1,2,4,5-cyclohexanetetracarboxylic acid | 624286-71-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,4,5-cyclohexanetetracarboxylic acid
• 英文别名: cyclohexane-1e,2a,4a,5e-tetracarboxylic acid；cis,cis,cis-1,2,4,5-Cyclohexanetetracarboxylic acid；(1R,2S,4R,5S)-cyclohexane-1,2,4,5-tetracarboxylic acid
• CAS: 624286-71-1
• 化学式: C₁₀H₁₂O₈
• 分子量: 260.2
• InChiKey: ZPAKUZKMGJJMAA-GUCUJZIJSA-N

物化性质

• 沸点：
  549.1±50.0 °C(Predicted)
• 密度：
  1.673±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2,4,5-cyclohexanetetracarboxylic acid 在 乙酸酐 作用下， 生成 cis,cis,cis-1,2:4,5-cyclohexanetetracarboxylic dianhydride
  参考文献：
  名称：

  cis,cis,cis-1,2,4,5-Cyclohexanetetracarboxylic acid and its dianhydride

  摘要：

  cis,cis,cis-1,2,4,5-Cyclohexanetetracarboxylic acid,C10H12O8, (I), contains a mirror plane and the cyclohexane ring exhibits a chair conformation. Two crystallographically independent hydrogen bonds form R-2(2)(14), R-2(2)(16) and R-4(4)(16) ring motifs, and propagation of these two hydrogen bonds along the c and b axes generates C-2(2)(16) and C-2(2)(7) chains. cis, cis, cis-1,2: 4,5-Cyclohexanetetracarboxylic dianhydride, C10H8O6, (II), was prepared by the reaction of (I) with acetic anhydride. The cyclohexane ring of (II) exhibits a boat conformation and the dihedral angle between the two anhydro rings is 117.5 (1)degrees.

  DOI：

  10.1107/s0108270103013362
• 作为产物：
  描述：

  均苯四甲酸二酐 在 Ru-carbon tetrabutoxytitanium 、 硫酸 、 氢气 作用下， 以 水 为溶剂， 149.85 ℃ 、5.0 MPa 条件下， 生成 1,2,4,5-cyclohexanetetracarboxylic acid
  参考文献：
  名称：

  cis,cis,cis-1,2,4,5-Cyclohexanetetracarboxylic acid and its dianhydride

  摘要：

  cis,cis,cis-1,2,4,5-Cyclohexanetetracarboxylic acid,C10H12O8, (I), contains a mirror plane and the cyclohexane ring exhibits a chair conformation. Two crystallographically independent hydrogen bonds form R-2(2)(14), R-2(2)(16) and R-4(4)(16) ring motifs, and propagation of these two hydrogen bonds along the c and b axes generates C-2(2)(16) and C-2(2)(7) chains. cis, cis, cis-1,2: 4,5-Cyclohexanetetracarboxylic dianhydride, C10H8O6, (II), was prepared by the reaction of (I) with acetic anhydride. The cyclohexane ring of (II) exhibits a boat conformation and the dihedral angle between the two anhydro rings is 117.5 (1)degrees.

  DOI：

  10.1107/s0108270103013362

文献信息

• Two Co(II) coordination polymers: treatment activity on CVB3 induced viral myocarditis
  作者：Ni Xu、Chun-Min Jia、Hui-Su Xia、Nan-Shan Chen、Zhi-Hua Zhan、Cai-Hong Li

  DOI：10.1080/24701556.2021.1956960

  日期：——

  present study, two new Co(II)-based coordination polymers with the chemical formulae of [Co2(chtc)(H2O)]·3H2O (1) and [Co2(chtc)(4,4′-bpy)0.5] (2) have been successfully prepared via a solvothermal reaction of Co(NO3)2·6H2O and cyclohexane-1e,2a,4a,5e-tetracarboxylic acid (H4chtc) without or with the auxiliary N-donor ligand 4,4′-bipyridine (4,4′-bpy). The as-prepared two coordination polymers have been

