4-chloro-N-(tricyclo[3.3.1.1^3,7]dec-1-yl)benzamide | 56911-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-chloro-N-(tricyclo[3.3.1.1^3,7]dec-1-yl)benzamide
• 英文别名: 4-Chlorbenzoesaeure-amid；N-(1-adamantyl)-4-chlorobenzamide
• CAS: 56911-80-9
• 化学式: C₁₇H₂₀ClNO
• 分子量: 289.805
• InChiKey: MJGIEMQZMGCJSY-UHFFFAOYSA-N

物化性质

• 沸点：
  448.8±28.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  溴苯 、 4-chloro-N-(tricyclo[3.3.1.1^3,7]dec-1-yl)benzamide 在 silver(I) acetate 、 palladium diacetate 作用下， 反应 22.0h， 以47%的产率得到N-adamantyl-4-chloro-2-phenylbenzamide
  参考文献：
  名称：

  Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles

  摘要：

  Diverse libraries of biaryl-amides bearing N-t-butyl and N-adamantyl groups were synthesized in two steps by the Ritter reaction of aryl-nitriles, using tBuOH and AdaOH as carbocation precursors, and employing [BMIM(SO3H)][OTf] (neat or with [BMIM][PF6] as co-solvent) or tetramethyl guanidinium-ILs [TMG][X] (X = CF3COO, EtOSO3) as dual catalyst/solvent, followed by a Pd-catalyzed directed regioselective ortho - C - H arylation of the Ritter amides with Ar-X (X = I, Cl). The feasibility to perform the two-steps in sequence is also demonstrated, and potential for recycling/reuse of the ILs is also shown. Preference for [Pd] coordination to the amide carbonyl versus amide nitrogen is borne out by DFT computations. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.152553
• 作为产物：
  描述：

  金刚烷 、 4-Chloro-N-(3-oxo-3H-1λ³-benzo[d][1,2]iodoxol-1-yl)-benzamide 在 过氧化苯甲酰 作用下， 以 氯苯 为溶剂， 反应 4.0h， 以58%的产率得到4-chloro-N-(tricyclo[3.3.1.1^3,7]dec-1-yl)benzamide
  参考文献：
  名称：

  1-Amido-3-(1H)-1,2-benziodoxoles: Stable amidoiodanes and reagents for direct amidation of organic substrates

  摘要：

  Amidobenziodoxoles 2 can be prepared from benziodoxole 1, trimethylsilyltriflate and the appropriate amides in the form of stable, microcrystalline compounds. Amidobenziodoxoles 2 react with adamantane 3 or N,N-dimethylarylamines 5 to afford the corresponding products of amidation, 4 and 6. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02245-9

文献信息

• Rh(<scp>iii</scp>)-catalyzed direct C–H/C–H cross-coupling of quinones with arenes assisted by a directing group: identification of carbazole quinones as GSKβ inhibitors
  作者：Youngtaek Moon、Yujeong Jeong、Daehyuk Kook、Sungwoo Hong

  DOI：10.1039/c4ob02624a

  日期：——

  Rh-catalyzed direct cross-coupling of various (hetero)arenes with quinones is developed. This protocol is effective for a broad range of substrates and a wide range of directing groups.

  铑催化的直接交叉偶联反应可将各种(杂)芳烃与醌进行偶联。该方案适用于广泛的底物和多种取向基团。
• CuI nanoparticles as recyclable heterogeneous catalysts for C–N bond formation reactions
  作者：Manoranjan Kumar、Vinod Bhatt、Onkar S. Nayal、Sushila Sharma、Vishal Kumar、Maheshwar S. Thakur、Neeraj Kumar、Rajaram Bal、Bikram Singh、Upendra Sharma

  DOI：10.1039/c7cy00832e

  日期：——

  resulting NPs were CuI instead of Cu. The TEM images of CuI exhibited the size of monodispersed spherical NPs in the range of 4 ± 2 nm. These generated NPs can be used as versatile heterogeneous catalysts for important organic transformations. As a proof of concept, CuI NPs were successfully applied as heterogeneous catalysts for the synthesis of secondary amines, amides and triazoles. CuI NPs can be easily

  本文中，首次报道了碘化铜纳米颗粒（NPs）用于羰基化合物的还原胺化。通过TEM，EDX，XRD和XPS分析对生成的NP进行表征。XRD图谱，XPS和EDX分析证实，所得的NP是CuI而不是Cu。CuI的TEM图像显示单分散球形NP的大小在4±2 nm范围内。这些生成的NP可用作重要有机转化的通用多相催化剂。作为概念证明，CuI NPs已成功地用作合成仲胺，酰胺和三唑的非均相催化剂。CuI NP可以轻松回收和循环使用多达六次。
• Nafion®-catalyzed microwave-assisted Ritter reaction: an atom-economic solvent-free synthesis of amides
  作者：Vivek Polshettiwar、Rajender S. Varma

  DOI：10.1016/j.tetlet.2008.02.009

  日期：2008.4

  An atom-economic solvent-free synthesis of amides by the Ritter reaction of alcohols and nitriles under microwave irradiation is reported. This green protocol is catalyzed by solid-supported Nafion®NR50 with improved efficiency and reduced waste production.

  报道了在微波辐射下通过醇和腈的Ritter反应的无原子经济的无溶剂合成酰胺。此绿色协议由固体负载的Nafion催化® NR50具有提高的效率和降低的生产废物。
• Synthesis and Biological Evaluation of a Library of Sulfonamide Analogs of Memantine to Target Glioblastoma
  作者：John E. Philo、Jenna D. Caudle、Reema N. Moussa、Patrick M. Kampmeyer、Tasfia R. Hasin、David K. Seo、Robert J. Sheaff、Angus A. Lamar

  DOI：10.1002/cmdc.202300134

  日期：2023.8.15

  A library of 34 sulfonamide analogs of memantine has been synthesized. The in vitro activity of the compounds was investigated resulting in 5 strong hits, and a molecular docking study was conducted on the compounds identified as hits. The synthesis and in vitro evaluation of 14 additional analogs has validated the importance of the sulfonamide unit.

  已合成了 34 种美金刚磺酰胺类似物的文库。研究了化合物的体外活性，产生了 5 个强命中，并对确定为命中的化合物进行了分子对接研究。14 种其他类似物的合成和体外评估验证了磺酰胺单元的重要性。
• Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles
  作者：Suraj M. Sutar、Hemantkumar M. Savanur、Rajesh G. Kalkhambkar、Gabriela L. Borosky、Gopalakrishnan Aridoss、Kenneth K. Laali

  DOI：10.1016/j.tetlet.2020.152553

  日期：2020.12

  Diverse libraries of biaryl-amides bearing N-t-butyl and N-adamantyl groups were synthesized in two steps by the Ritter reaction of aryl-nitriles, using tBuOH and AdaOH as carbocation precursors, and employing [BMIM(SO3H)][OTf] (neat or with [BMIM][PF6] as co-solvent) or tetramethyl guanidinium-ILs [TMG][X] (X = CF3COO, EtOSO3) as dual catalyst/solvent, followed by a Pd-catalyzed directed regioselective ortho - C - H arylation of the Ritter amides with Ar-X (X = I, Cl). The feasibility to perform the two-steps in sequence is also demonstrated, and potential for recycling/reuse of the ILs is also shown. Preference for [Pd] coordination to the amide carbonyl versus amide nitrogen is borne out by DFT computations. (C) 2020 Elsevier Ltd. All rights reserved.