N,N-diisopropyl-2-ethyl-6-formylbenzamide | 227201-73-2

• 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-diisopropyl-2-ethyl-6-formylbenzamide
• 英文别名: 2-ethyl-6-formyl-N,N-di(propan-2-yl)benzamide
• CAS: 227201-73-2
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: MKBLIQIWNOMXNF-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  416.2±45.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 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：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diisopropyl-2-ethyl-6-formylbenzamide 在 sodium tetrahydroborate 、 硼烷 、 仲丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 28.67h， 生成 (+/-)-N,N-diisopropyl-2-[(1S',2S')-2-{(diisopropylamino)carbonyl]-3-ethylphenyl}-1-methyl-2-(dimethylaminoborane)ethyl-1-naphthamide
  参考文献：
  名称：

  Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2′-dicarboxamides

  摘要：

  将侧向锂化的叔芳香酰胺添加到苯亚甲基中可以控制与苯亚甲基芳环相邻的新立体中心的形成。利用这样的氨基取代的立体中心本身可以控制酰胺的构象的事实，利用酰胺基取代的苯甲醛亚胺，我们发现可以通过这种介入的立体中心将立体化学从一种酰胺传递到另一种酰胺。通过该方法制备了一组带有一个或两个立构轴的二氢芪-2,2-二甲酰胺衍生物，这证明了使用组合动力学和热力学控制来传递立体化学信息。

  DOI：

  10.1039/b514561a
• 作为产物：
  描述：

  2-formyl-N,N-diisopropylbenzamide 在 叔丁基锂 作用下， 生成 N,N-diisopropyl-2-ethyl-6-formylbenzamide
  参考文献：
  名称：

  Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines

  摘要：

  Atroposelective addition of axially chiral laterally lithiated 2-alkyl-1-naphthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after equilibration of the new stereogenic axis to its more stable conformation, to single atropisomeric diastereoisomers of diamides bearing remotely related stereogenic axes separated by one or two stereogenic centres. The newly created MeNH-bearing stereogenic centre "relays" stereochemical information from the first axis to the second. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00520-1

文献信息

• (−)-Ephedrine as an auxiliary for the asymmetric synthesis of atropisomeric amides by dynamic resolution under thermodynamic control
  作者：Jonathan Clayden、Lai Wah Lai

  DOI：10.1016/s0040-4039(01)00416-6

  日期：2001.4

  N,N-Dialkyl-2-formylbenzamides and N,N-dialkyl-2-formyl-1-naphthamides condense with (-)-ephedrine in refluxing toluene to give oxazolidines both as single diastereoisomers with respect to the new stereogenic centre and as single conformers with respect to the slowly-rotating Ar-CONR2 bond. In the naphthamide series, removal of the ephedrine auxiliary by hydrolysis returns the starting aldehyde (isolated by reduction to the more stable alcohol) in enantiomerically enriched form (up to 94% ee). Overall, the two-step sequence amounts to a dynamic resolution under thermodynamic control. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines
  作者：Jonathan Clayden、Neil Westlund、Francis X. Wilson

  DOI：10.1016/s0040-4039(99)00520-1

  日期：1999.4

  Atroposelective addition of axially chiral laterally lithiated 2-alkyl-1-naphthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after equilibration of the new stereogenic axis to its more stable conformation, to single atropisomeric diastereoisomers of diamides bearing remotely related stereogenic axes separated by one or two stereogenic centres. The newly created MeNH-bearing stereogenic centre "relays" stereochemical information from the first axis to the second. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Diastereoselective synthesis of atropisomers containing two non-biaryl stereogenic axes: stereochemical relay through stereogenic centres in dihydrostilbene-2,2′-dicarboxamides
  作者：Jonathan Clayden、Neil Westlund、Christopher S. Frampton、Madeleine Helliwell

  DOI：10.1039/b514561a

  日期：——

  Addition of laterally lithiated tertiary aromatic amides to benzaldimines controls the formation of a new stereogenic centre adjacent to the benzaldimine aromatic ring. Drawing on the fact that such amino-substituted stereogenic centres may themselves control the conformation of amides, with amido-substituted benzaldimines we found it becomes possible to relay stereochemistry from one amide to another via this intervening stereogenic centre. A group of dihydrostilbene-2,2′-dicarboxamide derivatives bearing one or two stereogenic axes are made by this method, which demonstrates the use of combined kinetic and thermodynamic control for the relay of stereochemical information.

  将侧向锂化的叔芳香酰胺添加到苯亚甲基中可以控制与苯亚甲基芳环相邻的新立体中心的形成。利用这样的氨基取代的立体中心本身可以控制酰胺的构象的事实，利用酰胺基取代的苯甲醛亚胺，我们发现可以通过这种介入的立体中心将立体化学从一种酰胺传递到另一种酰胺。通过该方法制备了一组带有一个或两个立构轴的二氢芪-2,2-二甲酰胺衍生物，这证明了使用组合动力学和热力学控制来传递立体化学信息。