  摘要 在本研究中，两种新的 Co(II) 基配位聚合物的化学式为 [Co 2 (chtc)(H 2 O)]·3H 2 O ( 1 ) 和 [Co 2 (chtc)(4,4 '-bpy) 0.5 ] ( 2 ) 通过 Co(NO 3 ) 2 ·6H 2 O 与环己烷-1 e ,2 a ,4 a ,5 e-四羧酸 (H 4chtc) 没有或有辅助 N 供体配体 4,4'-联吡啶 (4,4'-bpy)。通过红外光谱、元素分析、热重分析、粉末 X 射线衍射研究和单晶 X 射线衍射分析研究了所制备的两种配位聚合物。此外，在体内评价了化合物1和2对CVB3诱导的病毒性心肌炎的治疗效果并探索了具体机制。肌酸激酶检测试剂盒用于检测心肌细胞中肌酸激酶（CK-MB）的含量。此外，进行实时逆转录-聚合酶链反应，测定心肌细胞中NF-κB的相对表达水平。
• Syntheses, Structures, Magnetic Properties, and NIR Emission Properties of a Series of Novel 1, 2, 4, 5-Cyclohexanetetracarboxylate-bridged Lanthanide Complexes with 3D Framework Structures
  作者：Li Wang、Wen Gu、Sheng-Yun Liao、Ming Zhang、Lin-Yan Yang、Xiao-Hua Wei、Xin Liu

  DOI：10.1002/zaac.201200144

  日期：2012.8.29

  Solvothermal combination of trivalent lanthanide metal precursors with 1, 2, 4, 5-cyclohexanetetracarboxylic acid (L) ligand has afforded the preparation of a family of eight new coordination polymers [Ln4(L)3(H2O)10]·7H2O (Ln = Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb) (1–8). Structural analyses reveal that the 1, 2, 4, 5-cyclohexanetetracarboxylic acid ligand with e,a,a,e (LI) conformation displays a μ4-(κ3O

  三价镧系金属前驱体与 1, 2, 4, 5-环己烷四甲酸 (L) 配体的溶剂热组合制备了八种新型配位聚合物 [Ln4(L)3(H2O)10]·7H2O (Ln = Eu、Gd、Tb、Dy、Ho、Er、Tm、Yb) (1-8)。结构分析表明，具有 e,a,a,e (LI) 构象的 1, 2, 4, 5-环己烷四甲酸配体显示出 μ4-(κ3O, O, O5)(κ2O2,O2)(κ2O4,O4)-生成复合体 1-8 的 3D 框架的桥接模式和具有短 Schlafli 符号 412.63} 的 α-Po 拓扑结构可以在复合体 1-8 中观察到。研究了近红外发光特性，结果表明HoIII、ErIII和YbIII配合物在固态下发出典型的近红外发光。配合物 2-7 的变温磁化率测量表明配合物 2 (Gd) 显示磁中心之间的铁磁耦合，而配合物 3-7 显示磁中心之间的反铁磁耦合。此外，还讨论了热重分析。
• Co(II)-coordination polymer: treatment and testing values on calculus of ureter by inhibiting the growth of urinary tract pathogens
  作者：Tao Yue、Yan Jing、Lei Tan、Rui Xue

  DOI：10.1080/24701556.2021.1952235

  日期：2022.5.4

  (2022). Co(II)-coordination polymer: treatment and testing values on calculus of ureter by inhibiting the growth of urinary tract pathogens. Inorganic and Nano-Metal Chemistry: Vol. 52, No. 5, pp. 693-698.

  （2022 年）。Co(II)-配位聚合物：抑制泌尿道病原体生长对输尿管结石的治疗及检测价值。无机和纳米金属化学：卷。52，第 5 期，第 693-698 页。
• A new Cu(II)-based coordination polymer: treatment activity on the glomerulonephritis via inhibiting the mesangial cell proliferation
  作者：Zheng Ye、Jingjing Xue、Jing Li、Xijing Wang、Fang Xu、Songlin Tan

  DOI：10.1007/s13738-020-02130-7

  日期：2021.7

  Through applying the mixed-ligand method, a new coordination polymer (CP) of Cu(II) with the chemical formula of Cu5(L)2(1,4-bimb)(μ3-OH)2(H2O)8]·2H2O}n (1, 1,4-bimb = 1,4-bis(imidazol-1-ylmethyl)benzene and H4L = 1,2,4,5-cyclohexanetetracarboxylic acid) was synthesized under the solvothermal conditions. Furthermore, the biological effect of compound against glomerulonephritis therapy was detected, and the details mechanism was investigated. First of all, the mesangial cells proliferation was detected through using the Cell Counting Kit-8 (CCK-8) method. Then, the Annexin V-FITC/PI method was utilized to determine cell cycle arrest and the apoptosis rate. Next, the caspase-8 and caspase-3 expression level in mesangial cells was detected via applying the western blot method. Finally, the inflammatory cytokines released into the plasma was assessed by ELISA detection kit.

