4-{2-[(3,4-dimethoxy-benzylidene)-amino]-ethyl}-phenol | 58199-73-8

• 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: 4-{2-[(3,4-dimethoxy-benzylidene)-amino]-ethyl}-phenol
• 英文别名: Phenol, 2-[[[2-(3,4-dimethoxyphenyl)ethyl]imino]methyl]-；2-[2-(3,4-dimethoxyphenyl)ethyliminomethyl]phenol
• CAS: 58199-73-8
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: ASARVGFHKPGWSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  435.6±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 溶解度：
  >42.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{2-[(3,4-dimethoxy-benzylidene)-amino]-ethyl}-phenol 在 三氟乙酸 作用下， 反应 2.0h， 以2.11 g的产率得到2-(6,7-二甲氧基-1,2,3,4-四氢异喹啉-1-基)苯酚
  参考文献：
  名称：

  Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs

  摘要：

  利用Pictet-Spengler反应制备了隐柱系列的三种生物碱以及20种单分子和3种双分子1-芳基四氢异喹啉衍生物。

  DOI：

  10.1007/s10600-013-0507-2
• 作为产物：
  描述：

  水杨醛 、 3,4-二甲氧基苯乙胺 以 苯 为溶剂， 生成 4-{2-[(3,4-dimethoxy-benzylidene)-amino]-ethyl}-phenol
  参考文献：
  名称：

  Synthesis of 1-aryltetrahydroisoquinoline alkaloids and their analogs

  摘要：

  利用Pictet-Spengler反应制备了隐柱系列的三种生物碱以及20种单分子和3种双分子1-芳基四氢异喹啉衍生物。

  DOI：

  10.1007/s10600-013-0507-2

文献信息

• Half‐sandwich Ru (II) complexes containing (N, O) Schiff base ligands: Catalysts for base‐free transfer hydrogenation of ketones
  作者：C.E. Satheesh、Pushpanathan N. Sathish Kumar、P. Raghavendra Kumara、Ramasamy Karvembu、Amar Hosamani、M. Nethaji

  DOI：10.1002/aoc.5111

  日期：2019.10

  Two new half‐sandwich Ru (II)(p‐cymene) complexes (1 and 2) containing dopamine‐based (N, O) Schiff base ligands (L1H and L2H) were synthesized and characterized by FT‐IR, UV–Visible and 1H & 13C NMR spectral techniques, and elemental analyses. The spectroscopic and analytical data revealed monobasic bidentate coordination of the ligands with Ru ion. The molecular structures of L1H, L2H and 2 were

  合成了两种新的含多巴胺基（N，O）Schiff碱配体（L 1 H和L 2 H）的Ru（II）（p- cymene）半三明治Ru（II）（p- cymene）配合物（1和2），并通过FT-IR表征UV-Visible和1 H＆13 C NMR光谱技术，以及元素分析。光谱和分析数据显示配体与Ru离子的一元二齿配位。L 1 H，L 2 H和2的分子结构通过单晶X射线衍射研究进一步证实。复合体1和2 在85°C无碱条件下，以2-丙醇为氢源，用作酮的转移氢化催化剂。仲醇的优异收率，克规模的合成以及较高的TON和TOF都使该催化体系变得有趣。
• Synthesis and choleretic activity of 2-benzyltetrahydroisoquinoline derivatives
  作者：A. N. Nabiev、V. I. Vinogradova

  DOI：10.1007/bf02464307

  日期：1997.9

  Some of the N-benzyltetrahydroisoquinoline derivatives synthesized in our previous works [ 1, 2] exhibit a pronounced choleretic activity. However, we failed to find any data on the effect of these compounds on the process of bile secretion and the antitoxic function of liver in the available literature. In this connection it was of interest to continue our investigations on the synthesis of N-ben

  在我们之前的工作中合成的一些 N-苄基四氢异喹啉衍生物 [1, 2] 表现出明显的利胆活性。然而，我们未能在现有文献中找到有关这些化合物对胆汁分泌过程和肝脏抗毒功能影响的任何数据。在这方面，我们有兴趣继续研究 N-苄基四氢异喹啉的合成并研究它们的利胆活性。新的衍生物 (IX) 是使用高戊烯胺或高胡椒胺和取代的苯甲醛 [3] 合成的，这些苯甲醛是通过相应的苯甲醛 [4, 5] 的卤化或氮化获得的。
• Synthesis, structural characterization, antimicrobial and DNA binding studies of homoleptic zinc and copper complexes of NO Schiff bases derived from homoveratrylamine
  作者：C.E. Satheesh、P. Raghavendra Kumar、N. Shivakumar、K. Lingaraju、P. Murali Krishna、H. Rajanaika、Amar Hosamani

