2,2'-bisbenzaldehyde | 76124-48-6

• 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: 2,2'-bisbenzaldehyde
• 英文别名: 1,3-bis(2-formylphenylthio)propane；1,5-bis(2-formylphenyl)-1,5-dithiapentane；1,3-di(2-formylphenylthio)propane；1,3-bis-(2-formyl-phenmylmercapto)propane；1,5-Bis(2-formylphenyl)-1,5-di-thiapentane；2-[3-(2-formylphenyl)sulfanylpropylsulfanyl]benzaldehyde
• CAS: 76124-48-6
• 化学式: C₁₇H₁₆O₂S₂
• 分子量: 316.445
• InChiKey: SZKJQIGKJKKCLN-UHFFFAOYSA-N

物化性质

• 熔点：
  51-53 °C(Solv: ethanol (64-17-5))
• 沸点：
  486.2±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-bisbenzaldehyde 在 sodium tetrahydroborate 、 silica gel 作用下， 以 水 为溶剂， 以85%的产率得到1,5-bis(2-hydroxybenzyl)-1,5-dithiapentane
  参考文献：
  名称：

  含15元S 4供体大环部分的新型金属卟啉的合成，表征和计算研究

  摘要：

  在该研究中，根据文献已经以高收率进行了1,5-双（2-甲酰基苯基）-1,5-二硫杂戊烷（3）的改进合成。通过前体化合物在无溶剂条件下的高产率还原反应，制备了1,5-双（2-苄醇）-1,5-二硫代戊烷（4）。在NaI存在下，在无水乙腈中用溴代三甲基硅烷处理取代的苄醇，以很高的收率形成了所需的碘衍生物（5）。通过化合物的反应合成了7,8-dihydro-6 H，14 H，19 H -dibenzo [ bj ] [1,12,5,8] tetradithiacyclopentadecine-16,17-dicarbonitrile（7）7和二硫代马来腈二钠盐。根据Linstead方法，在丁醇镁的存在下，通过二碳碳杂腈化合物（7）的环四聚反应，合成了对称地带有四个15元四硫杂四环大环的四氮杂卟啉镁。我们通过使用具有6-31G（d）基集的B3LYP方法，重点研究了化合物的几何优化，正模频率，UV吸收

  DOI：

  10.1016/j.tet.2016.09.028
• 作为产物：
  描述：

  1,3-bis-(2-hydroxymethylphenylthio)propane 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 生成 2,2'-bisbenzaldehyde
  参考文献：
  名称：

  The structural and electrochemical consequences of hydrogenating copper N2S2 Schiff base macrocycles

  摘要：

  A series of cis and trans tetradentate copper macrocyclic complexes, of ring size 14-16, that employ amine and thioether donor groups are reported. Apart from 5,6,15,16-bisbenzo-8,13-diaza-1,4-dithiacyclohexadecane copper(I) (cis-[Cu(H4NbuSen)](+)) all of the complexes are obtained in the copper(II) form. Crystallographic analysis shows that the copper(II) complexes all adopt a distorted planar geometry around the copper. In contrast, cis-[Cu(H4NbuSen)](+) is found to adopt a distorted tetrahedral geometry. The complexes were subjected to electrochemical analysis in water and acetonitrile. The effect of the solvent, positions of the donor atoms (cis/trans) on E-1/2 is discussed as is the comparison of the electrochemical behaviour of these complexes with their parent Schiff base macrocycles. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.01.012

文献信息

• Facile and Mild Displacement of Nitrite Ions in Electron-Deficient Nitroarenes by Alkyl or Aryl Thiols in the Presence of Magnesium Methoxide as a Solid Base Catalyst
  作者：Hossein Naeimi、Mohsen Moradian

  DOI：10.1055/s-0032-1317079

  日期：——

  The nucleophilic aromatic substitution reaction (S N Ar) between nitroarenes (having electron-withdrawing groups in the ­ortho or para position), and alkyl- or arylthiols using magnesium methoxide as a solid base catalyst is described. This method leads to the creation of a series of valuable compounds from arylsulfides via nucleophilic displacement of the nitro group with the sulfanyl moiety. This

  描述了使用甲醇镁作为固体碱催化剂的硝基芳烃（在邻位或对位具有吸电子基团）与烷基硫醇或芳基硫醇之间的亲核芳族取代反应 (SN Ar)。该方法通过用硫烷基部分对硝基进行亲核置换，从芳基硫化物产生一系列有价值的化合物。这种简便的方法是一种合成有用的方法，重要的是在N，N-二甲基甲酰胺中，甲醇镁作为碱有效地促进亲核试剂。亚硝酸根离子的置换发生在导致缺电子环的各种官能团的存在下，例如醛、酮、酯、氰基和硝基。
• Synthesis and electrochemical characterization of CoII, NiII, and CuII complexes with organic N2S2-type ligands derived from 2-thio-substituted benzaldehydes and aromatic amines
  作者：E. K. Beloglazkina、A. V. Shimorsky、A. G. Majouga、A. A. Moiseeva、N. V. Zyk

