2-methoxy-6-(pyridin-2-yl-hydrazonomethyl) phenol | 111781-93-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-methoxy-6-(pyridin-2-yl-hydrazonomethyl) phenol
• 英文别名: 2-methoxy-6-(pyridin-2-yl-hydrazonomethyl)-phenol；2-methoxy-6-(pyridine-2-ylhydrazonomethyl)phenol；2-methoxy-6-(pyridin-2-ylhydrazonomethyl)phenol；2-Methoxy-6-[(pyridin-2-ylhydrazinylidene)methyl]phenol
• CAS: 111781-93-2
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: FFZWBZJRENXDNU-UHFFFAOYSA-N

物化性质

• 沸点：
  425.4±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  66.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonate)oxovanadium 、 2-methoxy-6-(pyridin-2-yl-hydrazonomethyl) phenol 以 甲醇 为溶剂， 反应 20.0h， 以84%的产率得到
  参考文献：
  名称：

  New metal complexes of NNO tridentate ligands: Effect of metal center and co-ligand on biological activity

  摘要：

  In the search for new agents against Ttypanosoma cruzi and cancer the effect of the nature of the metal center and of the presence of a polypiridyl coligand on the antitrypanosomal and antitumoral activities of selected N,N,O ligands [2-(benzothiazol-2-yl hydrazonomethyl phenol (HL1) and 2-(benzothiazol-2-yl-hydrazonomethyl)-6-methoxyphenol (HL2)] is explored. The new complexes [(VO2)-O-V(L1)I, [(VO2)-O-V(L2)], [(VO)-O-IV(L1-H)(phen))] and [Ga-III(L2)(2)](NO3) were synthesized and characterized by using different techniques. The stability of the vanadium complexes in solution was investigated by EPR and V-51 NMR spectroscopies and that of the gallium compound by UV-Vis spectroscopy, H-1 NMR and conductivity measurements. While the vanadium complexes show high stability in DMSO, the gallium complex shows very good stability in DMSO and moderate stability in aqueous - DMSO medium.The cytotoxicity on human tumor cell lines (ovarian A2780, breast MCF7 and prostate PC3 cell lines) that show different sensitivity to cisplatin was evaluated. All the compounds evidenced antiproliferative activity in the micromolar range. The highest cytotoxic activity, in molar units, is shown by [Ga-III(L2)(2)](-NO3) (IC50: 1.7 mu M) and [(VO)-O-IV(L1-H)(phen)] (IC50: 2.7 mu M) against the ovarian cancer cells. With the exception of [(VO2)-O-V(L1)], the cytotoxic activity of the ligands and complexes is similar to that of cisplatin in A2780 cells and surpass cisplatin in the other tumor cells. Regarding the activity on T. cruzi, [(VO)-O-IV(L1-H)(phen)] showed a 10-fold decrease of IC50 with respect to HL1 and an IC50 value (10.7 mu M) in the same order of that of the antitrypanosomal drug Nifurtimox (IC50: 6.0 mu M). HL2 showed significant growth inhibitory effect on the parasite (IC50: 23.5 mu M) and its coordination to Ga(III) lead to a 2-fold increase in activity in molar units (IC50: 14.2 mu M). In order to explain the high inhibitory activity of [(VO)-O-IV(L1-H)(phen)] against the parasite and the tumor cells, the interaction of this compound with plasmid DNA was preliminarily evaluated by AFM. The corresponding images suggest that DNA may be considered as a potential target. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.10.022
• 作为产物：
  描述：

  2-肼吡啶 、 邻香草醛 以 乙醇 为溶剂， 反应 2.0h， 以93.63%的产率得到2-methoxy-6-(pyridin-2-yl-hydrazonomethyl) phenol
  参考文献：
  名称：

