4-(3,4-dihydroisoquinolin-2(1H)-yl)butan-2-one | 3651-88-5

• 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: 4-(3,4-dihydroisoquinolin-2(1H)-yl)butan-2-one
• 英文别名: 4-(3,4-dihydroisoquinolin-2(2H)-yl)butan-2-one；4-(3,4-dihydro-1H-[2]isoquinolyl)-butan-2-one；4-(3,4-Dihydro-1H-[2]isochinolyl)-butan-2-on；1-Methyl-3-<1,2,3,4-tetrahydro-isochinolyl-(2)>-propan-1-on；4-(3,4-dihydro-1H-isoquinolin-2-yl)butan-2-one
• CAS: 3651-88-5
• 化学式: C₁₃H₁₇NO
• mdl: MFCD03011606
• 分子量: 203.284
• InChiKey: XNDPPXXLNZOULZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3,4-dihydroisoquinolin-2(1H)-yl)butan-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-(3,4-dihydroisoquinolin-2(1H)-yl)butan-2-ol
  参考文献：
  名称：

  Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines

  摘要：

  1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)(3)Cl-2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Delta(3)-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate alpha,beta-unsaturated iminium ion prior to oxazine formation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.031
• 作为产物：
  描述：

  四氢异喹啉 、 丁烯酮 生成 4-(3,4-dihydroisoquinolin-2(1H)-yl)butan-2-one
  参考文献：
  名称：

  Visible light photooxidative cyclization of amino alcohols to 1,3-oxazines

  摘要：

  1,3-Amino alcohols were prepared to examine how structure affects the oxidation of tertiary amines in visible light photocatalysis. These substrates were cyclized to produce oxazines following the photooxidative formation of iminium ions using catalytic Ru(bpy)(3)Cl-2. Amino alcohol derivatives of tetrahydroisoquinoline, tetrahydroquinoline, pyrrolidine, and Delta(3)-piperidine all were found to be viable substrates. In the case of the unsaturated piperidines, cyclization is accompanied by addition of methanol across the alkene; most likely occurring via a conjugate addition to an intermediate alpha,beta-unsaturated iminium ion prior to oxazine formation. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.031

文献信息

• Mild Metal-Free Intramolecular Oxidative Alkylation of a C_<i>sp</i>3H Bond Adjacent to a Nitrogen Atom: A Versatile Approach to Ring-Fused Tetrahydroquinolines
  作者：Gen Zhang、Shoulei Wang、Yunxia Ma、Weidong Kong、Rui Wang

  DOI：10.1002/adsc.201200731

  日期：2013.3.25

  A metal‐free intramolecular oxidative cross‐coupling reaction for the constructing Csp3Csp3 bonds mediated by 2,3‐dichloro‐5,6‐dicyanobenzoquinone (DDQ) under mild conditions was realized for the first time. This novel strategy provides a simple, efficient, and environmentally friendly access to diverse ring‐fused tetrahydroquinoline derivatives.

  无金属的分子内氧化性交叉耦合的构造下反应SP 3  Ç SP 3个温和的条件下通过2,3-二氯-5,6-二氰基苯醌（DDQ）介导的键被首次实现。这种新颖的策略提供了一种简单，高效且对环境友好的方法，可轻松获得各种环稠合的四氢喹啉衍生物。
• Alternative tandem cyclisation pathways in the reaction between imines and enones
  作者：P. Ricardo Girling、Andrei S. Batsanov、Adam D.J. Calow、Hong C. Shen、Andrew Whiting

  DOI：10.1016/j.tet.2016.01.006

  日期：2016.2

  reduced dihydropyridine formation, and instead, a trimerisation reaction of the methoxyvinyl methyl ketone occurs, to give 1,3,5-triacetylbenzene from a different formal [2+2+2]-cycloaddition. The formal [4+2]-cycloaddition reaction of methoxyvinyl methylketone requires a cyclic imine in order to form the dihydropyridine because the reaction with acyclic imines produced a dihydropyridine from a formal

  在路易斯酸性条件下或纯净条件下，二氢异喹啉与Danishefsky的二烯反应，生成低至中等产率的正式aza-Diels-Alder [4 + 2]-环加合物。但是，在路易斯酸催化下使用甲氧基乙烯基甲基酮并不能得到aza-Diels-Alder加合物，而是发生了正式的[2 + 2 + 2]-环加成反应，从而获得了二乙酰基二氢吡啶。路易斯酸负荷增加导致二氢吡啶的形成减少，相反，发生甲氧基乙烯基甲基酮的三聚反应，从而由不同的[2 + 2 + 2]-环加成反应生成1,3,5-三乙酰基苯。甲氧基乙烯基甲基酮的正式[4 + 2]-环加成反应需要环状的亚胺才能形成二氢吡啶，因为与无环亚胺的反应是由正式的[1 + 2 + 1 + 2]-环加成产生二氢吡啶的。3，4-二氢异喹啉和甲基乙烯基酮，由氧-亲路易斯酸催化，通过曼尼希-迈克尔途径和亚铵离子物种进行。所有反应均通过一锅级联途径进行。
• KR1020/200145661
  申请人：——

  公开号：——

  公开（公告）日：——
• t-Aminoalkyl Derivatives of 2-Aminothiazole
  作者：A. H. Land、Carl Ziegler、James M. Sprague

  DOI：10.1021/ja01193a035

  日期：1947.1
• Selective Anticancer Therapy Based on a HA-CD44 Interaction Inhibitor Loaded on Polymeric Nanoparticles
  作者：José M. Espejo-Román、Belén Rubio-Ruiz、Victoria Cano-Cortés、Olga Cruz-López、Saúl Gonzalez-Resines、Carmen Domene、Ana Conejo-García、Rosario M. Sánchez-Martín

  DOI：10.3390/pharmaceutics14040788

  日期：——

  Hyaluronic acid (HA), through its interactions with the cluster of differentiation 44 (CD44), acts as a potent modulator of the tumor microenvironment, creating a wide range of extracellular stimuli for tumor growth, angiogenesis, invasion, and metastasis. An innovative antitumor treatment strategy based on the development of a nanodevice for selective release of an inhibitor of the HA-CD44 interaction is presented. Computational analysis was performed to evaluate the interaction of the designed tetrahydroisoquinoline-ketone derivative (JE22) with CD44 binding site. Cell viability, efficiency, and selectivity of drug release under acidic conditions together with CD44 binding capacity, effect on cell migration, and apoptotic activity were successfully evaluated. Remarkably, the conjugation of this CD44 inhibitor to the nanodevice generated a reduction of the dosis required to achieve a significant therapeutic effect.