Salicylaldehyde

• 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: Salicylaldehyde
• 英文别名: (3-tert-butyl-5-formyl-4-hydroxybenzyl)triphenylphosphonium chloride；(3-Tert-butyl-5-formyl-4-hydroxyphenyl)methyl-triphenylphosphanium;chloride；(3-tert-butyl-5-formyl-4-hydroxyphenyl)methyl-triphenylphosphanium;chloride
• 化学式: C₃₀H₃₀O₂P*Cl
• 分子量: 488.994
• InChiKey: KETMCIQPQZYFDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Salicylaldehyde 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (R,R)-N,N'-bis(3-tert-butyl-5-vinylsalicylidene)-1,2-cyclohexanediamine
  参考文献：
  名称：

  通过新的轴向配位连接剂将手性锰（III）赛伦催化剂固定在MCM-41上以及层状沸石ITQ-2和ITQ-6上

  摘要：

  我们报告说，锚定在传统载体（例如MCM-41（孔径为38Å）和分层沸石材料ITQ-2和ITQ-6）上的三种不同的手性Mn（III）萨伦配合物的催化行为和对映选择性在很大程度上取决于是否配合物通过手性赤道四齿萨利恩配体或通过顶端配体连接到表面。至于无载体配合物的情况，该实验观察已经考虑到催化剂中间体对接近的烯烃的构象偏好的强烈变化，以及配合物中不利的结构变化。另外，控制表面的疏水性允许优化获得手性环氧化物的选择性。

  DOI：

  10.1016/j.jcat.2004.08.021
• 作为产物：
  描述：

  3-叔丁基-2-羟基苯甲醛 在 盐酸 作用下， 以 苯 为溶剂， 反应 75.0h， 生成 Salicylaldehyde
  参考文献：
  名称：

  Synthesis and characterization of bulky salen-type complexes of Co, Cu, Fe, Mn and Ni with amphiphilic solubility properties

  摘要：

  几种新型大体积萨伦型希夫碱配体及其与第一排过渡金属Co、Cu、Fe、Mn和Ni的配合物已被合成和表征。该配体在芳环中含有叔丁基和甲基（三苯基氯化鏻）取代基，提供灵活的溶​​解性能。确定了一些配合物的晶体结构。

  DOI：

  10.1039/b008167l

文献信息

• Quaternary onium modified SalenCoXY catalysts for alternating copolymerization of CO2 and propylene oxide: A kinetic study
  作者：Xiying Fu、Huanwang Jing

  DOI：10.1016/j.jcat.2015.05.030

  日期：2015.9

  Quaternary onium modulated SalenCoXY (X = Cl, Br, NO3; Y = phenoxy, benzene-1,4-bisoxy, benzene-1,3,5-trisoxy) catalysts incorporating the N,N′-bis(salicylidene)ethylene diaminato(Salen) ligand and quaternary onium units were designed, synthesized and applied to the copolymerization of CO2 and propylene oxide. The impact factors of the axial anion X, the counter anion Y and the property of quaternary

  季铵盐调制的SalenCoXY（X = Cl，Br，NO 3 ; Y =苯氧基，苯-1,4-双氧基，苯-1,3,5-三氧基）催化剂，结合了N，N'-双（水杨基）乙二胺设计，合成（Salen）配体和季鎓单元，并将其应用于CO 2和环氧丙烷的共聚。轴向阴离子X，抗衡阴离子Y和季鎓基团的性质的影响因素明显影响PPC的选择性和聚合度。详细的动力学研究以及环加成和共聚的机理已得到记录和讨论。限制性地提出了用于聚合的第二级催化剂。
• Immobilization of cationic Al(III) salen in the interlayers of montmorillonite clay for the synthesis of cyclic carbonate
  作者：Shailesh Verma、Rukhsana I. Kureshy、Tamal Roy、Manish Kumar、Anjan Das、Noor-ul H. Khan、Sayed H.R. Abdi、Hari C. Bajaj

  DOI：10.1016/j.catcom.2014.12.013

  日期：2015.2

  Cationic Al(III) salen complex immobilized in the interlayer of montmorillonite clay 1-Mont (0.25 mol%) was used as an effective immobilized catalyst for the synthesis of cyclic carbonates from various epoxides at atmospheric pressure with excellent conversion (99%), selectivity (99%) and high degree of catalyst recyclability.