  DOI：10.1016/j.ica.2019.05.028

  日期：2019.9

  Abstract Four new homoleptic zinc (1 and 2) and copper (3 and 4) complexes of two Schiff base ligands (L1H and L2H) derived from 2-(3,4-dimethoxyphenyl)ethan-1-amine (5), a dimethyl derivative of dopamine were synthesized. All four complexes were well characterized by elemental analysis, FT-IR and UV–Vis., spectroscopy. Further, the zinc complexes (1 and 2) were characterized by 1H and 13C1H} NMR

  摘要由2-二甲基（3-，4-二甲氧基苯基）乙烷-1-胺（5）衍生的两个席夫碱配体（L1H和L2H）的四个新的均配锌（1和2）和铜（3和4）配合物合成了多巴胺的衍生物。通过元素分析，FT-IR和UV-Vis。，光谱学对这四个复合物进行了很好的表征。此外，锌配合物（1和2）通过1H和13C 1H} NMR光谱表征，而铜配合物（3和4）通过单晶X射线衍射表征。配合物的表征数据显示，去质子化配体（L1和L2）作为组分[Zn / Cu（L1-2）2]的NO供体，通过甲亚胺氮（N）和苯酚氧（O）具有很强的配位作用（1-4）。复合物的CT-DNA结合亲和力1，使用电子吸收滴定法评估图2和图4，该图显示了通过嵌入模式的狂热结合，发现结合常数（Kb）约为105–106 M-1。通过琼脂井扩散方法针对致病性抗菌菌株大肠杆菌，金黄色葡萄球菌和抗真菌菌株白色念珠菌筛选化合物（1-5）的剂量依赖性抗菌活性。该化合物对这些病原体显示出显着的毒性。
• Synthesis, characterisation and antimicrobial activity of new palladium and nickel complexes containing Schiff bases
  作者：C.E. Satheesh、P. Raghavendra Kumar、P. Sharma、K. Lingaraju、B.S. Palakshamurthy、H. Raja Naika

  DOI：10.1016/j.ica.2015.11.017

  日期：2016.3

  New Schiff base ligands were synthesized by condensation of 2-(3,4-dimethoxyphenyl)ethanamine with 2-hydroxy benzaldehyde ((LH)-H-1) and 2'-hydroxy acetophenone ((LH)-H-2) respectively. Reaction of (LH)-H-1 or (LH)-H-2 with Na2PdCl4 or NiCl2 center dot 6H(2)O in 2:1 ratio obtained four new coordination complexes [M(L1-2)(2)] (where M = Pd(II); 1 and 2 and M = Ni(II); 3 and 4). Both the ligands and four complexes were characterised by elemental analysis, FT-IR and UV-Vis, spectroscopy. (LH)-H-1, (LH)-H-2, 1 and 2 were also characterised by H-1 and C-13H-1} NMR spectroscopy. The molecular structures of 1 and 3 were determined by single crystal X-ray diffraction. The spectroscopic and crystal structure data showed that the ligands coordinated to M (II) ion in a bidentate monoanionic (O , N) fashion. The Pd-O and Pd-N bond lengths in 1 are 1.984(11) and 2.020(12) angstrom in 3 the Ni-O and Ni-N bond lengths are 1.8222(13) and 1.9262(15) angstrom respectively. The C=N bond length in 3 found 1.290(2) angstrom which was shorter than 1.310(19) angstrom in 1. The bond angles provided square planar geometry around Pd(II) and Ni(II) in both 1 and 3. There exists C-H center dot center dot center dot O type (2.50-2.52 angstrom) intermolecular hydrogen bonding in both 1 and 3 resulting in supramolecular structures. The antimicrobial activity of new Schiff base ligands and their Pd(II) and Ni(II) complexes against pathogenic microbial strains by agar well diffusion method was conducted. All the ligands and complexes showed significant antibacterial and antifungal activities. The bacterial and fungi growth inhibition activity of ligands has been increased on complexation as well as among complexes palladium complexes were found better antibacterial and antifungal agents than the nickel complexes of corresponding ligands. Ligand (LH)-H-1 and the complex 2 showed highest antibacterial activity against Pseudomonas desmolyticum and highest antifungal activity against Candida albicans. (C) 2015 Elsevier B.V. All rights reserved.