N-(3,4-dimethoxybenzylidene)-2-phenylethanamine | 3241-17-6

• 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-(3,4-dimethoxybenzylidene)-2-phenylethanamine
• 英文别名: N-(β-Phenyl-ethyl)-3,4-dimethoxy-benzaldimin；N-Veratryliden-2-phenethyl-amin；(3,4-dimethoxy-benzylidene)-phenethyl-amine；phenethyl-veratryliden-amine；Veratrumaldehyd-phenaethylimin；Phenaethyl-veratryliden-amin；N-(3,4-dimethoxybenzylidene)phenethylamine；1-(3,4-dimethoxyphenyl)-N-(2-phenylethyl)methanimine
• CAS: 3241-17-6
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: PJXHIHADCAEOKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  401.3±45.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxybenzylidene)-2-phenylethanamine 在 sodium tetrahydroborate 、 盐酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 N-(Phenaethyl)-3,4-dimethoxy-benzyl-amin*HCl
  参考文献：
  名称：

  Synthesis and structure–activity relationship of N-(2-arylethyl) isoquinoline derivatives as human scavenger receptor CD36 antagonists

  摘要：

  By using human scavenger receptor CD36 as the target, twenty-five N-(2-arylethyl) isoquinoline derivatives were designed, synthesized and evaluated for their antagonistic activities for CD36-oxidatively low density lipoprotein (oxLDL) binding. The primary analysis of structure-activity relationship (SAR) indicated a methoxyl at the 7-position and a hydroxyl at the 6- or 8-position could afford good activities. Among these analogs, compounds 7e and 7t showed the potential CD36 antagonistic activities with IC(50) values of 0.2 and 0.8 mu g/mL, respectively. Furthermore, both of them could effectively inhibit oxLDL uptake in insect Sf9 cells overexpressing human CD36, and thus have been selected for further investigation. We consider N-(2-arylethyl) isoquinoline analogs to be a family of novel CD36 antagonists. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.022
• 作为产物：
  描述：

  2-苯乙胺 、 3,4-二甲氧基苄醇 在 [RuH(tBu-PNP(-))(CO)] 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以92%的产率得到N-(3,4-dimethoxybenzylidene)-2-phenylethanamine
  参考文献：
  名称：

  释放H2由醇和胺直接合成亚胺

  摘要：

  一目了然：在温和的中性条件下，醇和胺可仅由分子氢和水释放（见方案； R =异丙基，叔丁基），可直接有效地由醇和胺合成芳基和脂族亚胺。这种一般的，对环境无害的反应是由脱芳香化的钌PNP钳形配合物（0.2摩尔％）催化的，可以在甲苯中于惰性气氛或空气中进行。

  DOI：

  10.1002/anie.200907018

文献信息

• Direct Synthesis of Imines from Alcohols and Amines with Liberation of H2
  作者：Boopathy Gnanaprakasam、Jing Zhang、David Milstein

  DOI：10.1002/anie.200907018

  日期：2010.2.15

  A clean sweep: Aryl and aliphatic imines can be synthesized directly and efficiently from alcohols and amines under mild, neutral conditions with the liberation of only molecular hydrogen and water (see scheme; R=isopropyl, tert‐butyl). This general, environmentally benign reaction is catalyzed by a de‐aromatized ruthenium PNP pincer complex (0.2 mol %), and can proceed in toluene under an inert atmosphere

  一目了然：在温和的中性条件下，醇和胺可仅由分子氢和水释放（见方案； R =异丙基，叔丁基），可直接有效地由醇和胺合成芳基和脂族亚胺。这种一般的，对环境无害的反应是由脱芳香化的钌PNP钳形配合物（0.2摩尔％）催化的，可以在甲苯中于惰性气氛或空气中进行。
• Antifibrillatory Agents. The Preparation of Some N-Benzyl-N-methylphenethylamines
  作者：A. R. Surrey、A. Mooradian、R. A. Cutler、C. M. Suter、J. S. Buck

  DOI：10.1021/ja01175a050

  日期：1949.7
• Synthesis, structure–activity relationship and in vitro biological evaluation of N-arylethyl isoquinoline derivatives as Coxsackievirus B3 inhibitors
  作者：Yan-Xiang Wang、Yu-Huan Li、Ying-Hong Li、Rong-Mei Gao、Hui-Qiang Wang、Yan-Xin Liu、Li-Mei Gao、Qiao-Ni Lu、Jian-Dong Jiang、Dan-Qing Song

  DOI：10.1016/j.bmcl.2011.08.002

  日期：2011.10

  Currently, there is no approved antiviral drug for the infection caused by enteroviruses. A series of novel N-arylethyl isoquinoline derivatives defined with substituents on the ring A and C were designed, synthesized and evaluated in vitro for their activities against Coxsackievirus B3 (CVB3). The primary structure-activity relationship revealed that substituents on the ring A were not beneficial for the activity. Among these analogs synthesized, compound 7f bearing a methylenedioxy at the R(4) and R(5) positions afforded an anti-CVB3 activity and a reasonable selectivity index (SI = 26.8); furthermore, 7f exhibited a moderate activity against enterovirus 71 (EV71) with SI value of 9.0. Thus it has been selected as an anti-enteroviral lead compound for further investigation. (C) 2011 Elsevier Ltd. All rights reserved.
• SOME SUBSTITUTED DI-(BETA-PHENYLETHYL)-AMINES AND BENZYL-BETA-PHENYLETHYLAMINES
  作者：Johannes S. Buck

  DOI：10.1021/ja01357a023

  日期：1931.6
• von Strandtmann,M. et al., Journal of Heterocyclic Chemistry, 1969, vol. 6, p. 429 - 431
  作者：von Strandtmann,M. et al.

  DOI：——

  日期：——