3,3'-bis(2-hydroxybenzaldehyde) | 121073-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3'-bis(2-hydroxybenzaldehyde)
• 英文别名: 3,3'-(3-oxapentane-1,5-diyldioxy)bis(2-hydroxybenzaldehyde)；3,3'-(3-oxopentane-1,5-diyldioxy)bis(2-hydroxybenzaldehyde)；3,3'-[Oxybis(2,1-ethanediyloxy)]bis(2-hydroxybenzaldehyde)；3,3'-(3-Oxapentan-1,5-diyldioxy)bis(2-hydroxybenzaldehyde)；3-[2-[2-(3-formyl-2-hydroxyphenoxy)ethoxy]ethoxy]-2-hydroxybenzaldehyde
• CAS: 121073-78-7
• 化学式: C₁₈H₁₈O₇
• 分子量: 346.337
• InChiKey: KPTPRBUPWWBWGN-UHFFFAOYSA-N

物化性质

• 熔点：
  62 °C
• 沸点：
  518.9±50.0 °C(Predicted)
• 密度：
  1.342±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,3'-bis(2-hydroxybenzaldehyde) 在 triethylamine 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  d-或f-单核和相关异双核配合物与 [1+1] 不对称室大环

  摘要：

  d-或 f-单核和 d,f-异双核配合物与 [1+1] 不对称隔室大环 H2LA、H2LB、H2LC 或 H2LD，衍生自 1,2-二氨基乙烷或 1,3-二氨基丙烷与 3,已经合成并表征了 3'-(3-oxapentane-1,5-diyldioxy)bis(2-hydroxybenzaldehyde) 或 3,3'-(3,6dioxactane-1,8-diyldioxy)bis(2-hydroxybenzaldehyde)，包括通过单晶 X 射线结构测定。还测试了配位大小和相邻两个室的供体原子数对稳定 d,f-异双核配合物制备的影响。同构配合物 [MLn(L)(Cl)3(CH3OH)] (MLn = LaCu, LaZn, TbCu) 的 X 射线结构显示金属（II）离子以方锥配位存在于 N2O2 位点中，第五根尖位置被氯离子填充，而每个镧系元素 (III) 离子位于 O2O4 位点，

  DOI：

  10.1002/ejic.200400135
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 、 二乙二醇双对甲苯磺酸酯 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以49%的产率得到3,3'-bis(2-hydroxybenzaldehyde)
  参考文献：
  名称：

  Macrocyclic trinucleating ligands for the cocomplexation of two "soft" (Cu2+, Ni2+, or Zn2+) metal centers and one "hard" (Ba2+ or Cs+) metal center

  摘要：

  Macrocyclic heterotrinucleating ligands that have one compartment for complexation of alkaline or alkaline earth cations and two compartments for transition-metal cations have been synthesized. The Ba2+-templated (2 + 2) macrocyclization of the dialdehydes 3a and 3b with the diamine 8 yielded the barium complexes (9b, 9e) in high yield. The Cs+-templated (2 + 2) macrocyclization of the dialdehyde 3a and the diamine 8 gave the cesium complex 9c. The mononuclear complexes were converted into the heterotrinuclear complexes 10a-h by reaction with 2 equiv of copper, nickel, or zinc acetate. The barium complex 9b, the dicopper/barium complex 10a, and the dinickel/barium complex 10b have been analyzed by X-ray crystallography. In all three crystal structures the O10 cavity is folded around the barium cation. The copper-copper distance in the dicopper/barium complex 10a is 3.50 angstrom and the nickel-nickel distance in the dinickel/barium complex 10b is 3.42 angstrom. The electrochemistry of the copper-containing heterotrinuclear complexes 10a, 10d, and 10g and the nickel-containing heterotrinuclear complexes 10b, 10e, and 10h has been studied by polarography, cyclic voltammetry, and coulometry in DMSO. The dinickel/barium complex 10b was also studied by Kalousek polarography. The dicopper/metal complexes 10a, 10d, and 10g all show a copper-copper interaction, which is the strongest for the dicopper/barium complex 10a. Coulometry revealed that the complexes 10a, 10d, and 10g undergo a reduction with two electrons, and cyclic voltammetry showed that the reduction/oxidation processes of 10a, 10d, and 10g are chemically reversible. The reduction/oxidation processes of the nickel-containing heterotrinuclear complexes 10b, 10e, and 10h are complicated by adsorption phenomena. Frozen EPR spectra of 10a and 10g exhibit typical triplet spectra with a zero-field splitting of about 0.04 cm-1. This behavior is typical for Cu(II) dimers and confirms that both Cu(II) cations are also exchange coupled in solution. A Cu-Cu distance in solution of 3.6 angstrom agrees best with the spectra. Attempts to add exogenous bridging ligands like F- and imidazolate were unsuccessful.

