3-cyclohexyl-N-(quinolin-8-yl)propanamide | 1090519-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-cyclohexyl-N-(quinolin-8-yl)propanamide
• 英文别名: 3-cyclohexyl-N-quinolin-8-ylpropanamide
• CAS: 1090519-99-5
• 化学式: C₁₈H₂₂N₂O
• 分子量: 282.385
• InChiKey: CDTFWVRNJGJUNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyclohexyl-N-(quinolin-8-yl)propanamide 在 2,3,4,5,6-五氟碘苯 、 silver(I) acetate 、 palladium diacetate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.5h， 以83%的产率得到1-(8-quinolinyl)-4-cyclohexylazetidinone
  参考文献：
  名称：

  钯催化羧酰胺未活化的C（sp 3）–H键的分子内胺化立体选择性合成二氮杂双环β-内酰胺

  摘要：

  描述了一种有效的C（sp 3）-H键活化和通过钯催化在羧酰胺的β位上制备β-内酰胺的分子内胺化反应。对底物范围的研究表明，当前的反应条件有利于β-亚甲基的活化。通过手性脯氨酸和哌啶衍生物的关键步骤，开发了用于制备各种二氮杂双环β-内酰胺化合物的短序列。

  DOI：

  10.1021/acs.joc.5b02532

文献信息

• Efficient Palladium-Catalyzed C–H Fluorination of C(sp3)–H Bonds: Synthesis of β-Fluorinated Carboxylic Acids
  作者：Qihua Zhu、Dezhong Ji、Tingting Liang、Xueyan Wang、Yungen Xu

  DOI：10.1021/acs.orglett.5b01774

  日期：2015.8.7

  A novel and facile process for direct fluorination of unactivated C(sp3)–H bonds at the β position of carboxylic acids was accomplished by a palladium(II)-catalyzed C–H activation. The addition of Ag2O and pivalic acid was found to be crucial for the success of this transformation. This reaction provides a versatile strategy for the synthesis of β-fluorinated carboxylic acids.

  通过钯（II）催化的C–H活化作用，可以实现一种新颖且简便的方法，可直接氟化羧酸β位上未活化的C（sp3）–H键。发现Ag 2 O和新戊酸的添加对于该转化的成功至关重要。该反应为合成β-氟化羧酸提供了一种通用的策略。
• N-喹啉基取代的β-内酰胺类化合物及其药物 组合物和合成方法与应用
  申请人：中国科学院昆明植物研究所

  公开号：CN103524486B

  公开（公告）日：2016-03-02

  通式（I）所示的N-喹啉基取代的β-内酰胺化合物，式中，R1、R2是相互独立的H或C1-12的直链或支链的烃基、芳基、烷氧基、酰氧基或氨基；R3是H或C1-25的直链或支链的烃基、芳基，或者与R1或R2形成取代或未取代的5～8元环，所述的5～8元环含或不含杂原子，所述的杂原子可以是N、O、S；R4、R5是相互独立的H或C1-12的直链或支链的烃基、芳基、烷氧基、酰氧基或氨基,硝基、磺酸基和卤素，所述的卤素是F、Cl、Br、I。本发明还提供这些化合物的合成方法，含有所述化合物的药物组合物，及所述化合物在β-内酰胺酶抑制剂的药物制备中的应用。
• Palladium-Catalyzed Aerobic α,β-Dehydrogenation of Aliphatic Amides
  作者：Meledath Sudhakaran Keerthana、Masilamani Jeganmohan

  DOI：10.1021/acs.joc.2c00226

  日期：2022.4.1

  A Pd(II)-catalyzed α,β-dehydrogenation of substituted aliphatic amides assisted by a reusable bis-chelating 8-aminoquinoline ligand is demonstrated. Broad spectra of β-substituted including olefin-substituted aliphatic amides are well tolerated. The present protocol efficiently dehydrogenates the less acidic aliphatic amides via the chelation-assisted β-C–H bond activation and replaces the traditional

  证明了由可重复使用的双螯合 8-氨基喹啉配体辅助的 Pd(II) 催化的取代脂肪族酰胺的 α,β-脱氢。β-取代的广谱包括烯烃取代的脂肪族酰胺具有良好的耐受性。本协议通过螯合辅助的 β-C-H 键活化有效地使酸性较低的脂肪族酰胺脱氢，并取代了传统的基于烯醇化物的策略。
• Palladium-Catalyzed Cs₂CO₃-Promoted Arylation of Unactivated C(sp³)–H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation
  作者：Quan Gou、Zhao-Fu Zhang、Zhi-Cheng Liu、Jun Qin

  DOI：10.1021/acs.joc.5b00111

  日期：2015.3.20

  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.
• Palladium-Catalyzed Unactivated C(sp³)–H Bond Activation and Intramolecular Amination of Carboxamides: A New Approach to β-Lactams
  作者：Wen-Wu Sun、Pei Cao、Ren-Qiang Mei、Yue Li、Yuan-Liang Ma、Bin Wu

  DOI：10.1021/ol403364k

  日期：2014.1.17

  An efficient method to synthesize the beta-lactams with high regioselectivity via Pd-catalyzed C(sp(3))-H bond activation and intramolecular arnination of simple and readily available aminoquinoline carboxamides was demonstrated. C6F5I plays a significant role in the formation of the C-N bond of the four-membered ring beta-lactams. High yield along with wide substrate scope and functional group tolerance makes this reaction applicable to build natural-product-derived beta-lactams. This method has been applied to the efficient synthesis of the beta-lactamase inhibitor MK-8712.