N,N-diethyl-4-octylbenzamide | 1173372-07-0

• 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,N-diethyl-4-octylbenzamide
• CAS: 1173372-07-0
• 化学式: C₁₉H₃₁NO
• 分子量: 289.461
• InChiKey: RFZNXNVPXPUOEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-(dimethylamino)-N,N-diethylbenzamide 在 iron(III)-acetylacetonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N,N-diethyl-4-octylbenzamide
  参考文献：
  名称：

  Iron-catalyzed cross-coupling of aryltrimethylammonium triflates and alkyl Grignard reagents

  摘要：

  Fe(acac)(3) effectively catalyzes reaction of aryltrimethylammonium triflates with beta-hydrogen-containing primary or secondary alkyl Grignard reagents in a mixed solvent of THF and NMP at room temperature. A series of functional groups are tolerated under the reaction conditions. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.039

文献信息

• <i>para</i>-Selective Alkylation of Benzamides and Aromatic Ketones by Cooperative Nickel/Aluminum Catalysis
  作者：Shogo Okumura、Shuwei Tang、Teruhiko Saito、Kazuhiko Semba、Shigeyoshi Sakaki、Yoshiaki Nakao

  DOI：10.1021/jacs.6b08767

  日期：2016.11.9

  We report a method that ensures the selective alkylation of benzamides and aromatic ketones at the para-position via cooperative nickel/aluminum catalysis. Using a bulky catalyst/cocatalyst system allows reactions between benzamides and alkenes to afford the corresponding para-alkylated products. The origin of the high para-selectivity has also been investigated by density functional theory calculations

  我们报告了一种通过镍/铝协同催化确保苯甲酰胺和芳族酮在对位选择性烷基化的方法。使用庞大的催化剂/助催化剂体系允许苯甲酰胺和烯烃之间的反应得到相应的对位烷基化产物。还通过密度泛函理论计算研究了高对位选择性的起源。
• Functional Group Tolerant Kumada−Corriu−Tamao Coupling of Nonactivated Alkyl Halides with Aryl and Heteroaryl Nucleophiles: Catalysis by a Nickel Pincer Complex Permits the Coupling of Functionalized Grignard Reagents
  作者：Oleg Vechorkin、Valérie Proust、Xile Hu

  DOI：10.1021/ja9027378

  日期：2009.7.22

  A nickel(II) pincer complex [((Me)NN(2))NiCl] (1) catalyzes Kumada-Corriu-Tamao cross coupling of nonactivated alkyl halides with aryl and heteroaryl Grignard reagents. The coupling of octyl bromide with phenylmagnesium chloride was used as a test reaction. Using 3 mol % of 1 as the precatalyst and THF as the solvent, and in the presence of a catalytic amount of TMEDA, the coupling product was obtained

  镍 (II) 钳形复合物 [((Me)NN(2))NiCl] (1) 催化未活化的卤代烷与芳基和杂芳基格氏试剂的 Kumada-Corriu-Tamao 交叉偶联。辛基溴与苯基氯化镁的偶联用作测试反应。以3mol%的1为预催化剂，THF为溶剂，在催化量的TMEDA存在下，以高收率得到偶联产物。该反应条件可用于其他伯和仲烷基溴化物和碘化物的交叉偶联。该偶联可耐受范围广泛的官能团。因此，将含有酯、酰胺、醚、硫醚、醇、吡咯、吲哚、呋喃、腈、共轭烯酮和芳基卤部分的卤代烷进行偶联，以得到高分离产率的产品，其中这些单元保持完整。对于含酯底物的偶联，O-TMEDA 是比 TMEDA 更好的添加剂。该反应方案被证明对于 Knochel 型官能化格氏试剂的偶联是有效的。因此，含有缺电子和/或敏感酯、腈、酰胺和 CF(3) 取代基的芳基格氏试剂可以成功地偶联到未活化和功能化的烷基碘。该催化还可以有效地将烷基碘
• Iron-catalyzed cross-coupling of aryltrimethylammonium triflates and alkyl Grignard reagents
  作者：Wang-Jun Guo、Zhong-Xia Wang

  DOI：10.1016/j.tet.2013.09.039

  日期：2013.11

  Fe(acac)(3) effectively catalyzes reaction of aryltrimethylammonium triflates with beta-hydrogen-containing primary or secondary alkyl Grignard reagents in a mixed solvent of THF and NMP at room temperature. A series of functional groups are tolerated under the reaction conditions. (c) 2013 Elsevier Ltd. All rights reserved.