4-chloro-2-[(2-morpholin-4-yl-ethylimino)-methyl]-phenol | 27528-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-chloro-2-[(2-morpholin-4-yl-ethylimino)-methyl]-phenol
• 英文别名: 4-Chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol；4-chloro-2-(2-morpholin-4-ylethyliminomethyl)phenol
• CAS: 27528-46-7
• 化学式: C₁₃H₁₇ClN₂O₂
• 分子量: 268.743
• InChiKey: JJPIOHMPYLDJSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  45.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-2-[(2-morpholin-4-yl-ethylimino)-methyl]-phenol 、 copper(II) nitrate trihydrate 以 甲醇 为溶剂， 生成 Cu(4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenolate)2
  参考文献：
  名称：

  Synthesis, structural characterization and in vitro cytotoxicity assessment of new mononuclear Cu(II) and Co(II) complexes against MDA–MB–231, HCC–1806 and HT–29 cancer cell lines

  摘要：

  DOI：

  10.1016/j.poly.2022.116189
• 作为产物：
  描述：

  N-(2-氨基乙基)吗啉 、 5-氯代水杨醛 以 甲醇 为溶剂， 反应 0.5h， 以95%的产率得到4-chloro-2-[(2-morpholin-4-yl-ethylimino)-methyl]-phenol
  参考文献：
  名称：

  两种具有抗菌活性的席夫碱铜(II)配合物的合成及晶体结构

  摘要：

  两种结构相似的三核配合物，[Cu(Cu(μ-Cl)2L1)2] (1) 和 [Cu(Cu(μ-Cl)2L2)2] (2) (HL1 = 4-chloro-2-[( 2-morpholin-4-ylethylimino)methyl]phenol, HL2 = 1-[(2-piperin-1ylethylimino)methyl]naphthalen-2-ol)，已经合成并进行了结构表征。两种配合物都是桥连的三核化合物。每个复合物中的中心铜处于八面体环境中，具有两个酚盐和四个桥接氯化物。每个配合物中与对称性相关的末端 Cu 是方锥体，具有一个酚盐氧、一个亚胺氮和一个席夫碱配体的胺氮，基面有一个 Cl-，顶端位置有一个桥连 Cl-。复合物和席夫碱在体外测试了它们的抗菌活性。

  DOI：

  10.1080/00958970903401863

文献信息

• A series of mononuclear nickel(II) complexes of Schiff-base ligands having N,N,O- and N,N,N-donor sites: Syntheses, crystal structures, solid state thermal property and catecholase-like activity
  作者：Averi Guha、Kazi Sabnam Banu、Sudhanshu Das、Tanmay Chattopadhyay、Ria Sanyal、Ennio Zangrando、Debasis Das

  DOI：10.1016/j.poly.2012.07.088

  日期：2013.3

  [NiL4(ClBz)(H2O)]·1.25(H2O) (4) have been synthesized via Schiff-base formation by condensation between 2-benzoylpyridine and N-(2-aminoethyl)pyrrolidine for L1, salicylaldehyde and N-(2-aminoethyl)piperazine (L2), 5-chlorosalicylaldehyde and N-(2-aminoethyl)piperazine (L3), and 5-chlorosalicylaldehyde and N-(2-aminoethyl)morpholine (L4). These complexes are comprehensively characterized via routine physicochemical

  摘要四种新的单核镍（II）配合物，即[NiL1（H2O）3]（NO3）2（1），[NiL2（ ）3]（ ）2（2），[NiL3（ ）3]（ ）2（3）和[NiL4（ClBz）（ ）]·1.25（ ）（4）通过席夫碱形成，通过2-苯甲酰基吡啶和N-（2-氨基乙基）吡咯烷之间的缩合反应合成L1，水杨醛N-（2-氨基乙基）哌嗪（L2），5-氯水杨醛和N-（2-氨基乙基）哌嗪（L3），5-氯水杨醛和N-（2-氨基乙基）吗啉（L4）。这些配合物通过常规物理化学技术以及单晶X射线结构分析得到全面表征。尽管所有的镍络合物都是单核的，但儿茶酚酶的活性却显示出明显的变化，这取决于金属中心周围的配位环境。衍生自相同胺的配合物2和3在配体系统上带有额外的正电荷，有助于底物与催化剂的相互作用，从而促进3,5-DTBC氧化为3,5-DTBQ。相反，尽管配合物1和4在活性上与镍取代的邻苯二酚
• Synthesis and crystal structures of two Schiff base copper(II) complexes derived from 4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol
  作者：Y. L. Sang、X. S. Lin

