10-(4-bromophenyl)-9-(2-(4-bromophenylamino)-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-3,4,9,10-tetrahydroacridin-1(2H)-one | 1196957-97-7

• 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: 10-(4-bromophenyl)-9-(2-(4-bromophenylamino)-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-3,4,9,10-tetrahydroacridin-1(2H)-one
• 英文别名: 9-[2-(4-bromophenylamino)-4,4-dimethyl-6-oxocyclohex-1-enyl]-10-(4-bromoophenyl)-3,4-dihydro-3,3-dimethylacridin-1(2H,9H,10H)-one；9-(2-(4-bromophenylamino)-4,4-dimethyl-6-oxocyclohex-1-enyl)-10-(4-bromophenyl)-3,4-dihydro-3,-3-dimethylacridin-1(2H,9H,10H)-one；9-[2-(4-bromoanilino)-4,4-dimethyl-6-oxocyclohexen-1-yl]-10-(4-bromophenyl)-3,3-dimethyl-4,9-dihydro-2H-acridin-1-one
• CAS: 1196957-97-7
• 化学式: C₃₅H₃₄Br₂N₂O₂
• 分子量: 674.475
• InChiKey: MULUKDKJZHLZCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-溴苯胺基)-5,5-二甲基环己-2-烯-1-酮 、 2-碘苯甲醛 在 三乙烯二胺 、 palladium diacetate 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以78%的产率得到10-(4-bromophenyl)-9-(2-(4-bromophenylamino)-4,4-dimethyl-6-oxocyclohex-1-enyl)-3,3-dimethyl-3,4,9,10-tetrahydroacridin-1(2H)-one
  参考文献：
  名称：

  在 Pd(OAc)2/DABCO 催化体系存在下新型、高效、一锅法合成 1,4-二氢喹啉衍生物

  摘要：

  首次发现 Pd(OAc)2/DABCO 催化体系对 C-N 交叉偶联反应非常有效。在这种转化的帮助下，从邻卤苯甲醛和各种 β-烯胺酮合成了各种新的 1,4-二氢喹啉衍生物，产率很高。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  DOI：

  10.1002/ejoc.200900451

文献信息

• Nano-Iron Oxide as a Recyclable Catalyst for Intramolecular CN Cross-Coupling Reactions under Ligand-Free Conditions: One-Pot Synthesis of 1,4-Dihydroquinoline Derivatives
  作者：Xiao-Jin Wu、Ran Jiang、Bing Wu、Xiao-Ming Su、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1002/adsc.200900481

  日期：2009.12

  The ligand-free nanoparticle ferroferric oxide catalytic system has been developed to promote the intramolecular CN cross-coupling reaction. With this protocol, various 1,4-dihydroquinoline derivatives were synthesized from o-halobenzaldehydes and β-enaminones in moderate to good yields.

  已经开发了无配体的纳米颗粒三氧化二铁催化体系，以促进分子内CN交叉偶联反应。利用该方案，从邻卤代苯甲醛和β-烯胺酮以中等至良好的产率合成了各种1,4-二氢喹啉衍生物。
• Synthesis of 1,4-dihydroquinoline derivatives under transition-metal-free conditions and their diverse applications
  作者：Xue-Qiang Chu、You Zi、Hua Meng、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1039/c4ob00475b

  日期：——

  A transition-metal-free process for the synthesis of 1,4-dihydroquinoline derivatives starting from simple enaminones with aldehydes via intermolecular cascade cyclization in a one-pot protocol is developed. This methodology affords a variety of products in moderate to good yields. Particularly, the use of the enaminone fragment in 1,4-dihydroquinoline derivatives 3 as a leaving group for further diverse applications with C-nucleophiles is proved to be feasible.

  以简单的烯氨酮和醛为起点，通过分子间级联环化，以一锅协议合成 1,4-二氢喹啉衍生物的无过渡金属工艺被开发出来。该方法能以中等至较高的产率获得多种产品。特别是，将 1,4-二氢喹啉衍生物 3 中的烯丙酮片段作为离去基团与 C-亲核物一起用于进一步的多种应用被证明是可行的。
• A Novel, Highly Efficient, One-Pot Synthesis of 1,4-Dihydroquinoline Derivatives in the Presence of a Pd(OAc)₂/DABCO Catalytic System
  作者：Xiao-Jin Wu、Xiao-Ping Xu、Xiao-Ming Su、Gang Chen、Yong Zhang、Shun-Jun Ji

  DOI：10.1002/ejoc.200900451

  日期：2009.10

  The Pd(OAc)2/DABCO catalytic system was first found to be highly efficient for C–N cross-coupling reactions. With the aid of this transformation, a variety of new 1,4-dihydroquinoline derivatives were synthesized from o-halobenzaldehydes and various β-enaminones in good to excellent yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  首次发现 Pd(OAc)2/DABCO 催化体系对 C-N 交叉偶联反应非常有效。在这种转化的帮助下，从邻卤苯甲醛和各种 β-烯胺酮合成了各种新的 1,4-二氢喹啉衍生物，产率很高。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)