  含有N，N，O-三齿配体的钯配合物催化的便捷高效的Suzuki-Miyaura交叉偶联反应

  摘要：

  Ñ，Ñ，ö -Tridentate配体1 - 9从胺与9种芳族醛或酮的缩合制备的。这些配体是热稳定的，对空气和湿气都不敏感。2-甲氧基-6-[（吡啶-2-基甲基亚氨基）-甲基]-苯酚1或2-（苯并噻唑-2-基-肼基甲基）-4,6-二叔丁基-苯酚6的组合与Pd（OAc）2为各种芳基溴化物与芳基硼酸的Suzuki-Miyaura交叉偶联提供了极好的催化剂前体。研究了不同溶剂，碱和配体/钯比例对偶联反应性能的影响。游离配体1及其乙酸钯络合物10的分子结构均通过单晶X射线衍射法测定。DFT研究表明，涉及这类配体的钯配合物的催化性能可能会因其结构的微小变化而大不相同。

  DOI：

  10.1016/j.tet.2009.02.017

文献信息

• Two-Step Spin-Transition Iron(III) Compound with a Wide [High Spin-Low Spin] Plateau
  作者：Jinkui Tang、José Sánchez Costa、Simon Smulders、Gábor Molnár、Azzedine Bousseksou、Simon J. Teat、Yangguang Li、Gerard A. van Albada、Patrick Gamez、Jan Reedijk

  DOI：10.1021/ic801973x

  日期：2009.3.2

  reveals the presence of two slightly different iron(III) centers in pseudo-octahedral environments generated by two deprotonated tridentate mph ligands. The presence of hydrogen bonding interactions, instigated by the well-designed ligand, may justify the occurrence of the abrupt transitions. 1 has been characterized by temperature-dependent magnetic susceptibility measurements, EPR spectroscopy, differential

  从具有N，N，O供体组的肼基希夫碱配体合成了一种新的铁（III）配位化合物，该化合物具有两步自旋转变行为，具有约45 K的[HS-LS]平稳期即2-甲氧基-6-（吡啶-2- ylhydrazonomethyl）苯酚（哼）。在150 K下测定的配位化合物[Fe（mph）2 ]（ClO 4）（MeOH）0.5（H 2 O）0.5 } 2（1）的单晶X射线结构显示存在两个略有不同的两个去质子化的三齿时速产生的伪八面体环境中的铁（III）中心配体。通过精心设计的配体引起的氢键相互作用的存在可以证明突变的发生是合理的。图1的特征是依赖于温度的磁化率测量，EPR光谱，差示扫描量热法和57 FeMössbauer光谱，这些都证实了两步转变的发生。另外，高自旋态的铁（III）物种已被捕获并通过快速冷却EPR研究进行了表征。
• Synthesis, structure, and magnetism of non-planar heptanuclear lanthanide(<scp>iii</scp>) complexes
  作者：Joydeb Goura、James P. S. Walsh、Floriana Tuna、Vadapalli Chandrasekhar

  DOI：10.1039/c4dt01603c

  日期：——

  The reaction of the hydrazone, 2-methoxy-6-(pyridin-2-yl-hydrazonomethyl) phenol (LH) with lanthanide(III) nitrate salts in the presence of excess triethylamine afforded the heptanuclear Ln(III) complexes: [Gd7(L)6(μ3-OH)8(NO3)4(H2O)]·(NO3)3·8CH3CN·H2O (1), [Tb7(L)6(μ3-OH)8(NO3)4]·(NO3)3·9CH3CN·2CH3OH·3H2O (2), [Dy7(L)6(μ3-OH)8(NO3)4(H2O)]·(NO3)3·7CH3CN·3H2O (3), [Ho7(L)6(μ3-OH)8(NO3)4]·(NO3)3·11CH3CN·2CH3OH·2H2O