  通过混合配体法，在溶热条件下合成了一种新的Cu(II)配位聚合物（CP），其化学式为Cu5(L)2(1,4-bimb)(μ3-OH)2(H2O)8]-2H2O}n（1, 1,4-bimb = 1,4-双(咪唑-1-基甲基)苯，H4L = 1,2,4,5-环己烷四羧酸）。此外，还检测了该化合物对肾小球肾炎治疗的生物效应，并对其详细机制进行了研究。首先，使用细胞计数试剂盒-8（CCK-8）法检测系膜细胞的增殖情况。然后，利用Annexin V-FITC/PI方法测定细胞周期停滞和细胞凋亡率。然后，采用 Western 印迹法检测间质细胞中 caspase-8 和 caspase-3 的表达水平。最后，通过 ELISA 检测试剂盒评估了释放到血浆中的炎症细胞因子。
• Two new 1,2,4,5-cyclohexanetetracarboxylate-bridged frameworks with metal hydroxide subunits. Synthesis, structures, magnetism and adsorption
  作者：Yong-Cong Ou、Jing Wang、Ji-Dong Leng、Zhuo-Jia Lin、Ming-Liang Tong

  DOI：10.1039/c0dt01497d

  日期：——

  The hydrothermal synthesis, X-ray crystal structures and thermal and magnetic properties of a layered coordination polymer, [Ni3.9Mn1.1(μ3-OH)2(LI)2(H2O)10]·2H2O (1) (LI = 1e,2a,4a,5e-cyclohexanetetracarboxylate), and a porous 3D coordination polymer, [Ni4(μ2-OH)2(μ6-H2LIV)2(pymc)(4,4′-bpy)(H2O)2](OH)·9H2O (2) (pymc = 2-pyrimidinecarboxylate, 4,4′-bpy = 4,4′-bipyridine, LIV = 1e,2e,4e,5e-cyclohexanetetracarboxylate), are reported in this paper. The structure of 1 has packed separated layers, each layer being formed of M3(μ3-OH)2 chains bridged by M(LI)2viahydrogen bonds. The magnetic properties are characterized by Néel transitions to fully compensated antiferromagnets at 2.9 K and show that 1 is a metamagnet resulting from the ferrimagnetic M3(μ3-OH)2 chains and other two metal atoms. Complex 2 is a 3D microporous coordination framework with 2D channels. The conformation of the 1,2,4,5-cyclohexanetetracarboxylate ligands (H4L) of complex 2 changes from LI (e,a,a,e) to LIV (e,e,e,e). The magnetic measurement indicates spin-canted antiferromagnetic behaviour, and the adsorption measurements show that 2 can selectively adsorb CO2 gas over N2 gas.

  一种层状配位聚合物[Ni3.9Mn1.1(μ3-OH)2(LI)2(H2O)10]-2H2O(1)（LI = 1e,2a,4a,5e-环己烷四甲酸酯）和多孔三维配位聚合物[Ni4(μ2-OH)2(μ6-H2LIV)2(PYMC)(4、4′-bpy)(H2O)2](OH)-9H2O（2）（PYMC = 2-嘧啶甲酸酯，4,4′-bpy = 4,4′-联吡啶，LIV = 1e,2e,4e,5e-环己烷四甲酸酯）。1 的结构具有密集的分离层，每一层都是由 M3(μ3-OH)2 链和 M(LI)2 通过氢键桥接而成。其磁性特征是在 2.9 K 时发生内耳跃迁，形成完全补偿的反铁磁体，这表明 1 是由铁磁性 M3(μ3-OH)2 链和其他两个金属原子形成的元磁体。配合物 2 是一个具有二维通道的三维微孔配位框架。配合物 2 中 1,2,4,5-Cyclohexanetetracarboxylate 配体 (H4L) 的构象从 LI（e,a,a,e）变为 LIV（e,e,e,e,e）。磁性测量结果表明，复合物 2 具有自旋倾斜的反铁磁性，而吸附测量结果表明，复合物 2 可以选择性地吸附二氧化碳气体而不是 N2 气体。