3,4-diphenyl-N-(quinolin-8-yl)butanamide | 1453491-68-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,4-diphenyl-N-(quinolin-8-yl)butanamide
• CAS: 1453491-68-3
• 化学式: C₂₅H₂₂N₂O
• 分子量: 366.462
• InChiKey: BTTFMJSVKGMWLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  597.0±45.0 °C(predicted)
• 密度：
  1.201±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.59
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.99
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  碘苯二乙酸 、 4-phenyl-N-(quinolin-8-yl)butanamide 在 双(乙腈)氯化钯(II) 、 caesium carbonate 作用下， 以 均三甲苯 为溶剂， 以60%的产率得到3,4-diphenyl-N-(quinolin-8-yl)butanamide
  参考文献：
  名称：

  Palladium-Catalyzed Cs₂CO₃-Promoted Arylation of Unactivated C(sp³)–H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation

  摘要：

  PdCl2(CH3CN)(2)-catalyzed arylation of unactivated C(sp(3))-H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp(3))-H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.

  DOI：

  10.1021/acs.joc.5b00111

文献信息

• Palladium-Catalyzed Base-Promoted Arylation of Unactivated C(sp³)-H Bonds by Aryl Iodides: A Practical Approach To Synthesize β-Aryl Carboxylic Acid Derivatives
  作者：Quan Gou、Gang Liu、Lanxiu Zhou、Suiyun Chen、Jun Qin

  DOI：10.1002/ejoc.201701215

  日期：2017.11.16

  A highly efficient protocol for the β-arylation of carboxylic amides by aryl iodides under PdCl2(CH3CN)2/CsOAc catalysis was developed. This method was found to tolerate a broad scope of substrates and was successfully employed in the preparation of a variety of β-aryl α-amino and γ-amino acid derivatives. The utility of this method was further illustrated in the synthesis of the psychotropic drug

  开发了一种高效的方案，用于在 PdCl2(CH3CN)2/CsOAc 催化下芳基碘化物对羧酰胺进行 β-芳基化。发现该方法可耐受广泛的底物，并成功用于制备各种 β-芳基 α-氨基和 γ-氨基酸衍生物。这种方法的效用在精神药物 (±)-phenibut 和 β-芳基胆汁酸类似物的合成中得到了进一步说明。
• Direct Arylation of Primary and Secondary sp³ C–H Bonds with Diarylhyperiodonium Salts via Pd Catalysis
  作者：Fei Pan、Peng-Xiang Shen、Li-Sheng Zhang、Xin Wang、Zhang-Jie Shi

  DOI：10.1021/ol402116a

  日期：2013.9.20

  Palladium-catalyzed primary and secondary sp3 C–H bond arylation is reported. The method using diarylhyperiodonium salts as arylation reagents shows good functional group tolerance and proceeds under mild reaction conditions. The KIE experiments show that the C–H bond activation is the rate-determining step.

  据报道钯催化的第一级和第二级sp 3 C–H键芳基化。使用二芳基高碘鎓盐作为芳基化试剂的方法显示出良好的官能团耐受性，并且在温和的反应条件下进行。KIE实验表明，CH键的活化是决定速率的步骤。
• Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling
  作者：Joseph Derosa、Van T. Tran、Mark N. Boulous、Jason S. Chen、Keary M. Engle

  DOI：10.1021/jacs.7b06567

  日期：2017.8.9

  A nickel-catalyzed conjunctive cross-coupling between non-conjugated alkenes, aryl iodides, and alkylzinc reagents is reported. Excellent regiocontrol is achieved utilizing an 8-aminoquinoline directing group that can be readily cleaved to unmask net β,γ-dicarbofunctionalized carboxylic acid products. Under optimized conditions, both terminal and internal alkene substrates provided the corresponding

  报道了非共轭烯烃，芳基碘化物和烷基锌试剂之间镍催化的联合交叉偶联。利用8-氨基喹啉导向基团可实现出色的区域控制，该基团可轻松裂解以揭露净的β，γ-双糖官能化羧酸产物。在优化的条件下，末端和内部烯烃底物均以中等至优异的产率提供了相应的烷基/芳基双官能化产物。本文开发的该方法学代表了涉及C（sp 3）–C（sp 3）还原消除步骤的非共轭​​烯烃的第一个三组分1,2-二糖官能化。
• Redox-Paired Alkene Difunctionalization Enables Skeletally Divergent Synthesis
  作者：Hui-Qi Ni、Malkanthi K. Karunananda、Tian Zeng、Shenghua Yang、Zhen Liu、K.N. Houk、Peng Liu、Keary M. Engle

  DOI：10.1021/jacs.3c03274

  日期：2023.6.7

  underdeveloped approach is designing organic reactions that generate multiple valuable products with different carbogenic skeletons in a single synthetic operation. Taking inspiration from paired electrosynthesis processes that are widely used in commodity chemical production (e.g., conversion of glucose to sorbitol and gluconic acid), we report a palladium-catalyzed reaction that converts a single alkene starting

  多步有机合成能够将简单的化学原料转化为具有特定功能的结构更复杂的产品。目标化合物经过几个步骤形成，在每个步骤中伴随产生副产物，以解释反应的潜在机械特征（例如，氧化还原过程）。为了映射结构-功能关系，通常需要分子库，而这些通常是通过迭代已建立的多步合成序列来制备的。一种不发达的方法是设计有机反应，在一次合成操作中生成具有不同碳骨架的多种有价值的产品。从广泛用于商品化学品生产的成对电合成过程中汲取灵感（例如，将葡萄糖转化为山梨糖醇和葡萄糖酸），我们报告了一种钯催化的反应，该反应通过一系列碳-碳和碳-杂原子键形成事件在一次操作中将单一烯烃起始材料转化为两种骨架不同的产物，该过程由相互氧化和还原引起，我们称之为氧化还原对烯烃双官能化。我们展示了该方法的范围，可以同时获得还原性 1,2-二芳基化和氧化性 [3 + 2]-环化产物，并且我们结合实验技术和密度泛函理论探索了这种独特催化系统的机械细节（干