N,N,2-triethyl-6-formylbenzamide | 721947-02-0

• 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,2-triethyl-6-formylbenzamide
• CAS: 721947-02-0
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: JFWKWBOCUCCRJO-UHFFFAOYSA-N

物化性质

• 沸点：
  403.5±45.0 °C(Predicted)
• 密度：
  1.049±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  麻黄碱 、 N,N,2-triethyl-6-formylbenzamide 以 甲苯 为溶剂， 反应 16.0h， 以87%的产率得到(P,2'S,4'S,5'R)-N,N-diethyl-2-(3,4-dimehyl-5-phenyl-1,3-oxazolan-2-yl)-6-ethylbenzamide
  参考文献：
  名称：

  使用脯氨酸衍生的咪唑啉和麻黄碱衍生的恶唑烷类化合物动态拆分阻转异构酰胺

  摘要：

  阻转异构的叔2-甲酰基萘酰胺或2-甲酰基苯甲酰胺与一些手性二胺和氨基醇的缩合通过动态拆分过程导致带有手性咪唑烷或恶唑烷的叔酰胺的单一阻转异构体。新杂环的水解与起始醛的动态热力学拆分竞争，并且快速还原可分离出对映异构体富集形式的带有2-羟甲基取代基的阻转异构酰胺。提供了反应在热力学控制下的证据。

  DOI：

  10.1016/j.tet.2004.01.101
• 作为产物：
  描述：

  N,N-二乙基苯甲酰胺 在 四丁基氟化铵 、 仲丁基锂 作用下， 生成 N,N,2-triethyl-6-formylbenzamide
  参考文献：
  名称：

  (−)-Ephedrine as an auxiliary for the asymmetric synthesis of atropisomeric amides by dynamic resolution under thermodynamic control

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)00416-6

文献信息

• DERIVATIVES OF UNCIALAMYCIN, METHODS OF SYNTHESIS AND THEIR USE AS ANTITUMOR AGENTS
  申请人：WILLIAM MARSH RICE UNIVERSITY

  公开号：US20160185791A1

  公开（公告）日：2016-06-30

  In one aspect, the present disclosure provides new analogs of uncialamycin of formulae (I) and (II). The present disclosure also provides novel synthetic pathways to obtaining uncialamycin and analogs thereof. Additionally, the present disclosure also describes methods of use of uncialamycin and analogs thereof. In another aspect, the present disclosure provides antibody-drug conjugates comprising the compounds of formulae (I) and (II).

  在某个方面，本公开提供了式（I）和（II）的新的uncialamycin类似物。本公开还提供了获得uncialamycin及其类似物的新型合成途径。此外，本公开还描述了uncialamycin及其类似物的使用方法。在另一方面，本公开提供了包含式（I）和（II）化合物的抗体药物偶联物。
• US9777013B2
  申请人：——

  公开号：US9777013B2

  公开（公告）日：2017-10-03
• Dynamic resolution of atropisomeric amides using proline-derived imidazolines and ephedrine-derived oxazolidines
  作者：Jonathan Clayden、Lai Wah Lai、Madeleine Helliwell

  DOI：10.1016/j.tet.2004.01.101

  日期：2004.5

  some chiral diamines and amino alcohols leads, via a dynamic resolution process, to single atropisomers of tertiary amides bearing chiral imidazolidines or oxazolidines. Hydrolysis of the new heterocycle competes a dynamic thermodynamic resolution of the starting aldehyde, and rapid reduction allows the isolation of atropisomeric amides bearing 2-hydroxymethyl substituents in enantiomerically enriched

  阻转异构的叔2-甲酰基萘酰胺或2-甲酰基苯甲酰胺与一些手性二胺和氨基醇的缩合通过动态拆分过程导致带有手性咪唑烷或恶唑烷的叔酰胺的单一阻转异构体。新杂环的水解与起始醛的动态热力学拆分竞争，并且快速还原可分离出对映异构体富集形式的带有2-羟甲基取代基的阻转异构酰胺。提供了反应在热力学控制下的证据。
• (−)-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.