2,2'-dihydroxy-5,5'-di-tert-butyl-3,3'-methanediyl dibenzaldehyde | 475197-29-6

• 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'-dihydroxy-5,5'-di-tert-butyl-3,3'-methanediyl dibenzaldehyde
• 英文别名: 3,3'-Methylenebis(5-(tert-butyl)-2-hydroxybenzaldehyde)；5-tert-butyl-3-[(5-tert-butyl-3-formyl-2-hydroxyphenyl)methyl]-2-hydroxybenzaldehyde
• CAS: 475197-29-6
• 化学式: C₂₃H₂₈O₄
• 分子量: 368.473
• InChiKey: VLDUFMNESGFZGG-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  460.8±45.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2'-dihydroxy-5,5'-di-tert-butyl-3,3'-methanediyl dibenzaldehyde 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 76.0h， 生成 2-<3-<3-(5-tert-Butylsalicyl)-5-tert-butylsalicyl>-5-tert-butylsalicyl>-4-tert-butylphenol
  参考文献：
  名称：

  单官能杯[5]芳烃的合成

  摘要：

  摘要 按照片段缩合方案，制备了七个带有额外的甲基或叔丁基的无OH和O-全甲基化的杯芳烃[5]芳烃。事实证明，此策略优于以前的方法。带有游离OH基的杯[5]芳烃均采用在下部边缘通过氢键接缝稳定的视锥构象。也可以实现缩合后修饰，即酚羟基的甲基化或官能团的相互转化。还发现大的叔丁基可稳定O的圆锥构象-甲基化的化合物。这些化合物提供了多功能的官能团，这些官能团使这些凹形分子成为合成更复杂的分子结构的有趣构建基块。 按照片段缩合方案，制备了七个带有额外的甲基或叔丁基的无OH和O-全甲基化的杯芳烃[5]芳烃。事实证明，此策略优于以前的方法。带有游离OH基的杯[5]芳烃均采用在下部边缘通过氢键接缝稳定的视锥构象。也可以实现缩合后修饰，即酚羟基的甲基化或官能团的相互转化。还发现大的叔丁基可稳定O的圆锥构象-甲基化的化合物。这些化合物提供了多功能的官能团，这些官能团使这些凹形分子成为合成更复杂的分子结构的有趣构建基块。

  DOI：

  10.1055/s-0036-1589127
• 作为产物：
  描述：

  2,2'-bis(allyloxy)-5,5'-di-tert-butyl-3,3'-methanediyldibenzenemathanol 在 palladium on activated charcoal manganese(IV) oxide 作用下， 生成 2,2'-dihydroxy-5,5'-di-tert-butyl-3,3'-methanediyl dibenzaldehyde
  参考文献：
  名称：

  拟杯芳烃大环的双核配合物：分子内氢键的结构后果

  摘要：

  一系列拟杯芳烃的双核配合物 大循环含有两个2,2'-亚甲基二酚基团的H 6 L已被合成并进行了结构表征。使用二价金属离子，形成含有常见双曲线抛物面（鞍形）M 2（H 4 L）2+核的配合物。该结构由亚甲基二酚单元的金属离子促进的单去质子化作用产生的两个强烈的O–H–O相互作用控制。金属离子位于裂缝中，中性或阴离子客体可与之结合。使用三价金属离子会导致苯酚基团完全去质子化并失去鞍形构象。

  DOI：

  10.1039/b413639j

文献信息

• Binuclear Cu(II) chiral complexes: synthesis, characterization and application in enantioselective nitroaldol (Henry) reaction
  作者：E. Chinnaraja、R. Arunachalam、Manoj K. Choudhary、R. I. Kureshy、P. S. Subramanian

  DOI：10.1002/aoc.3404

  日期：2016.2

  l)‐2‐hydroxybenzaldehyde) and characterized. The chirality transfer and chiral inversion from ligand to copper(II) metal centre were studied using circular dichroism spectroscopy. The enantiopure binuclear copper(II) complexes (ΔΔ and ΛΛ) were used as catalysts for asymmetric nitroaldol reaction to generate β‐nitroalcohol with 88% yield and 67% enantioselectivity. Copyright © 2015 John Wiley & Sons

  对映纯大环配体由（1 R，2 R）-（+）-和（1 S，2 S）-（-）-二苯基乙二胺与3,3'-亚甲基双（5-（叔-丁基）-2-羟基苯甲醛）并进行了表征。利用圆二色谱法研究了从配体到铜（II）金属中心的手性转移和手性反转。将对映纯双核铜（II）配合物（ΔΔ和ΛΛ）用作不对称硝基羟醛反应的催化剂，以88％的收率和67％的对映选择性生成β-硝基醇。版权所有©2015 John Wiley＆Sons，Ltd.
• Synthesis, Characterization and X-Ray Crystal Structure of Dizinc(II) Complex of Pseudo Calixarene Macrocycle Based on 2,2-Methylene-bis[(6-formyl)-4-tert-butylphenol] and 1,3-Diamino-2-propanol
  作者：Imdad Hussain、Rubina Gillani、Vickie McKee、Muhammet Kose、Zulfiqar Ali、Habib Hussain

  DOI：10.14233/ajchem.2015.18658

  日期：——

  [(2+2)Zn2·CH3COO] complex was prepared by refluxing 2,2-methylene-bis[(6-formyl)-4-tert-butylphenol] (H2mftbp) and 1,3-diamino-2-propanol in a round-bottomed flask containing Ca(ClO4)2 in ethanol in the presence of a base. Sample was taken from the refluxing solution and submitted for MS. ESI-MS showed the peak to confirm the formation of calcium complex [(2+2)Ca] but when Zn(CH3COO)2·2H2O was added and refluxed for further 6 h. Zinc replaced calcium metal and a new complex of Zn was formed as [Zn2(2+2)] complex. A yellow powder was filtered after cooling at room temperature. The powder was crystallized by vapour diffusion method. The complex crystallizes in the monoclinic crystal system with space group P2(1)/n. Unit cell parameters are; a = 13.6595(7) Å, b = 18.5216(9) Å, c = 25.0723(12) Å, a = 90°, b = 95.7020(10)°, g = 90°, Z = 8 and V= 6311.8(5) Å3. The complex was characterized by using single crystal X-ray spectroscopy, IR-spectroscopy and ESI-mass spectrophotometery.

