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

• Manganese-Catalyzed Environmentally Benign Dehydrogenative Coupling of Alcohols and Amines to Form Aldimines and H₂: A Catalytic and Mechanistic Study
  作者：Arup Mukherjee、Alexander Nerush、Gregory Leitus、Linda J. W. Shimon、Yehoshoa Ben David、Noel Angel Espinosa Jalapa、David Milstein

  DOI：10.1021/jacs.5b13519

  日期：2016.4.6

  The catalytic dehydrogenative coupling of alcohols and amines to form aldimines represents an environmentally benign methodology in organic chemistry. This has been accomplished in recent years mainly with precious-metal-based catalysts. We present the dehydrogenative coupling of alcohols and amines to form imines and H2 that is catalyzed, for the first time, by a complex of the earth-abundant Mn.

  醇和胺的催化脱氢偶联形成醛亚胺代表了有机化学中一种环境友好的方法。近年来，这主要是通过贵金属基催化剂实现的。我们提出了醇和胺脱氢偶联形成亚胺和 H2 的过程，这是第一次由地球上丰富的 Mn 络合物催化。借助核磁共振光谱、中间分离和 X 射线分析进行了详细的机械研究。
• 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：——