  DOI：10.1134/s1070328410060096

  日期：2010.6

  A centrosymmetric mononuclear copper(II) complex, [Cu(L1)2] (I), and a phenolate oxygen-bridged dinuclear copper(II) complex, [Cu2(L2)4] (II) (HL1 = 4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol, HL2 = 4-chloro-2-(cyclohexylimino-methyl)phenol), were synthesized and characterized by elemental analyses, IR, and single crystal X-ray diffraction. The crystal of I is monoclinic: space group ITP}21/n

  中心对称单核铜（II）配合物[Cu（L 1）2 ]（I）和酚盐氧桥双核铜（II）配合物[Cu 2（L 2）4 ]（II）（HL 1 =合成了4-氯-2-[（2-吗啉-4-基乙基亚氨基）甲基]苯酚，HL 2 = 4-氯-2-（环己基氨基甲基）苯酚，并通过元素分析，红外光谱和单晶表征X射线衍射。I的晶体是单斜晶的：空间群ITP} 2 1 / n，a = 13.396（3），b = 5.339（1），c = 19.740（4）Å，β= 108.64（3），V = 1337.8（ 5）3，ITZ} = 2。II的晶体是单斜晶的：空间群P 2 1，a = 9.157（2），b = 22.715（4），c = 12.169（2）Å，= 95.28（3），ITV } = 2520.4（8）Å3，ITZ} =2。位于反转中心的I中的Cu原子在正方形平面几何结构中为四坐标，带有两个酚盐氧和两个亚胺氮
• Synthesis and crystal structures of cobalt(III) and zinc(II) complexes derived from 4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol with urease inhibitory activity
  作者：C. Y. Wang

  DOI：10.1134/s1070328410030036

  日期：2010.3

  A new mononuclear cobalt(III) complex, [CoL2(N3)]2 · CH3OH (I), and a new mononuclear zinc(II) complex, [ZnLCl(CH3OH)] (II) (HL = 4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol), were prepared and structurally characterized by elemental analyses, infrared spectroscopy, and single- crystal X-ray diffraction. The crystal of I is monoclinic: space group P21/c, a = 18.742(2) Å, b = 15.197(2) Å,

  一种新的单核钴（III）配合物[CoL 2（N 3）] 2 ·CH 3 OH（I）和一种新的单核锌（II）配合物[ZnLCl（CH 3 OH）]（II）（HL =制备了4-氯-2-[（（2-吗啉-4-基乙基亚氨基）甲基]苯酚]，并通过元素分析，红外光谱和单晶X射线衍射对其结构进行了表征。I的晶体是单斜晶的：空间群P 2 1 / c，a = 18.742（2）Å，b = 15.197（2）Å，c = 25.646（2）Å，β= 125.996（3）°，V = 5909.8 （11）Å3，Z = 4。II的晶体是单斜晶的：空间群P 2 1 / c，a = 7.257（1）Å，b = 24.707（2）Å，c = 9.637（1）Å，β= 101.557（2） ）°，V = 1692.9（3）3，ž = 4。Co的原子我是在八面体配位，并且在锌原子II处于三角-双锥协调。脲酶抑制试验表明，复合物
• Synthesis, Characterization, and Crystal Structures of Two Dioxovanadium(V) Complexes with Schiff Bases
  作者：Shi-Yong Liu、Ren-Hua Zheng、Yu-Ping Ma、Zhonglu You

