N-(1-adamantyl)-3-bromobenzamide | 304663-23-8

• 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: N-(1-adamantyl)-3-bromobenzamide
• CAS: 304663-23-8
• 化学式: C₁₇H₂₀BrNO
• 分子量: 334.256
• InChiKey: RWPPKMZNZCYJBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：

  N-(1-adamantyl)-3-bromobenzamide 、 对苯醌 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver(I) acetate 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以92%的产率得到N-(adamantan-1-yl)-4-bromo-2',5'-dioxo-2',5'-dihydro-[1,1'-biphenyl]-2-carboxamide
  参考文献：
  名称：

  Rh(iii)-catalyzed direct C–H/C–H cross-coupling of quinones with arenes assisted by a directing group: identification of carbazole quinones as GSKβ inhibitors

  摘要：

  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。

  DOI：

  10.1039/c4ob02624a
• 作为产物：
  描述：

  间溴苯甲腈 、 1-金刚烷醇 在 水 作用下， 反应 18.0h， 以84%的产率得到N-(1-adamantyl)-3-bromobenzamide
  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

文献信息

• Rhodanine-Based Tau Aggregation Inhibitors in Cell Models of Tauopathy
  作者：Bruno Bulic、Marcus Pickhardt、Inna Khlistunova、Jacek Biernat、Eva-Maria Mandelkow、Eckhard Mandelkow、Herbert Waldmann

  DOI：10.1002/anie.200704051

  日期：2007.12.10
• 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。
• 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.