  固定在蒙脱石粘土1-Mont（0.25 mol％）中间层中的阳离子Al（III）salen络合物用作有效的固定化催化剂，可在大气压下由各种环氧化物合成环状碳酸酯，并具有出色的转化率（99％），选择性（99％）和高度的催化剂可回收性。
• Heterogeneous chiral Mn(III) salen catalysts for the epoxidation of unfunctionalized olefins immobilized on mesoporous materials with different pore sizes
  作者：Kai Yu、Zhicheng Gu、Runan Ji、Lan-Lan Lou、Shuangxi Liu

  DOI：10.1016/j.tet.2008.10.051

  日期：2009.1

  Two chiral Mn(III) salen complexes were immobilized onto a series of mesoporous MCM-41 and MCM-48 materials with different pore sizes and the as-synthesized catalysts were active and enantioselective for the asymmetric epoxidation of styrene and indene. The results of XRD, FTIR, DR UV–vis, and N2 sorption showed that the chiral Mn(III) salen complexes were anchored in the channels of mesoporous materials

  将两种手性Mn（III）salen配合物固定在一系列具有不同孔径的介孔MCM-41和MCM-48材料上，合成的催化剂对苯乙烯和茚的不对称环氧化具有活性和对映选择性。XRD，FTIR，DR UV-vis和N 2的结果吸附表明手性Mn（III）salen配合物锚定在介孔材料的通道中。研究了有机硅用量对催化性能的影响，确定了用于制备多相催化剂的最佳有机硅用量。此外，讨论了孔径微调对非均相催化剂性能的影响。通常，载体的较大孔径可导致更高的转化率，并且与底物相容的孔径可能是改善对映体过量（ee）值的原因。
• Heterogeneous asymmetric epoxidation of unfunctionalized olefins catalyzed by polymer-bound (salen)manganese complexes
  作者：Filippo Minutolo、Dario Pini、Antonella Petri、Piero Salvadori

  DOI：10.1016/0957-4166(96)00284-4

  日期：1996.8

  The synthesis of three different polymer-bound chiral Mn-salen complexes (Poly-1, -2a, -2b) is reported, along with their application as recyclable catalysts in heterogeneous asymmetric epoxidation with mCPBA/NMO of several unfunctionalized olefins. The introduction of a spacing group between the polymeric chain and the metal centre (Poly-2a and -2b) considerably increased the enantioselectivity of the process. Copyright (C) 1996 Elsevier Science Ltd
• Asymmetric alkene epoxidation by Mn(III)salen catalyst in ionic liquids
  作者：Jorge Teixeira、Ana Rosa Silva、Luís C. Branco、Carlos A.M. Afonso、Cristina Freire

  DOI：10.1016/j.ica.2010.06.018

  日期：2010.10

  The enantioselective epoxidation of 6-cyano-2,2-dimethylchromene (Chrom) catalysed by the Jacobsen catalyst, using sodium hypochlorite (NaOCl) as oxygen source, at room temperature, was performed in a series of 1,3-dialkylimidazolium and tetra-alkyl-dimethylguanidium based ionic liquids. All the room temperature ionic liquids (RTILs) could be used as reaction media for the enantioselective epoxidation of the alkene giving, generally, moderate to good epoxide yields and enantiomeric excesses (ee%).For the series of ionic liquids derived from the 1,3-dialkylimidazolium cation, it was observed some relationship between the RTILs physical properties and the catalytic reaction parameters, exemplified by linear correlations between (i) the ee% and the alpha Kamlet-Taft parameter (hydrogen bond acidity of the solvent) for CH2Cl2 and [C(4)m(n)im][BF4] ionic liquids (n = 1 or 2), and (ii) the ee% and the beta Kamlet-Taft parameter (hydrogen bond basicity of the solvent) for CH2Cl2 and [C(4)mim][X] ionic liquids (X = PF6, NTf2 or BF4).All the RTILs could be reused in further catalytic cycles, with the exception of [C(8)mim][PF6]. The reutilisation of the Jacobsen catalyst for four times generally led to a decrease in the epoxide yield and to a slight decrease in the enantioselectivity. The recycling of the catalyst could be improved by imparting an ionic character to the complex through abstraction of the axially coordinated chloride anion (Cat 2). Other oxygen sources, such as iodosylbenzene, hydrogen peroxide and urea-hydrogen peroxide adduct, were also tested coupled with Jacobsen catalyst, but the best results were achieved with NaOCl. (C) 2010 Elsevier B.V. All rights reserved.