  在过量的三乙胺存在下，,、2-甲氧基-6-（吡啶-2-基-肼基甲基）苯酚（LH）与硝酸镧（III）盐的反应提供了七核的Ln（III）配合物：[Gd 7（L）6（μ 3 -OH）8（NO 3）4（H 2 O）]·（NO 3）3 ·8CH 3 CN·H 2 O（1），[TB 7（L）6（μ 3 -OH）8（NO 3）4 ]·（NO 3）3·9CH 3 CN·2CH 3 OH·3H 2 O（2），[镝7（L）6（μ 3 -OH）8（NO 3）4（H 2 O）]·（NO 3）3 ·7CH 3 CN·3H 2 O（3），[HO 7（L）6（μ 3 -OH）8（NO 3）4 ]·（NO 3）3 ·11CH 3 CN·2CH 3 OH·2H 2 O（4）和[二7（L）6（μ 3 -OH）8（NO 3）4 ]·（NO 3）3 ·8CH 3 CN·2CH 3 OH（5）。单晶X射线衍射研究表明，这些配合物是
• On the nature of the high-spin (6A1) ⇌ low-spin (2T2) transition in [Fe(3-CH3OSPH)2]Y complexes
  作者：Madan Mohan、Niranjan S. Gupta、Lakhami Chandra、Narendra K. Jha、Radhey S. Prasad

  DOI：10.1016/s0020-1693(00)83908-0

  日期：1988.1
• Tetranuclear Lanthanide(III) Complexes in a Seesaw Geometry: Synthesis, Structure, and Magnetism
  作者：Joydeb Goura、James P. S. Walsh、Floriana Tuna、Vadapalli Chandrasekhar

  DOI：10.1021/ic4027915

  日期：2014.4.7

  The reaction of 2-methoxy-6-(pyridin-2-ylhydrazonomethyl)phenol (LH) with Ln(III) (Ln = Gd, Tb, Dy, Ho) salts in the presence of an excess of triethylamine afforded [Gd-4(L)(4)(mu(4)-OH)(mu(3)-OH)(2)(NO3)(4)]center dot(NO3)center dot 4CH(3)CN center dot CH3OH center dot 2H(2)O (1), [Tb-4(L)(4)(mu(4)-OH)(mu 3-OH)(2)(NO3)(4)]center dot(NO3).4CH(3)CN center dot 3H(2)O (2), [Dy-4(L)(4)(mu(4)-OH)(mu(3)-OH)(2)(NO3)(4)]center dot(NO3) 6CH(3)CN center dot H2O (3), and [Ho-4(L)(4)(mu(4)-OH)(mu-OH)(2)(NO3)(4)]center dot(NO3)center dot 8CH(3)CN center dot 3CH(3)OH center dot 2H(2)O (4). All four complexes contain a monocationic tetranuclear core with a unique seesaw topology. The tetranuclear assembly is formed through the coordination of four [L], one mu(4)-OH, two mu(3)-OH, and four chelating nitrate ligands, with a charge-balancing nitrate counteranion. Magnetic studies reveal a weak antiferromagnetic coupling throughout the series. Compound 1 can be modeled well with an isotropic exchange between all centers parametrized by J = -0.09 cm(-1). Compound 3 exhibits slow magnetic relaxation at low temperatures.
• Supramolecular Click Assembly of a Fused Double‐Stranded [Mn ^II ₃ ] Dihelicate
  作者：Jinkui Tang、José Sánchez Costa、Guillem Aromí、Ilpo Mutikainen、Urho Turpeinen、Patrick Gamez、Jan Reedijk

  DOI：10.1002/ejic.200700697

  日期：2007.9

  AbstractA trinuclear MnII complex was obtained by reaction of manganese(II) perchlorate with the ligand 2‐methoxy‐6‐(pyridine‐2‐ylhydrazonomethyl)phenol in methanol. The X‐ray crystal structure of [Mn3L4](ClO4)2(H2O)2 (1) reveals that the “bent” chain of the MnII ions is assembled by a unique click‐assembly of two double‐stranded helicates. Magnetic susceptibility measurements show weak ferromagnetic interactions between the metal ions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)