  在有碱存在的情况下，将 2,2-亚甲基-双[(6-醛基)-4-叔丁基苯酚]（H2mftbp）和 1,3-二氨基-2-丙醇在含有 Ca(ClO4)2 的乙醇的圆底烧瓶中回流，制备了[(2+2)Zn2-CH3COO]络合物。从回流溶液中提取样品并进行质谱分析。ESI-MS 显示的峰值证实了钙络合物 [(2+2)Ca] 的形成，但当加入 Zn(CH3COO)2-2H2O 并继续回流 6 小时后，锌取代了钙金属，形成了新的锌络合物，即[Zn2(2+2)]络合物。室温冷却后，过滤得到黄色粉末。粉末通过蒸汽扩散法结晶。该复合物在单斜晶系中结晶，空间群为 P2(1)/n。单胞参数为：a = 13.6595(7)埃，b = 18.5216(9)埃，c = 25.0723(12)埃，a = 90°，b = 95.7020(10)°，g = 90°，Z = 8 和 V= 6311.8(5)埃3。利用单晶 X 射线光谱、红外光谱和 ESI-质谱光度计对该复合物进行了表征。
• New macrocyclic ligands having discrete metal binding sites
  作者：Hisashi Shimakoshi、Hiroki Takemoto、Isao Aritome、Yoshio Hisaeda

  DOI：10.1016/s0040-4039(02)00923-1

  日期：2002.7

  New macrocyclic dinucleating ligands have been easily synthesized by Schiff-base condensation reaction with the appropriate aldehyde and amine using the boric ion template method. The ligands have two N2O2 metal-binding sites which are doubly linked to each other with methylene spacers. The ligands chelate with Co2+, Cu2+ and Ni2+ to form dimetallic compounds in high yields.

  使用硼离子模板法，通过与适当的醛和胺进行席夫碱缩合反应，可以轻松合成新的大环二核配体。所述配体具有两个N 2 O 2金属结合位点，所述两个N 2 O 2金属结合位点通过亚甲基间隔基彼此双重连接。所述配体与Co 2 +，Cu 2+和Ni 2+螯合以高产率形成双金属化合物。
• Synthetic approaches to mixed ligand chelators on tert-butylphenol–formaldehyde oligomer (PFO) platforms
  作者：Jennifer A. Young、Sukhen Karmakar、Hollie K. Jacobs、Aravamudan S. Gopalan

  DOI：10.1016/j.tet.2012.09.032

  日期：2012.12

  Synthetic approaches to mixed ligand chelators on readily available tert-butylphenol-formaldehyde oligomer, PFO, scaffolds were examined. In a promising approach, tris and tetraphenol oligomers were selectively mono or di protected using tert-butyldiphenyl silyl chloride. The utility of these protected intermediates to prepare representative mixed PFO chelators, carrying ligands such as hydroxamic acid, 3,2-hydroxypyridinones, and others was then demonstrated. The introduction of the ligand tethers onto the phenolic scaffold can be done sequentially under relatively mild conditions that tolerate the presence of other sensitive ligand groups. The differential reactivity of the disilyl derivative 20b, allowed stepwise introduction of two different ligands on the internal phenolic positions. This enabled the introduction of three different ligand groups of choice onto the tetraphenol platform. (C) 2012 Elsevier Ltd. All rights reserved.
• Iron(III) and manganese(III) complexes of a pseudocalixarene tetraiminotetraphenol macrocyclic ligand: Structure, magnetism and electrochemistry
  作者：Papu Biswas、Pradip Bag、Amit Kumar Dutta、Ulrich Flörke、Kamalaksha Nag

  DOI：10.1016/j.poly.2014.03.011

  日期：2014.6

  The pseudocalixarene tetraiminotetraphenol macrocyclic ligand H4L has been structurally characterized and used to synthesize the complexes [(Fe2L)-L-III(NO3)(2)(H2O)(2)] (1), [(Fe2L)-L-III(Cl)(2)](infinity) (2), [(Fe2L)-L-III(mu-O)}(2)]center dot 2CH(3)CN center dot H2O (3), [(Mn2L)-L-III(Cl)(2)]center dot 3H(2)O (4) and [(Mn2L)-L-III(OAc)(2)]center dot 5H(2)O (5). The crystal structures of 3 and 4 have been determined. Variable-temperature (2-295 K) magnetic susceptibility measurements have been carried out for 3 and the data have been fitted to the spin Hamiltonian H = -2JS(1).S-2 with J = -45 cm(-1). Cyclic voltammetric measurements carried out for 1 in N,N-dimethylformamide have revealed the presence of two reversible redox couples with E-1/2 = -180 and -280 mV, which coalesced into a single couple with E-1/2 = -220 mV with the addition of excess NaNO3. The two manganese(III) complexes undergo quasi-reversible reduction in methanol at the same potential with E-1/2 = -240 mV. (C) 2014 Elsevier Ltd. All rights reserved.