N-(2,4-dimethoxybenzyl)-N-ethylethanamine | 898222-57-6

• 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-(2,4-dimethoxybenzyl)-N-ethylethanamine
• 英文别名: N-[(2,4-dimethoxyphenyl)methyl]-N-ethylethanamine
• CAS: 898222-57-6
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: ACLSKGLCNJYGTP-UHFFFAOYSA-N

物化性质

• 沸点：
  291.0±25.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,4-dimethoxybenzyl)-N-ethylethanamine 、 乙酸酐 在 三氟化硼-二甲醚络合物 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以52%的产率得到1-(2-hydroxy-4-methoxy-5-methylphenyl)ethanone
  参考文献：
  名称：

  Antiproliferative activity of chalcones with basic functionalities

  摘要：

  A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection methods (PCA/PLS) and multiple linear regression. Polar volume, hydrogen bonding features, HOMO energies, and charge on the carbon were found to be important factors. A basic group on either ring A or B of the chalcone led to a favourable increase in polar Volume, but when present on ring B, it increased HOMO energies and decreased the positive charge on the carbon, both of which led to lower activity. Several examples showed that final activity of the chalcone was influenced by compensatory interactions among these parameters. In general, a single basic group on ring A was associated with good activity. A notable exception was compound 1-123 which had basic groups on both rings A and B but Still maintained a good activity profile with IC50 < 10 PM and selectivity ratios >2.5. There was some evidence to show that structural differences in chalcones influenced not only activity but mechanism of action. Compounds 6-130 and 7-140 which had basic groups on ring A interfered with cell cycle progression, but the dibasic chalcone 1-123 had no effect. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.042
• 作为产物：
  描述：

  N,N-diethyl-2,4-dimethoxybenzamide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 N-(2,4-dimethoxybenzyl)-N-ethylethanamine
  参考文献：
  名称：

  Antiproliferative activity of chalcones with basic functionalities

  摘要：

  A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection methods (PCA/PLS) and multiple linear regression. Polar volume, hydrogen bonding features, HOMO energies, and charge on the carbon were found to be important factors. A basic group on either ring A or B of the chalcone led to a favourable increase in polar Volume, but when present on ring B, it increased HOMO energies and decreased the positive charge on the carbon, both of which led to lower activity. Several examples showed that final activity of the chalcone was influenced by compensatory interactions among these parameters. In general, a single basic group on ring A was associated with good activity. A notable exception was compound 1-123 which had basic groups on both rings A and B but Still maintained a good activity profile with IC50 < 10 PM and selectivity ratios >2.5. There was some evidence to show that structural differences in chalcones influenced not only activity but mechanism of action. Compounds 6-130 and 7-140 which had basic groups on ring A interfered with cell cycle progression, but the dibasic chalcone 1-123 had no effect. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.042

文献信息

• Reductive Amination of Aldehydes Using Aminoboranes as Iminium Ion Generators
  作者：Michinori Suginome、Yusuke Tanaka、Tomoaki Hasui

  DOI：10.1055/s-2006-939070

  日期：——

  2-Dialkylamino-4H-1,3,2-benzodioxaborins, salicyl alcohol derived aminoboranes, serve as efficient and mild iminium ion generators in the reductive amination of aldehydes with NaBH4. Using a diisopropylamino derivative, a variety of amines including secondary and primary amines, and ammonia can participate to the reductive amination in aprotic organic solvents without the use of acidic promoters.

  2-二烷基氨基-4H-1,3,2-苯并二氧硼烷和基于水杨醇的氨基硼烷在与NaBH4的还原胺化反应中，作为高效且温和的亚胺离子生成剂。使用二异丙基氨基衍生物，二级和初级胺以及氨可以在无质子有机溶剂中参与还原胺化，而无需使用酸性促进剂。
• Antiproliferative activity of chalcones with basic functionalities
  作者：Xiaoling Liu、Mei-Lin Go

  DOI：10.1016/j.bmc.2007.07.042

  日期：2007.11

  A library of chalcones with different basic groups were synthesized and evaluated for antiproliferative activities against the human breast cancer (MCF 7) and colon cancer (HCT 116) cell lines. Structure-activity relationships were analyzed by projection methods (PCA/PLS) and multiple linear regression. Polar volume, hydrogen bonding features, HOMO energies, and charge on the carbon were found to be important factors. A basic group on either ring A or B of the chalcone led to a favourable increase in polar Volume, but when present on ring B, it increased HOMO energies and decreased the positive charge on the carbon, both of which led to lower activity. Several examples showed that final activity of the chalcone was influenced by compensatory interactions among these parameters. In general, a single basic group on ring A was associated with good activity. A notable exception was compound 1-123 which had basic groups on both rings A and B but Still maintained a good activity profile with IC50 < 10 PM and selectivity ratios >2.5. There was some evidence to show that structural differences in chalcones influenced not only activity but mechanism of action. Compounds 6-130 and 7-140 which had basic groups on ring A interfered with cell cycle progression, but the dibasic chalcone 1-123 had no effect. (C) 2007 Elsevier Ltd. All rights reserved.