  DOI：

  10.1021/jo00001a043

文献信息

• [1+1] Asymmetric Compartmental Macrocycles Bearing a Pendant Arm and Related <i>s,f</i> ‐Heterodinuclear Complexes Containing Lanthanide( <scp>III</scp> ) and Sodium Ions
  作者：Sergio Tamburini、Umberto Casellato、Laura Bertolo、Pietro Alessandro Vigato

  DOI：10.1002/ejic.200400955

  日期：2005.6

  It was found that the lanthanide(III) ion resides in the N3XO2 chamber while the sodium(I) ion fills the O2O3 crown-ether-like chamber, as ascertained for the complex [DyNa(LC)(PrOH)(Cl)] by a single-crystal X-ray structural investigation. The complex is monoclinic, space group P21/c, with a = 9.601(2), b = 12.927(2), c = 26.638(4) A, β = 99.55(3)°. The dysprosium ion is seven-coordinate in the N3O2

  [1+1] 报告了不对称隔室大环和/或相关的单核、同双核和钠 (I)-镧系元素 (III) 异双核配合物，并通过 SEM-EDS 显微镜和 1H、13C 和 23Na NMR 光谱研究了它们的性质。这些配体带有一个悬臂，由 -CH2COOH (H3LA)、-CH2C5H4N (H2LB) 或 -CH2C6H4OH (H3LC) 基团与氨基氮键合表示，并包含一个 O2O3 冠醚样室和一个 N3XO2（其中 X = O, N) 席夫碱室。发现镧系元素 (III) 离子驻留在 N3XO2 室中，而钠 (I) 离子填充 O2O3 冠醚样室，如复合物 [DyNa(LC)(PrOH)(Cl)] 所确定的那样单晶 X 射线结构研究。该配合物为单斜晶系，空间群 P21/c，a = 9.601(2), b = 12.927(2), c = 26.638(4) A, β = 99.55(3)°。镝离子在 N3O2
• Phosphorylated Hydrazines and Aldehydes as Precursors of Phosphorus-Containing Multimacrocycles
  作者：Joeelle Mitjaville、Anne-Marie Caminade、Jean-Claude Daran、Bruno Donnadieu、Jean-Pierre Majoral

  DOI：10.1021/ja00111a007

  日期：1995.2

  afforded another type of bimacrocyclic species, 20, containing five phosphorus atoms. A Staudinger reaction between the phosphine 22 bearing a crown ether unit and the diazido tetraphosphorus-containing macrocycle 21 led to a trimacrocycle, 24, possessing one central phosphorus macrocycle and two crown ethers. Similarly the reaction between phosphine 22 (4 equiv) with the tetraazido tetraphosphorus-containing

  提供了另一种类型的双大环物质，20，含有五个磷原子。带有冠醚单元的膦 22 与含二叠氮基四磷的大环 21 之间的施陶丁格反应产生了三大环 24，它具有一个中心磷大环和两个冠醚。类似地，膦 22（4 当量）与含四叠氮基四磷的大环 25 之间的反应得到五大环物质 27。（1）R 3。双大环 15a、b 可以通过二醛 7 与三酰肼（Y）P[N 反应获得(CH3)- 具有一个中心磷大环和两个冠醚。类似地，膦 22（4 当量）与含四叠氮基四磷的大环 25 之间的反应得到五大环物质 27。（1）R 3。双大环 15a、b 可以通过二醛 7 与三酰肼（Y）P[N 反应获得( )- 具有一个中心磷大环和两个冠醚。类似地，膦 22（4 当量）与含四叠氮基四磷的大环 25 之间的反应得到五大环物质 27。（1）R 3。双大环 15a、b 可以通过二醛 7 与三酰肼（Y）P[N 反应获得( )-
• Spectroscopy, NMR and DFT studies on molecular recognition of crown ether bridged chiral heterotrinuclear salen Zn(II) complex
  作者：Feng Gao、Wen-Juan Ruan、Jia-Mei Chen、Ying-Hui Zhang、Zhi-Ang Zhu

  DOI：10.1016/j.saa.2005.03.021

  日期：2005.12

  BaZn2L(ClO4)2-DABCO supramolecular assembly was specially studied via 1H NMR titration and 1H ROESY. To understand the recognition on molecular level, density functional theory (DFT) calculations on B3LYP/LanL2DZ were performed on the minimal energy conformations of host, guests, and host-guest complexes. The minimal energy conformations were obtained by molecular mechanics (MM) optimization and molecular

