1-(2-hydroxybenzyl)-1,5-diazacyclooctane | 300825-21-2

• 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: 1-(2-hydroxybenzyl)-1,5-diazacyclooctane
• 英文别名: 2-[(1,5-Diazocan-1-yl)methyl]phenol；2-(1,5-diazocan-1-ylmethyl)phenol
• CAS: 300825-21-2
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: AHXJUVHELSSWRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  35.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 1-(2-hydroxybenzyl)-1,5-diazacyclooctane 以 水 、 丙酮 为溶剂， 以52%的产率得到
  参考文献：
  名称：

  Novel copper(II) complexes with diazamesocyclic ligands functionalized by additional donor group(s): syntheses, crystal structures and magnetic properties

  摘要：

  基于 l,5-二氮杂环辛烷（DACO）的三种重氮杂环配体的铜（II）配合物带有额外的咪唑或苯酚功能供体基团，即 1,5-双（咪唑-4-基甲基）-（L111）、1-（咪唑-4-基甲基）-（L222）和 1-（2-羟基苄基）-1,5-二氮杂环辛烷（HL333）、1-(imidazol-4-ylmethyl)- (L222) 和 1-(2-羟基苄基)-1,5-二氮杂环辛烷 (HL333)，并通过 X 射线衍射分析确定了它们的结构。研究发现，L111 与 Cu(ClO4)2-6H2O 形成单核络合物 [CuL111Cl]ClO4-H2O 1，L222 形成 μ-Cl 桥双核络合物 [CuL222Cl]2[ClO4]22，而 HL333 则形成苯氧基桥双核络合物 [CuL33(H2O)]2[ClO4]23。这三种复合物中的每个 CuII 都是五配位的，处于畸变的方阵环境中。对于单核络合物 1，Cl-阴离子位于顶端位置，而对于μ-Cl-桥接双核络合物 2，两个桥接的 Cl-阴离子同时占据轴向和一个赤道位置，Cu-Cl-Cu 角为 88.在苯氧基桥联双核络合物 3 中，Cu-O-Cu 桥联角为 100.80(12)°，分子内 Cu ⋯ Cu 间距为 3.双核络合物 2 和 3 在 4.2-300 K 范围内的变温磁感应强度测量结果表明，双核铜(II)中心之间的分子内磁性耦合存在很大差异，从弱铁磁耦合到非常强的反铁磁耦合，2J = 1.16（2）与 -574 cm-1（3）之间的差异很大。通过紫外可见光/可见光和 ESR 技术进一步研究了这些复合物的溶液行为。

  DOI：

  10.1039/b007424l

文献信息

• Novel nickel(II) complexes with diazamesocyclic ligands functionalized by additional phenol donor pendant(s): synthesis, characterization, crystal structures and magnetic properties
  作者：Xian-He Bu、Miao Du、Lei Zhang、Dai-Zheng Liao、Jin-Kui Tang、Ruo-Hua Zhang、Mitsuhiko Shionoya

  DOI：10.1039/b008297j

  日期：——

  μ-phenoxo-bridged nickel(II) complexes with l,5-diazacyclooctane (DACO) ligands functionalized by additional phenol donor pendants has been achieved and the complexes have been characterized by IR, elemental analyses, conductivity, thermal analysis, and UV-Vis techniques. Single-crystal X-ray diffraction analyses reveal that HL111 forms a phenoxo-bridged binuclear complex (in the presence of N3− anions)

  与1,5-二氮杂环辛烷（DACO）形成的两个独特的μ-苯氧基桥联镍（II）配合物配体 通过附加功能 苯酚 供体的悬垂物已经实现，并且配合物的特征在于 红外，元素分析，电导率，热分析和 紫外可见 技术。 单晶X射线衍射分析表明，HL 1所11形成phenoxo桥连双核络合物（在N存在3 -阴离子）[镍大号1 11（N 3）] 2 ·0.5H 2 Ô 1，ħ 2 2L 2 2一个phenoxo桥接边缘共享线性三核络合物[Ni 3（L 2 2）2（C 2 H 5 OH）2 Cl 2 ] 2，其中HL 1 11  =1-（2-羟基苄基）-1,5-二氮环辛烷和H 2 2L 2 2  = 1,5-双（2-羟基苄基）-1,5-二氮杂环辛烷。在图1中，两个Ni II处于五配位畸变的方金字塔形环境中，分子内Ni ⋯ Ni距离为3.1232（13）Å。但是，在2中，两个末端Ni II处于几乎理想的方金字塔协调环境中，而中心Ni
• Varying Coordination Modes and Magnetic Properties of Copper(II) Complexes with Diazamesocyclic Ligands by Altering Additional Donor Pendants on 1,5-Diazacyclooctane
  作者：Xian-He Bu、Miao Du、Zhi-Liang Shang、Ruo-Hua Zhang、Dai-Zheng Liao、Mitsuhiko Shionoya、Thomas Clifford