  DOI：10.1007/s11172-007-0344-1

  日期：2007.11

  are reaction products of 2-thio-substituted benzaldehydes with aromatic amines (3-aminopyridine or 2-aminothiophenol), were synthesized for the first time. The complexes have the composition L·MX2 or L·2MX2 (X = Cl or ClO4). The electrochemical behavior of the ligands and complexes was studied by cyclic voltammetry and rotating disk electrode voltammetry. Depending on the structure of the complexes

  首次合成了具有四齿 N2S2 型配体 (L) 的过渡金属配合物 (NiII、CoII 和 CuII)，它们是 2-硫代苯甲醛与芳香胺（3-氨基吡啶或 2-氨基苯硫酚）的反应产物。时间。复合物的组成为 L·MX2 或 L·2MX2（X = Cl 或 ClO4）。通过循环伏安法和旋转圆盘电极伏安法研究了配体和配合物的电化学行为。根据配合物的结构，后者中的金属原子最初在一个或两个电子过程中被还原。
• Synthesis and physicochemical study of NiII complexes with tetradentate acyclic and macrocyclic N2S2 ligands as thiosalen analogs
  作者：K. P. Butin、A. A. Moiseeva、E. K. Beloglazkina、Yu. B. Chudinov、A. A. Chizhevskii、A. V. Mironov、B. N. Tarasevich、A. V. Lalov、N. V. Zyk

  DOI：10.1007/s11172-005-0234-3

  日期：2005.1

  icylidene)iminate and macrocyclic dithiadiazadibenzocycloalkadiene complexes of nickel(II) were synthesized and their electrochemical and spectroscopic properties were studied. Dithiadiazadibenzocycloalkadiene complexes containing two DMSO molecules coordinated to Ni2+ and two outer-sphere ClO4− anions were synthesized by the reaction of the corresponding macrocyclic ligands with Ni(ClO4)2·6H2O. The

  合成了镍(II)的N,N'-聚亚甲基双(硫代水杨基)亚胺盐和大环二硫代二氮杂二苯并环二烯配合物，并研究了它们的电化学和光谱特性。通过相应的大环配体与 Ni(ClO4)2·6H2O 的反应，合成了含有与 Ni2+ 配位的两个 DMSO 分子和两个外球 − 阴离子的二噻二氮杂二苯并环二烯配合物。3,6-dithia-10,14-diazadibenzo[a,g]cyclopentadeca-9,14-dienylnickel(II)[双(二甲基亚砜)双高氯酸盐]的结构是通过X射线衍射建立的。UV-Vis 光谱数据与二亚氨基二（硫化物）配合物的八面体结构、硫唑嘌呤配合物的方形平面结构和其他二亚氨基二硫醇配合物的扭曲四面体结构一致。S-叔丁基硫代水杨醛与水合肼反应得到二(邻-叔丁基硫代苯扎)嗪。后者与无水 NiCl2 的反应以 15% 的产率生成具有最简单分子式 Ni(C16H12N2S2)
• Baldwin, Darren; Duckworth, Paul A.; Erickson, Gary R., Australian Journal of Chemistry, 1987, vol. 40, # 11, p. 1861 - 1872
  作者：Baldwin, Darren、Duckworth, Paul A.、Erickson, Gary R.、Lindoy, Leonard F.、McPartlin, Mary、et al.

  DOI：——

  日期：——
• Copper N2S2 Schiff base macrocycles: The effect of structure on redox potential
  作者：Michelle K. Taylor、Katherine D. Trotter、John Reglinski、Leonard E.A. Berlouis、Alan R. Kennedy、Corinne M. Spickett、Rebecca J. Sowden

  DOI：10.1016/j.ica.2008.02.021

  日期：2008.6

  A series of bis-salicylidene based N(2)S(2) copper macrocycles were prepared, structurally characterised and subjected to electrochemical analysis. The aim was to investigate the effects of length of polymethylene chains between either the imine donors or the sulfur donors on redox state and potential of the metal. The complexes structurally characterised had either distorted square planar or tetrahedral geometries depending on their oxidation state (Cu(2+) or Cu(+), respectively), and the N-(CH(2))(n)-N bridge was found to be most critical moiety in determining the redox potential and oxidation state of the copper macrocycles, with relatively little change in these properties caused by lengthening the S-(CH(2))(n)-S bridge from two to three carbons. In fact, a weakness was observed in the complexes at the sulfur donor, as further lengthening of the S-(CH(2))(n)-S methylene bridge to four carbons caused fission of the carbon-sulfur bond to give dimeric rings and supramolecular assemblies. Cu(+) complexes could be oxidised to Cu(2+) by tert-butylhydroperoxide, with a corresponding change in the spectrophotometric properties, and likewise Cu(2+) complexes could be reduced to Cu(+) by treatment with beta-mercaptoethylamine. However, repeated redox cycles appeared to compromise the stability of the macrocycles, most probably by a competing oxidation of the ligand. Thus the copper N(2)S(2) macrocycles show potential as redox sensors, but further development is required to improve their performance in a biochemical environment. (c) 2008 Elsevier B. V. All rights reserved.