4-chloro-2-[(3-morpholin-4-yl-propylimino)-methyl]-phenol | 1393088-23-7

• 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-[(3-morpholin-4-yl-propylimino)-methyl]-phenol
• 英文别名: 4-Chloro-2-(3-morpholin-4-ylpropyliminomethyl)phenol
• CAS: 1393088-23-7
• 化学式: C₁₄H₁₉ClN₂O₂
• 分子量: 282.77
• InChiKey: RQRQOOGDMBUMMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-[(3-morpholin-4-yl-propylimino)-methyl]-phenol 、 zinc dibromide 以 甲醇 为溶剂， 反应 0.5h， 以36%的产率得到[ZnBr(4-chloro-2-[(3-(morpholin-4-yl)propylimino)methyl]phenolate)]
  参考文献：
  名称：

  Syntheses, crystal structures, and fluorescence properties of Zinc(II) complexes with multi-dentate Schiff bases

  摘要：

  Two new structurally similar mononuclear Schiff base zinc(II) complexes, [ZnBr(ClMP)] (I) and [ZnCl(NMP)] (II) (ClMP = 4-chloro-2-[(3-morpholin-4-ylpropylimino)methyl]phenolate; NMP = 4-nitro-2-[(3-morpholin-4-ylpropylimino)methyl]phenolate), and two new dinuclear Schiff base zinc(II) complexes, [Zn-2(EMP)(2)I-2] (III), and [Zn-2(MPA)(CH3OH)(2)(N-3)(2)] (IV) (EMP = 5-diethylamino-2-[(2-dimethylaminoethylimino)methyl]phenolate; MPA = N,N'-bis(3-methoxysalicylidene)propane-1,3-diamine), have been prepared and characterized mainly by single-cyrstal X-ray diffraction. Complex I crystallizes in the monoclinic space group P2(1)/n with unit cell dimensions: a = 15.116(3), b = 9.465(1), c = 23.714(4) , beta = 104.358(2)A degrees, V = 3286.9(8) (3), Z = 8, R (1) = 0.0439, and wR (2) = 0.0736. Complex II crystallizes in the monoclinic space group P2(1)/c with unit cell dimensions: a = 7.253(2), b = 16.652(4), c = 13.568(3) , beta = 96.600(2)A degrees, V = 1627.8(6) (3), Z = 4, R (1) = 0.0417, and wR (2) = 0.0809. Complex III crystallizes in the monoclinic space group C2/c with unit cell dimensions: a = 27.962(2), b = 8.246(2), c = 31.605(3) , beta = 90.343(2)A degrees, V = 7287.4(15) (3), Z = 8, R (1) = 0.0721, and wR (2) = 0.1709. Complex IV crystallizes in the monoclinic space group C2/c with unit cell dimensions: a = 20.483(3), b = 11.344(2), c = 14.909(3) , beta = 131.650(1)A degrees, V = 2588.6(7) (3), Z = 4, R (1) = 0.0343, and wR (2) = 0.0792. Each Zn atom in I and II are four-coordinated in a tetrahedral geometry by the NNO donor set of the Schiff base ligand and one halide atom. The Zn atoms in III are in square pyramidal coordination, and those in IV are in octahedral and tetrahedral coordination. Thermal stability and fluorescence properties of the complexes I and II have also been determined.

  DOI：

  10.1134/s1070328413110080
• 作为产物：
  描述：

  N-(3-氨丙基)吗啉 、 5-氯代水杨醛 以 乙醇 为溶剂， 反应 2.0h， 生成 4-chloro-2-[(3-morpholin-4-yl-propylimino)-methyl]-phenol
  参考文献：
  名称：

  N-(3-氨基丙基)吗啉衍生的两种柔性齿水杨醛亚胺配体对锌和铜的配位模式

  摘要：

  原位制备了由水杨醛或 5-氯水杨醛与 N-(3-氨基丙基) 吗啉缩合而成的两个灵活齿席夫碱配体，并与 Zn(II) 和 Cu(II) 盐反应。络合后，席夫碱在羟基处发生去质子化以充当单阴离子配体。当配体：金属比例为 2：1 时，去质子化的希夫碱通过酚盐和亚胺以方形平面或四面体几何结构配位金属离子。相比之下，5-氯水杨醛亚胺与金属离子以 1:1 的比例反应形成络合物，其中吗啉氮也参与 N,N,O-三齿配位模式。通过光谱方法和单晶X射线衍射表征了配合物的结构。

  DOI：

  10.1080/00958972.2012.708412

文献信息

• 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.
• Role of ligand backbone of tridentate Schiff-base on complex nuclearity and bio-relevant catalytic activities of zinc(II) complexes: Experimental and theoretical investigations
  作者：Prateeti Chakraborty、Jaydeep Adhikary、Ria Sanyal、Amitava Khan、Krishnendu Manna、Sanjit Dey、Ennio Zangrando、Antonio Bauzá、Antonio Frontera、Debasis Das

  DOI：10.1016/j.ica.2014.06.018

  日期：2014.9