  DOI：10.1021/ic000094d

  日期：2000.9.18

  nature of the pendant arms is a key factor governing the structure and properties of the complexes; therefore, the coordination modes and properties of the metal complexes of a diazamesocycle can be controlled by altering the pendant donors on it. Magneto-structural correlation has been precisely analyzed, and the solution properties of these complexes have also been described.

  基于二氮杂杂环1,5-二氮杂环辛烷（DACO）的一系列新的二氮杂杂环配体，由其他供体基团--1,5-双（N-1-甲基咪唑-2-基甲基）-1,5-二氮杂环辛烷（ L1），1-（2-羟基苄基）-1,5-二氮杂环辛烷（HL2），1,5-双（2-羟基苄基）-1,5-二氮杂环辛烷（H2L3）和1-（N-1-甲基咪唑-已合成并表征了2-ylmethyl）-1,5-diazacyclooctane（L4）及其Cu（II）配合物。四种Cu（II）配合物的单晶X射线衍射分析表明，L1形成五配位单核配合物，HL2形成N3μ桥接的双核配合物，H2L3形成氧μ桥接的三核配合物，L4形成一个Cu（II）的三维之字形配位聚合物络合物。[CuL1ClO4]（ClO4）（I）：a = 12.194（2）A，b = 13.351（3）A，c = 14.473（3）A，β= 107.10（3）度，Z =4。[CuL2（N3）
• Synthesis, spectral and structural characterization of a novel phenoxo-bridged dinuclear CoII complex with a tridentate phenol-functionalized diazamesocyclic ligand
  作者：Miao Du、Dao-Li An、Ya-Mei Guo、Xian-He Bu

  DOI：10.1016/s0022-2860(02)00321-6

  日期：2002.11

  A novel phenoxo-bridged dinuclear Co-II complex with a diazamesocyclic ligand bearing one additional phenol functional donor group, [CoLCl](2).2C(3)H(6)O (1) (where HL = 1-(2-hydroxybenzyl)-1,5-diazacyclooctane), has been synthesized and characterized by elemental analyses, conductance, thermal analyses, IR and UV-vis spectra. The crystal structure of complex 1 has been determined by X-ray diffraction technique, which reveals that it is a neutral complex and resides on a crystallographic inversion center. The two Coll centers bridged by the phenoxo groups are penta-coordinated, taking a coordination sphere in the midst of the ideal square-pyramid and trigonal bipyramid. 1,5-Diazacyclooctane of the ligand takes a boadchair conformation and an H atom from it effectively blocks the axial coordination site opposite the Cl- ligand to form CoN2O2Cl geometry. The crystal structure is stabilized by the N-H...O hydrogen bond between the amino group and the acetone molecule. C) 2002 Elsevier Science B.V. All rights reserved.
• Bis{μ-2-[(1,5-diaza-1-cyclooctyl)methyl]phenolato-<i>N</i>,<i>N</i>′,<i>O</i>:<i>O</i>}bis[chlorozinc(II)] diacetone solvate: design of a square-pyramidal ZnN₂O₂Cl complex
  作者：Qiang Xu、Miao Du、Ya-Mei Guo、Xian-He Bu

