N-benzyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide | 1361098-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: N-benzyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide
• 英文别名: 2-phenyl-N-(tosylmethyl)-1,2,3,4-tetrahydroisoquinoline-1-carbohydrazide
• CAS: 1361098-19-2
• 化学式: C₂₃H₂₂N₂O
• 分子量: 342.44
• InChiKey: MVXCZPXBJUQWAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.11
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.34
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-benzyl-N-(1,3-dioxoisoindolin-2-yl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以77%的产率得到N-benzyl-2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-carboxamide
  参考文献：
  名称：

  亚胺离子和N-羟基酰亚胺作为DEAD促进的氧化Ugi变体中的替代成分

  摘要：

  使用源自叔胺的亚胺离子作为亚胺替代物，使用N-羟基酰亚胺作为酸替代物和使用DEAD作为氧化剂，已有效地实现了实用的无金属氧化Ugi型三组分组件。该双重替代物Ugi变体以较宽的底物范围和所需的官能团耐受性进行，从而以良好的分离产率产生了宽范围的N-烷基-N-酰基氨基邻苯二酰亚胺和N-烷基-N-酰基氨基琥珀酰亚胺衍生物。

  DOI：

  10.1021/acs.joc.8b01868

文献信息

• DEAD-Promoted Oxidative Ugi-Type Reaction Including an Unprecedented Ugi Amidation Assisted by Dicarboxylic Acids
  作者：Jiankun Wang、Yilin Sun、Guangji Wang、Le Zhen

  DOI：10.1002/ejoc.201701323

  日期：2017.11.16

  A mild and metal-free DEAD-promoted oxidative Ugi-type reaction of tertiary amines has been demonstrated, giving facile access to α-amino amides and imides with diverse functional groups in good isolated yields. This Ugi-type approach achieves an unprecedented synthesis of α-amino amide analogues with the assistance of dicarboxylic acids, but not water, for the introduction of carbonyl oxygen of the

  已经证明了温和且无金属的 DEAD 促进的叔胺氧化 Ugi 型反应，可以轻松获得具有不同官能团的 α-氨基酰胺和酰亚胺，并具有良好的分离产率。这种 Ugi 类型的方法在二羧酸的帮助下实现了前所未有的 α-氨基酰胺类似物合成，而不是水，用于引入酰胺部分的羰基氧。机理研究表明，二元羧酸很容易发生分子内环化，而不是 Mumm 重排，从而提供所需的酰胺，同时释放一分子酸酐。
• Bodipy-Based Metal–Organic Frameworks Transformed in Solid States from 1D Chains to 2D Layer Structures as Efficient Visible Light Heterogeneous Photocatalysts for Forging C–B and C–C Bonds
  作者：Qingchun Xia、Jingli Yang、Suzhen Zhang、Jie Zhang、Zhiyong Li、Jianji Wang、Xuenian Chen

  DOI：10.1021/jacs.2c11647

  日期：2023.3.22

  the porous frameworks, both BMOF 2D and BMON 2D displayed high reactivity and recyclability in the photocatalytic inverse hydroboration and cross-dehydrogenative coupling reactions to afford α-amino organoborons and α-amino amides in moderate to high yields. This work not only highlights the cascade utilization of ligand installation and ultrasonic liquid exfoliation methods to provide the single-layer

  硼二吡咯亚甲基（也称为 bodipy）作为一类多功能且稳健的荧光团和卟啉的结构类似物，在光捕获和能量转移过程领域引起了极大的兴趣。然而，将 bodipy 单体制备成金属有机框架 (MOF) 及其潜力的开发仍然落后于卟啉 MOF。在这项工作中，两个基于硼二吡咯的 MOF，具有一维链结构的BMOF 1D和具有二维层结构的 BMOF 2D，通过使用二羧基功能化的硼二吡啶配体组装而成。BMOF 1D也可以通过将额外的配体插入BMOF 1D转化为 BMOF 2D将相邻的链交联到菱形网格层中。在此过程中，自发剥离同时发生，形成数百纳米厚度的 BMOF 2D (nBMOF 2D )，可通过超声波液体剥离法在高温下进一步剥离成单层 MOF 纳米片 (BMON 2D )屈服。BMOF 2D和 BMON 2D多孔框架中具有独特的 bodipy 支架在光催化反硼氢化反应和交叉脱氢偶联反应中表现出高反应性和可回收
• A Comparative Mechanistic Study of Cu-Catalyzed Oxidative Coupling Reactions with <i>N</i>-Phenyltetrahydroisoquinoline
  作者：Esther Boess、Corinna Schmitz、Martin Klussmann

  DOI：10.1021/ja211697s

  日期：2012.3.21

  A comparative mechanistic study of Cu-catalyzed oxidative coupling reactions of N-phenyltetrahydroisoquinoline with different nucleophiles was conducted. Two previously reported combinations of catalyst and oxidant were studied, CuCl2 center dot 2H(2)O/O-2 and CuBr/tert-butyl hydroperoxide (TBHP). On the basis of a synthetic study with different nucleophiles, the electrophilicity of the intermediate iminium ion was estimated and differences between the two methods were revealed. The key intermediate in the aerobic method is shown to be an iminium ion, formed through oxidation by copper(II), which can react with any nudeophile of sufficient reactivity. The role of oxygen is the reoxidation of the reduced catalyst. In the CuBr/TBHP system, an alpha-amino peroxide is proposed as a true intermediate within the catalytic cycle, formed from the amine and TBHP by a Cu-catalyzed radical reaction pathway and acting as a precursor to the iminium ion intermediate.