2-[2-bromoethyliminomethyl]phenol | 80622-20-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[2-bromoethyliminomethyl]phenol
• 英文别名: N-salicyldene-2-bromoethylamine；2-(2-Bromoethyliminomethyl)phenol
• CAS: 80622-20-4
• 化学式: C₉H₁₀BrNO
• 分子量: 228.088
• InChiKey: HBQKSOSNRPNAEI-UHFFFAOYSA-N

物化性质

• 沸点：
  305.3±27.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[2-bromoethyliminomethyl]phenol 在 六氟磷酸钾 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  空气稳定的席夫碱官能化 N-杂环卡宾配体的 Ni(II) 配合物作为脂肪族酮转移加氢催化剂的应用

  摘要：

  摘要 2-[-2-[3-(R)imidazol-1-yl]ethyliminomethyl]phenol [R =methyl (2), 2-pyridylmethyl]phenol [R = 甲基 (2), 2-吡啶甲基(3)] 合成并通过 NMR、IR、MS 和 CHN 分析表征。对其 Ni(II) 配合物的单晶 X 射线结构分析显示，螯合配体以三齿 (2, C^N^O) 和四齿 (3, N^C^N^O) 模式配位的方形平面排列在金属。这三个新的分离和完全表征的配合物被用作催化剂，用于脂肪族酮在 2-丙醇中作为溶剂和氢源的催化转移氢化。基于 0.2 mol% 的催化剂浓度，复合物对脂肪族酮表现出活性，对环己酮和所有测试的芳香酮表现出 100% 的转化率（500 的转化率）。图形概要

  DOI：

  10.1080/00958972.2018.1493199

文献信息

• Transfer hydrogenation of ketones catalyzed by a trinuclear Ni(II) complex of a Schiff base functionalized N-heterocyclic carbene ligand
  作者：Samaila Abubakar、Halliru Ibrahim、Muhammad D. Bala

  DOI：10.1016/j.ica.2018.09.057

  日期：2019.1

  (O1) and imine nitrogen donor (N1) atoms in a trans [N^O^(Ni2+)^N^O] mode, whilst the carbene moieties of each bridging ligand and a tridentate L are coordinated in a distorted square planar CNHC-(Ni2+)^N^O^CNHC mode to stabilise each of the terminal Ni(II) ions. Complex 4 showed significant activity as a catalyst in the transfer hydrogenation of a range of aliphatic and aromatic ketones, at a catalyst

  同时每个桥联配体的碳烯部分和三齿L以扭曲的方形平面CNHC-（Ni2 +）^ N ^ O ^ CNHC模式进行配位，以稳定每个末端Ni（II）离子。配合物4在0.1mol％的催化剂浓度下，在一系列脂族和芳族酮的转移氢化中显示出显着的催化剂活性。4小时后，芳族酮的转化率高达100％。
• Zinc, copper and nickel derivatives of 2-[2-bromoethyliminomethyl]phenol as topoisomerase inhibitors exhibiting anti-proliferative and anti-metastatic properties
  作者：Sze Koon Lee、Kong Wai Tan、Seik Weng Ng

  DOI：10.1039/c4ra09256b

  日期：——

  (M is zinc, copper and nickel) along with Ni[OC6H4CHNCH2CH2]2(H2O)4·2Br, were found to inhibit topoisomerase I (topo I) activity, induce DNA cleavage and bind to calf thymus DNA. The compounds were found to be cytotoxic when tested against cancer cell lines (A2780, MCF-7, HT29, HepG2, A549, PC3, LNCaP), and were anti-invasive against PC3. The inhibitory strength of the metal complexes was higher than

  （2- [2-溴乙基亚氨基甲基]苯酚），M [OC 6 H 4 CH NCH 2 CH 2 Br] 2（M为锌，铜和镍）的三种过渡金属衍生物以及Ni [OC 6 H 4 CH NCH 2 CH 2 ] 2（H 2 O）4·2Br被发现抑制拓扑异构酶I（拓扑I）的活性，诱导DNA裂解并与小牛胸腺DNA结合。当测试这些化合物对癌细胞系（A2780，MCF-7，HT29，HepG2，A549，PC3，LNCaP）具有细胞毒性，并且对PC3具有抗侵害性。金属配合物的抑制强度高于有机化合物的抑制强度。中性金属配合物是通过金属乙酸盐与席夫碱配体的反应合成的，而溴化物盐是在镍衍生物从水中重结晶后获得的。在该盐的晶体结构中，环化的席夫碱配体通过其氮供体与镍原子结合，金属原子显示出全反八面体的几何形状。Cu [OC 6 H4 CHNCH 2 CH 2 Br] 2存在于正方形平面的环境中。
• Synthesis, characterization and crystal structures of new bidentate Schiff base ligand and its vanadium(IV) complex: The catalytic activity of vanadyl complex in epoxidation of alkenes
  作者：Gholamhossein Grivani、Aliakbar Dehno Khalaji、Vida Tahmasebi、Kazuma Gotoh、Hiroyuki Ishida

  DOI：10.1016/j.poly.2011.09.011

  日期：2012.1

  The Schiff base ligand N-salicylidin-2-bromoethylimine (L) and its vanadium(IV) complex, VOL2 (1), were synthesized and characterized by using X-ray, CHN, H-1 NMR and FT-IR methods. X-ray analysis shows the Schiff base ligand L acts as a bidentate (O, N) chelating ligand and coordinates via imine nitrogen and phenolato oxygen atoms to the V(IV) center. The coordination geometry around the V(IV) center in 1 is approximately square pyramidal, as indicated by the unequal metal-ligand bond distances and angles, with the basal plane formed by the N2O2 donors of the two bidentate Schiff base ligands, the two phenolato O atoms and the two imine N atoms are in the trans position. The coordination sphere of the V(IV) is completed by one oxygen atom in apical position. In the Schiff base ligand, L, there are some classical intramolecular O1-H1 center dot center dot center dot N1 and non-classical intermolecular C9-H9b center dot center dot center dot O1 hydrogen bonds, while in 1, there are two non-classical intermolecular C7-H7 center dot center dot center dot O3 and C8-H8b center dot center dot center dot O3 hydrogen bonds. The catalytic activity of 1 in epoxidation of cyclooctene was investigated in different conditions to obtain optimum conditions. The effects of solvent, oxidant, catalyst concentration and alkene/oxidant ratio were studied and the results showed that in CCl4 in the presence of tert-butylhydroperoxide in 1:3 alkene/oxidant ratio, high epoxide yield was obtained. The epoxidation of alkenes was also carried out in optimized conditions that high catalytic activity and selectivity were obtained. (C) 2011 Elsevier Ltd. All rights reserved.