  DOI：10.1080/15533174.2010.522670

  日期：2011.1.31

  dioxovanadium(V) complexes, [VO2L1]2 (1) and [VO2L2] (2), where L1 and L2 are the deprotonated forms of 4-chloro-2-[(2-isopropylaminoethylimino)methyl]phenol and 4-chloro-2-[(2-morpholin-4-ylethylimino)methyl]phenol, respectively, have been synthesized and characterized by IR spectra and single crystal X-ray diffraction. Complex (1) is a centrosymmetric dinuclear dioxovanadium complex, with the V atom six-coordinate

  两个新的二氧钒钒（V）络合物，[VO 2 L1] 2（1）和[VO 2 L2]（2），其中L1和L2是4-氯-2-[（2-异丙基氨基乙基亚氨基）甲基]的去质子化形式分别合成了苯酚和4-氯-2-[（2-吗啉-4-基乙基亚氨基）甲基]苯酚，并通过红外光谱和单晶X射线衍射对其进行了表征。配合物（1）是一个中心对称的双核二氧钒钒配合物，V原子的六坐标为八面体几何形状。V⋅⋅⋅V距离为3.224（2）Å。配合物（2）是单核二氧钒配合物，V原子五坐标呈扭曲的方形锥体形状。Schiff碱配体中端基的空间效应会影响配合物的结构。
• Combined Experimental and Theoretical Investigation of Ligand and Anion Controlled Complex Formation with Unprecedented Structural Features and Photoluminescence Properties of Zinc(II) Complexes
  作者：Prateeti Chakraborty、Jaydeep Adhikary、Sugata Samanta、Daniel Escudero、Abril C. Castro、Marcel Swart、Sanjib Ghosh、Antonio Bauzá、Antonio Frontera、Ennio Zangrando、Debasis Das

  DOI：10.1021/cg500717n

  日期：2014.8.6

  By using two potential tridentate ligands, HL1 [4-chloro-2-[(2-morpholin-4-yl-ethylimino)-methyl]-phenol] and 4-chloro-2-[(3-morpholin-4-yl-propylimino)-methyl]-phenol], which differ by one methylene group in the alkyl chain, four new Zn-II complexes, namely, [Zn((LH)-H-2)(2)](ClO4)(2) (1), [Zn(L-1))(H2O)(2)][Zn(L-1)(SCN)(2)] (2), [Zn(L-1))(dca)](n) (3), and [Zn-2(L-1)(2)(N-3)(2)(H2O)(2)] (4) [where dca = dicyanamide anion] were synthesized and structurally characterized. The results indicate that the slight structural difference between the ligands, HL1 and HL2, because of the one methylene group connecting the nitrogen atoms provokes a chemical behavior completely different from what was expected. Any attempt to isolate the Zn(L-2) complexes with thiocyanato, dicyanamido, and azide was unsuccessful, and perchlorate complex 1 was always obtained. In contrast, with HL1) we obtained structural diversity on varying the anions, but we failed to isolate the analogous perchlorate complex of HI). Single-crystal X-ray analyses revealed that the morpholine nitrogen of ligand L2 is protonated and thus does not take part in coordination with Zn-II in complex 1. On the other hand, the morpholine nitrogen of L-1 is coordinated to Zn-II in 2-4. Of these, 2 and 4 are rare examples of a cocrystallized cationic/anionic complex and of a dinuclear complex bridged by a single azide, respectively. Some of these unexpected findings and some interesting noncovalent interactions leading to the formation of dimeric entities in solid-state compound 4 were rationalized by a DFT approach. Photoluminescence properties of the complexes as well as the ligands were investigated in solution at ambient temperature and at 77 K. The very fast photoinduced electron transfer (PET) from the nitrogen lone pair to the conjugated phenolic moiety is responsible for very low quantum yield (Phi) exhibited by the ligands, whereas complexation prevents PET, thus enhancing the Phi in the complexes. The origin of the electronic and photoluminescence properties of the ligands and complexes was assessed in light of theoretical calculations.