N,N'-bis(2,3-dihydroxybenzoyl)-1,4-phenylenediamine | 179469-22-8

• 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: N,N'-bis(2,3-dihydroxybenzoyl)-1,4-phenylenediamine
• 英文别名: 1,4-bis(2',3'-dihydroxybenzamido)phenylene；N,N'-1,4-Phenylenebis(2,3-dihydroxybenzamide)；N-[4-[(2,3-dihydroxybenzoyl)amino]phenyl]-2,3-dihydroxybenzamide
• CAS: 179469-22-8
• 化学式: C₂₀H₁₆N₂O₆
• 分子量: 380.357
• InChiKey: STOKWFCJMQAUHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2,3-dihydroxybenzoyl)-1,4-phenylenediamine 、 triethoxy[(2,2,6,6-tetramethylpiperidino)methyl]silane 以 甲醇 为溶剂， 反应 96.0h， 以41%的产率得到
  参考文献：
  名称：

  Self-assembled macrocycles with pentavalent silicon linkages

  摘要：

  Organic substrates containing two catechol (ortho-dihydroxybenzene) components at opposite ends self-assemble with a silicon substrate containing three nucleofugic groups (methoxy or ethoxy) under basic conditions to produce macrocycles ranging from monomers to pentamers. Silicon in all the macrocycles is pentacoordinate, negatively charged, and possessed of one organic monodentate ligand attached via carbon and two catechol bidentate ligands attached via oxygen. The organic materials with the two catechol structures thus serve as struts between the corners provided by the pentacoordinate silicon atoms. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.04.011
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 氯化亚砜 、 三溴化硼 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 N,N'-bis(2,3-dihydroxybenzoyl)-1,4-phenylenediamine
  参考文献：
  名称：

  用于电子介导的核量子模拟的双量子比特分子结构†

  摘要：

  高度相干的量子比特对之间的可切换交互是量子信息处理物理实现的关键因素。实现量子逻辑操作的一种有希望的途径涉及使用核自旋作为受保护的基本信息单元，即量子比特。在这里，我们提出了一种简单的方法，使用快速电子自旋激发来切换核自旋量子位之间的有效相互作用，并实现基于高度相干的钒基部分的双量子位分子结构来实现量子逻辑操作。通过电子自旋之间的化学调谐磁耦合，量子位之间的纠缠产生受控产生是可能的，钒的分裂清楚地证明了这一点（IV) 连续波电子顺磁共振谱中的超细线。该系统已通过脉冲电子顺磁共振光谱进一步表征，证明相干时间非常长。实验得出的自旋哈密顿参数已被用于模拟系统动力学，该参数在实现量子门所需的脉冲序列下进行现实描述，其中还包括退相干的有害影响。这证明了使用这种分子复合物来实现控制 Z (CZ) 门和简单的量子模拟的可能性。实际上，我们还提出了基于S = 1 自旋系统中磁化的量子隧穿模拟的原理验证实验。

  DOI：

  10.1039/c8sc01695j

文献信息

• [EN] IRON(III) AND GALLIUM(III) METAL ORGANIC POLYHEDRA, METHODS OF MAKING SAME, AND USES THEREOF<br/>[FR] POLYÈDRES ORGANIQUES MÉTALLIQUES DE FER(III) ET DE GALLIUM(III), LEURS PROCÉDÉS DE FABRICATION ET LEURS UTILISATIONS
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2020263761A1

  公开（公告）日：2020-12-30

  Compounds may have at least two structural units, which may be referred to as ligands. Each structural unit includes at least one spacer group and two or more donor groups. Compounds may have two or more iron(III) cations, one or more of which may be a high- spin iron(III) cation or high-spin iron(III) cations, two or more gallium(III) cations, or at least one iron(III) cation, one or more of which may be a high-spin iron(III) cation or high-spin iron(III) cations, and at least one gallium(III) cation, where the iron(III) cation(s) and/or the gallium(III) cation(s) coordinate to the donor groups. The compounds may be self-assembled cages. A composition may include one or more of the compound(s) and a pharmaceutically accepted carrier. Methods of imaging use one or more of the compound(s) and/or one or more of the composition(s).

  化合物可能至少有两个结构单元，可以称为配体。每个结构单元包括至少一个间隔基团和两个或更多供体基团。化合物可能具有两个或更多个铁（III）阳离子，其中一个或多个可能是高自旋铁（III）阳离子，两个或更多个镓（III）阳离子，或至少一个铁（III）阳离子，其中一个或多个可能是高自旋铁（III）阳离子，和至少一个镓（III）阳离子，其中铁（III）阳离子和/或镓（III）阳离子与供体基团配位。这些化合物可能是自组装笼状结构。一种组合物可能包括一个或多个这些化合物和一个药用可接受的载体。成像方法使用一个或多个这些化合物和/或一个或多个这些组合物。
• Supramolecular Asymmetric Induction in Dinuclear Triple-Stranded Helicates¹
  作者：Robert M. Yeh、Kenneth N. Raymond