  DOI：10.1107/s0108270101007004

  日期：2001.8.15

  The title complex, [Zn-2(C13H19N2O)(2)Cl-2]. 2C(3)H(6)O, resides on a crystallographic inversion center. The two Zn-II centers bridged by the phenoxo groups are in pentacoordinated distorted square-pyramidal coordination environments with an intramolecular Zn . . . Zn distance of 3.175 (3) Angstrom. The mesocyclic ligand takes a boat-chair conformation and an H atom from the 1,5-diazacyclooctane ring effectively blocks the axial coordination site opposite the Cl ligand to form the ZnN2O2Cl geometry. The crystal structure is stabilized by a N-H . . .O hydrogen bond between the amino group and an acetone molecule.
• Novel copper(II) complexes with diazamesocyclic ligands functionalized by additional donor group(s): syntheses, crystal structures and magnetic properties
  作者：Xian-He Bu、Miao Du、Lei Zhang、Zhi-Liang Shang、Ruo-Hua Zhang、Mitsuhiko Shionoya

  DOI：10.1039/b007424l

  日期：——

  Copper(II) complexes with three diazamesocyclic ligands based on l,5-diazacyclooctane (DACO) bearing additional imidazole or phenol functional donor groups, 1,5-bis(imidazol-4-ylmethyl)- (L111), 1-(imidazol-4-ylmethyl)- (L222), and 1-(2-hydroxybenzyl)-1,5-diazacyclooctane (HL333), have been newly synthesized and characterized, and their structures determined by X-ray diffraction analyses. It has been revealed that with Cu(ClO4)2·6H2O L111 forms a mononuclear complex [CuL111Cl]ClO4·H2O 1, L222 forms a μ-Cl− bridged binuclear complex [CuL222Cl]2[ClO4]22, whereas HL333 forms a phenoxo-bridged binuclear complex [CuL33(H2O)]2[ClO4]23. Each CuII in the three complexes is five-coordinated in a distorted square-pyramidal environment. For the mononuclear complex 1 the Cl− anion is at the apical site, whereas for the μ-Cl−-bridged binuclear complex 2 the two bridging Cl− anions occupy both the axial and one equatorial position with Cu–Cl–Cu angle 88.81(5)° and intramolecular Cu ⋯ Cu separation 3.494(8) Å. In the phenoxo-bridged binuclear complex 3 the Cu–O–Cu bridging angle is 100.80(12)° and the intramolecular Cu ⋯ Cu distance is 3.0324(9) Å. Variable-temperature magnetic susceptibility measurements on the two binuclear complexes 2 and 3 in the range 4.2–300 K indicate a quite different magnetic intramolecular coupling between the binuclear copper(II) centers, from a weak ferromagnetic to a very strong antiferromagnetic coupling, with 2J = 1.16 (for 2) vs. −574 cm−1 (for 3), and the magneto-structural correlations are discussed in detail. The solution behaviors of the complexes have been further studied by UV/Vis and ESR techniques.

  基于 l,5-二氮杂环辛烷（DACO）的三种重氮杂环配体的铜（II）配合物带有额外的咪唑或苯酚功能供体基团，即 1,5-双（咪唑-4-基甲基）-（L111）、1-（咪唑-4-基甲基）-（L222）和 1-（2-羟基苄基）-1,5-二氮杂环辛烷（HL333）、1-(imidazol-4-ylmethyl)- (L222) 和 1-(2-羟基苄基)-1,5-二氮杂环辛烷 (HL333)，并通过 X 射线衍射分析确定了它们的结构。研究发现，L111 与 Cu(ClO4)2-6H2O 形成单核络合物 [CuL111Cl]ClO4-H2O 1，L222 形成 μ-Cl 桥双核络合物 [CuL222Cl]2[ClO4]22，而 HL333 则形成苯氧基桥双核络合物 [CuL33(H2O)]2[ClO4]23。这三种复合物中的每个 CuII 都是五配位的，处于畸变的方阵环境中。对于单核络合物 1，Cl-阴离子位于顶端位置，而对于μ-Cl-桥接双核络合物 2，两个桥接的 Cl-阴离子同时占据轴向和一个赤道位置，Cu-Cl-Cu 角为 88.在苯氧基桥联双核络合物 3 中，Cu-O-Cu 桥联角为 100.80(12)°，分子内 Cu ⋯ Cu 间距为 3.双核络合物 2 和 3 在 4.2-300 K 范围内的变温磁感应强度测量结果表明，双核铜(II)中心之间的分子内磁性耦合存在很大差异，从弱铁磁耦合到非常强的反铁磁耦合，2J = 1.16（2）与 -574 cm-1（3）之间的差异很大。通过紫外可见光/可见光和 ESR 技术进一步研究了这些复合物的溶液行为。