  合成了含钡的冠醚桥联手性异核萨伦Zn（II）配合物BaZn2L（ClO4）2，其中L是折叠的双核手性（R，R）-salen配体，并通过元素分析，1H NMR，UV表征-vis，IR，圆二色性（CD）光谱和质谱。作为折叠的双核手性宿主，通过以下方法研究了其对非手性客体（咪唑衍生物），刚性双齿客体（1,4-重氮双环[2,2,2]辛烷，DABCO）和手性客体（氨基酸甲酯）的识别紫外可见分光光度滴定，CD光谱。发现D-氨基酸甲酯的缔合常数高于其L-对映异构体的缔合常数。通过1H NMR滴定和1H ROESY对BaZn2L（ ）2-DABCO超分子组装体的三明治型结合进行了研究。为了了解分子水平上的识别，对B3LYP / LanL2DZ的密度泛函理论（DFT）计算是基于宿主，客体和宿主-客体复合物的最小能量构象进行的。通过分子力学（MM）优化和分子动力学（MD）模拟获得了最小的能量构象。分析了
• Cyclic and acyclic compartmental Schiff bases, their reduced analogues and related mononuclear and heterodinuclear complexes
  作者：U. Casellato、S. Tamburini、P. Tomasin、P.A. Vigato

  DOI：10.1016/j.ica.2004.06.007

  日期：2004.11

  metal ion. The Schiff bases H2L have been reduced by NaBH4 to the related polyamine derivatives H2R, which form, when reacted with the appropriate metal ions, M(H2R)(X)2 (M= Co2+, Ni2+; X=CH3COO−, Cl−), Cu(R) · nH2O and Mn(R)(CH3COO) · nH2O. The prepared ligands and related complexes have been characterized by IR, NMR and mass spectrometry. The [1+1] cyclic nature of the macrocyclic polyamine systems

  [1 + 1]个大环和[1 + 2]个大环隔室配体（H 2 L），包含一个N 2 O 2，N 3 O 2，N 2 O 3，N 4 O 2或O 2 N 2 O 2 Schiff通过适当缩合的甲酰基和胺前体的自缩合制备了一个碱基位点和一个O 2 O n（n = 3，4）冠醚样位点。在钠离子存在下的模板程序提供Na 2（L）或Na（HL）·  n H 2O.与适当的过渡金属乙酸盐水合物反应时，H 2 L形成M（L）·  n H 2 O，M（HL）（CH 3 COO）·  n H 2 O，M（H 2 L）（X）2  ·  ñ ħ 2 O（M =铜2+，钴2+，镍2+ ; X = CH 3 COO - ，氯- ）或Mn（L）（CH 3 COO）·  ñ ħ 2O根据所用实验条件而定。在所需的金属离子存在下，通过缩合适当的前体制备了相同的配合物。Schiff碱H 2 L已被NaBH 4还原为相关的多胺衍生物H
• Synthesis and reactivity of Ln- and LnNa-macrocyclic compartmental Schiff base and polyamino complexes
  作者：Valentina Peruzzo、Arianna Lanza、Fabrizio Nestola、Pietro Alessandro Vigato、Sergio Tamburini

  DOI：10.1016/j.ica.2014.03.032

  日期：2014.5

  heterodinuclear-LnNa complexes. The crystal structure of [LuNa(RB)(OH)]2, determined by single-crystal X-ray diffraction, indicates the preference of the lutetium(III) ion and of the sodium(I) ion for the Schiff base and the crown-ether like chambers, respectively. To test the flexibility of reduced ligands and the possibility to encapsulate different lanthanide(III) ions in the coordinating moiety, [LuNa

  摘要[1 + 1] Schiff碱大环配体H2LA和H3LB是由3,3'-（3-氧杂戊烷-1,5-二基二氧基）双（2-羟基苯甲醛）（H2L'）与1,5-缩合合成的二氨基-3-氮杂甲基戊烷（A'）和N，N-双（2-氨基乙基）-2-羟基苄胺·3HCl（HB'·3HCl）以及它们相关的多胺H2RA和H3RB，它们对水解和水解的稳定性增强。更大的灵活性产生了一系列单Ln和异双核LnNa复合物。通过单晶X射线衍射确定的[LuNa（RB）（OH）] 2的晶体结构表明the（III）离子和钠（I）离子对席夫碱和冠的偏爱-分别像腔室。为了测试还原的配体的柔韧性以及将不同的镧系元素（III）离子包封在配位部分中的可能性，[LuNa（RB）（CH3COO）]·2iPrOH，[LuNa（LB）（Cl）]，[LANa（RB）（Cl）]和[LANa（LB）（Cl）]与不同的镧系元素（III）盐混合通过ESI质谱和N