methyl 4-(isoquinolin-1-yl)-2-methylene-3-phenylbutanoate | 1334333-45-7

• 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: methyl 4-(isoquinolin-1-yl)-2-methylene-3-phenylbutanoate
• CAS: 1334333-45-7
• 化学式: C₂₁H₁₉NO₂
• 分子量: 317.387
• InChiKey: SGUAGOLEYGHICV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-甲基异喹啉 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 methyl 4-(isoquinolin-1-yl)-2-methylene-3-phenylbutanoate
  参考文献：
  名称：

  Direct one-pot introduction of 2-methylpyridines to Baylis–Hillman adducts via base-mediated 3-aza-Cope rearrangement

  摘要：

  An efficient and regioselective introduction method of 2-methylpyridines to the secondary position of Baylis-Hillman adducts has been developed. A base treatment of 2-methylpyridinium salt of Baylis-Hillman bromide generated N-allylenamine intermediate which underwent a facile 3-aza-Cope rearrangement under mild conditions to produce the product. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.101

文献信息

• Direct C(sp³)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement
  作者：Siyu Wang、Lianyou Zheng、Shutao Wang、Shulin Ning、Zhuoqi Zhang、Jinbao Xiang

  DOI：10.3762/bjoc.17.167

  日期：——

  base- and catalyst-free C(sp3)–H allylic alkylation of 2-alkylpyridines with Morita–Baylis–Hillman (MBH) carbonates is described. A plausible mechanism of the reaction might involve a tandem SN2’ type nucleophilic substitution followed by an aza-Cope rearrangement. Various alkyl substituents on 2-alkylpyridines were tolerated in the reaction to give the allylation products in 26–91% yields. The developed

  描述了 2-烷基吡啶与 Morita-Baylis-Hillman (MBH) 碳酸酯的无碱和无催化剂的 C(sp 3 )-H 烯丙基烷基化反应。该反应的一个合理机制可能涉及串联 S N 2' 型亲核取代，然后是氮杂-科普重排。在反应中可以容忍 2-烷基吡啶上的各种烷基取代基，以 26-91% 的产率得到烯丙基化产物。所开发的方法为 2-烷基吡啶衍生物的烯丙基官能化提供了一种直接且操作简单的策略。
• Enantioselective Lewis base catalysed allylation of picoline- and quinaldine-based latent pronucleophiles
  作者：Markus Lange、Nikita Alistratov、Ivan Vilotijevic

  DOI：10.1039/d4ob01063a

  日期：——

  Picolines and quinaldines are valuable building blocks and intermediates in the synthesis of natural products and pharmaceuticals. Functionalization of the methyl group in picolines and quinaldines under mild conditions is challenging. We report that the concept of latent pronucleophiles enables Lewis base catalysed allylation of picolines and quinaldines with allylic fluorides starting from silylated

  甲基吡啶和喹哪啶是天然产物和药物合成中有价值的结构单元和中间体。在温和条件下甲基吡啶和喹哪啶中的甲基官能化具有挑战性。我们报道，潜在亲核试剂的概念使得路易斯碱催化甲基吡啶和喹哪啶与烯丙基氟化物从甲硅烷基化的甲基吡啶和喹哪啶开始烯丙基化。当使用手性路易斯碱催化剂时，反应提供对映体富集的烯丙基化产物。烯丙基化产物可以快速转化为喹嗪-4-酮。