  DOI：10.1021/ic0515711

  日期：2006.2.1

  Supramolecular chiral induction has been observed in five dinuclear triple-stranded helicates composed entirely of achiral components. Three different chiral cations were found to be very effective at inducing high levels of enantiomeric enrichment in racemic mixtures of the helicates. The mechanism of intermolecular chiral induction in one cation-helicate pair, s-nic/K6[Ga2L(1)3], has been elucidated

  在完全由非手性组分组成的五个双核三链螺旋物中观察到超分子手性诱导。发现三种不同的手性阳离子对于在螺旋产物的外消旋混合物中诱导高水平的对映异构体富集非常有效。通过圆二色谱，X射线晶体学以及一维和二维NMR光谱（s- nic = N-甲基-s-烟碱，H4L（1）= 1,4-双（2'，3'-二羟基苯甲酰胺基）亚苯基）。
• Superamolecular Self-Recognition and Self-Assembly in Gallium(III) Catecholamide Triple Helices
  作者：Dana L. Caulder、Kenneth N. Raymond

  DOI：10.1002/anie.199714401

  日期：1997.8.4
• Rearrangement Reactions in Dinuclear Triple Helicates¹
  作者：Michel Meyer、Berthold Kersting、Ryan E. Powers、Kenneth N. Raymond

  DOI：10.1021/ic970864u

  日期：1997.11.1

  A series of dinuclear M(III) (M = Fe or Ga) catecholate complexes has been prepared using bisbidentate catecholate ligands (L). The products contain discrete, dinuclear M-2(L)(3)(6-) anions featuring pseudo-octahedral coordination centers. The helical nature of the dinuclear complexes has been established by CD spectroscopy and X-ray crystallography. The salt (N(CH3)(4))(6)Ga-2(L-3)(3) (L-3 = N,N'-bis(2,3-dihydroxy-4-carbamoylbenzoyl)-1,4-phenylene-diamine) has been characterized by X-ray diffraction; crystals are hexagonal, space group with unit cell dimensions a = 14.283(2) Angstrom, c = 42.966(2) Angstrom, V = 7591 Angstrom(3), and Z = 2. Variable-temperature H-1 NMR experiments demonstrate that the configuration inversion of the enantiomers of K6Ga2(L-4)(3) (L-4 = N,N-bis(2,3-dihydroxy-4-(isopropylcarbamoyl)benzoyl) 1,4-phenylenediamine) and K6Ga2(L-5)(3) (L-5 = N-(2,3-dihydroxy-4-(isopropylcarbamoyl)benzoyl)-N'-(2,3-dimethoxy-4-(methylcarbamoyl)benzoyl)-1,4-phenylenediamine) is facile in D2O Or DMSO-d(6). The mechanism of inversion has been probed by dynamic NMR spectroscopy, using the complex K6Ga2(L-5)(3) which exists in two isomeric forms in solution, cis- and trans. The intramolecular inversion of the dinuclear helicates occurs without cis-trans isomerization and proceeds by independent trigonal twisting of each metal center, affording the heterochiral meso complex as an intermediate. The free energy of activation for the inversion of K6Ga2(L-4)(3) in D2O at p[D] = 12.1 is Delta G(298)(double dagger) = 79(2) kJ mol(-1), with Delta H = 75(2) kJ mol(-1) and Delta S-double dagger = -12(6) J mol(-1) K-1. Under slightly acidic conditions a proton-assisted pathway becomes dominant and the rate of inversion shows a second-order dependence in [D+]. The heterochiral meso complex of Ga-2(L-4)(6)(3-) is shown to be a transient kinetic intermediate in the (Lambda,Lambda) <-> (Delta,Delta) inversion process of the helicate complex.
• Synthesis and characterization of a novel macrocyclic ligand containing catechol donor groups and its oxovanadium(IV) complex
  作者：Tingli Ma、Takahiko Kojima、Yoshihisa Matsuda

  DOI：10.1016/s0277-5387(00)00387-9

  日期：2000.5

  A novel macrocyclic ligand containing catechol moieties, 9,10,21,22-tehrahydroxy-7,12,19,24-tetraoxo-2,3,4,5:8,9,10,11:14,15,16, 17:20,21,22,23-tetrabenzena-1,6,13,18-tctraazacyclotetracosane (H4L), was designed and synthesized. For comparison, an acyclic ligand, 1,4-bis(2,3-dihydroxybenzammido)benzene (H4La), was also synthesized. Their oxovanadium(IV) complexes K(ppn)[VO(L)] and K-2[VO(L-a)] were prepared and characterized by IR, UV-Vis and ESR spectroscopies. The ESR spectra of the complexes measured at 77 K in diethyl sulfoxide-ethanol revealed unusual rhombic characteristics of the complexes, suggesting the coordination geometry of the complexes was distorted square-pyramidal. Based on these data, the complex is proposed to possess a bowl-like structure capped by the VO2+ moiety with a hydrophobic cavity. (C) 2000 Elsevier Science Ltd All rights reserved.