteroaromatic bromides, chlorides, and triflates in the presence of this catalyst system provided arylacetones in good yields. (C) 2003 Elsevier Ltd. All rights reserved.