2-formyl-6-dimethylamino-N,N-diisopropylbenzamide | 464914-38-3

• 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: 2-formyl-6-dimethylamino-N,N-diisopropylbenzamide
• 英文别名: 2-(dimethylamino)-6-formyl-N,N-di(propan-2-yl)benzamide
• CAS: 464914-38-3
• 化学式: C₁₆H₂₄N₂O₂
• 分子量: 276.379
• InChiKey: WBJRXZWZQWPSTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  磷酰基乙酸三乙酯 、 2-formyl-6-dimethylamino-N,N-diisopropylbenzamide 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 14.0h， 以94%的产率得到(E)-3-(2-Diisopropylcarbamoyl-3-dimethylamino-phenyl)-acrylic acid ethyl ester
  参考文献：
  名称：

  Kinetic Resolution of Atropisomeric Amides

  摘要：

  We have demonstrated the feasibility of the kinetic resolution of atropisomeric amides using the commercially avaliable AD-mix. To our knowledge, this methodology represents the first catalytic kinetic resolution of such compounds. Relative rates of up to 32 have been found for the kinetic resolution processes. We have also determined the barriers to rotation and half-lives of some of these amides. The half-lives range from 7 to 135 h at room temperature.

  DOI：

  10.1021/ja026436r
• 作为产物：
  描述：

  2-dimethylamino-N,N-diisopropylbenzamide 、 N,N-二甲基甲酰胺 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 乙醚 为溶剂， 以95%的产率得到2-formyl-6-dimethylamino-N,N-diisopropylbenzamide
  参考文献：
  名称：

  Kinetic Resolution of Atropisomeric Amides

  摘要：

  We have demonstrated the feasibility of the kinetic resolution of atropisomeric amides using the commercially avaliable AD-mix. To our knowledge, this methodology represents the first catalytic kinetic resolution of such compounds. Relative rates of up to 32 have been found for the kinetic resolution processes. We have also determined the barriers to rotation and half-lives of some of these amides. The half-lives range from 7 to 135 h at room temperature.

  DOI：

  10.1021/ja026436r

文献信息

• Rapid, highly diastereoselective addition of dialkylzinc reagents to atropisomeric 2-formyl arylamides
  作者：Ciril Jimeno、Ramon Rios、Patrick J. Carroll、Patrick J. Walsh

  DOI：10.1016/j.tet.2003.12.071

  日期：2004.5

  dialkylzinc reagents add to atropisomeric 2-formyl arylamides many times faster than they react with other substituted benzaldehyde derivatives. Additionally, with diethylzinc the products were formed with very high diastereoselectivity, affording the syn product (d.r. greater than 95:5), except in one case where epimerization of the product is rapid. In contrast, Grignard and trialkylaluminum reagents afforded

  我们已经观察到二烷基锌试剂加到阻转异构体2-甲酰基芳基酰胺中的速度比它们与其他取代的苯甲醛衍生物的反应快许多倍。另外，用二乙基锌形成的产物具有非常高的非对映选择性，提供了顺式产物（dr大于95：5），除非在一种情况下产物的差向异构化迅速。相比之下，格氏三烷基铝和试剂提供的反异构体，与减少的立体选择性和形成的还原产物。
• Dynamic Kinetic Resolution of Atropisomeric Amides
  作者：Vincent Chan、Jeung Gon Kim、Ciril Jimeno、Patrick J. Carroll、Patrick J. Walsh

  DOI：10.1021/ol0492952

  日期：2004.6.1

  Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.01.
• Kinetic Resolution of Atropisomeric Amides
  作者：Ramon Rios、Ciril Jimeno、Patrick J. Carroll、Patrick J. Walsh

  DOI：10.1021/ja026436r

  日期：2002.9.1

  We have demonstrated the feasibility of the kinetic resolution of atropisomeric amides using the commercially avaliable AD-mix. To our knowledge, this methodology represents the first catalytic kinetic resolution of such compounds. Relative rates of up to 32 have been found for the kinetic resolution processes. We have also determined the barriers to rotation and half-lives of some of these amides. The half-lives range from 7 to 135 h at room temperature.