methylenebis(4,4'-methyl-6,6'-salicylaldehyde) | 502545-54-2

• 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: methylenebis(4,4'-methyl-6,6'-salicylaldehyde)
• 英文别名: 2,2′-methylenebis(4-methyl-6-formylphenol)；3,3'-methylenebis(2-hydroxy-5-methylbenzaldehyde)；2,2'-methylene bis(4-methyl-6-formylphenol)；3-[(3-Formyl-2-hydroxy-5-methylphenyl)methyl]-2-hydroxy-5-methylbenzaldehyde
• CAS: 502545-54-2
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: JHWOOITWSWAFPG-UHFFFAOYSA-N

物化性质

• 沸点：
  424.4±45.0 °C(Predicted)
• 密度：
  1.283±0.06 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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  methylenebis(4,4'-methyl-6,6'-salicylaldehyde) 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以92%的产率得到2-(3-羟甲基-2-羟基-5-甲基苄基)-6-羟甲基-4-甲基苯酚
  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-(3-羟甲基-2-羟基-5-甲基苄基)-6-羟甲基-4-甲基苯酚 在 乌洛托品 、 三氟乙酸 、 水 作用下， 反应 7.0h， 以71.7%的产率得到methylenebis(4,4'-methyl-6,6'-salicylaldehyde)
  参考文献：
  名称：

  METHOD FOR PRODUCING NEW POLYNUCLEAR POLY(FORMYLPHENOL)

  摘要：

  在工业环境中，通过在酸的存在下使多核聚氢甲基酚或多核聚烷氧甲基酚与六亚甲基四胺反应，然后水解所得的反应产物，轻松高纯度地制备目标物质或由通式（2）表示的多核聚甲酰苯酚。

  公开号：

  US20090182175A1

文献信息

• Dinuclear aluminum complexes supported by amino- or imino-phenolate ligands: synthesis, structures, and ring-opening polymerization catalysis of rac-lactide
  作者：Xiao-Feng Yu、Zhong-Xia Wang

  DOI：10.1039/c2dt32520a

  日期：——

  Two series of ligand precursors [2-OH-3-(CH2NR2)-5-MeC6H2]2CH2 (1: NR2 = NMe2; 2: NR2 = N(CH2)4; 3: NR2 = N(CH2)5; 4: NR2 = N(Me)Ph) and [2-OH-3-(CHNR)-5-MeC6H2]2CH2 (10: R = 2,6-Pri2C6H3; 11: R = p-MeC6H4; 12: R = p-ClC6H4; 13: R = p-MeOC6H4; 14: R = But) were prepared. These compounds reacted with AlMe3 to afford corresponding dinuclear aluminum complexes [AlMe22-O-3-(CH2NR2)-5-MeC6H2}]2CH2 (6: NR2 = NMe2; 7: NR2 = N(CH2)4; 8: NR2 = N(CH2)5; 9: NR2 = N(Me)Ph) and [AlMe22-O-3-(CHNR)-5-MeC6H2}]2CH2 (15: R = 2,6-Pri2C6H3; 16: R = p-MeC6H4; 17: R = p-ClC6H4; 18: R = p-MeOC6H4; 19: R = But). All the compounds were characterized by 1H and 13C NMR spectroscopy and elemental analyses. Complexes 6 and 16 were additionally characterized by single crystal X-ray diffraction techniques. Catalysis of the aluminum complexes towards the ring-opening polymerization of rac-lactide was evaluated in the presence of benzyl alcohol. All the polymerization reactions proceed in a controlled manner.

  两个系列的配体前体[2-OH-3-( NR2)-5-MeC6H2]2 （1：NR2 = NMe2；2：NR2 = N(CH2)4；3：NR2 = N( )5；4：NR2=N(Me)Ph）和[2-OH-3-(CHNR)-5-MeC6H2]2 （10：R=2,6-Pri2C6H3；11：R=p-MeC6H4；12：R=p-ClC6H4；13：R=p-MeOC6H4；14：R=But）。这些化合物与 AlMe3 反应生成相应的双核铝配合物 [AlMe22-O-3-( NR2)-5-MeC6H2}]2 （6：NR2 = NMe2；7：NR2 = N( )4；8：9: NR2 = N(Me)Ph) 和 [AlMe22-O-3-(CHNR)-5-MeC6H2}]2 (15: R = 2,6-Pri2C6H3; 16: R = p-MeC6H4; 17: R = p-ClC6H4; 18: R = p-MeOC6H4; 19: R = But)。所有化合物都通过 1H 和 13C NMR 光谱及元素分析进行了表征。此外，还利用单晶 X 射线衍射技术对络合物 6 和 16 进行了表征。在苯甲醇存在下，评估了铝络合物对 rac-内酰胺开环聚合反应的催化作用。所有聚合反应都以受控方式进行。
• Calixarene and hemicarcerand-like compounds obtained by self-assembly of 3-aminophenylboronic acid and salicylaldehyde derivatives
  作者：Victor Barba、Paola Ramos、Danae Jiménez、Abraham Rivera、Ariel Meneses

  DOI：10.1016/j.ica.2013.02.033

  日期：2013.5

  One-pot synthesis of calixarene and hemicarcerand like compounds can be modulated by use of mono- or bis-salicylaldehyde derivatives respectively, reacting with 3-aminophenylboronic acid. Thus, the first part of this work is focused on the synthesis of calix-like compounds derived from salicylaldehyde units including different substituents on the aromatic moiety. Seven different calix structures are described and their structural analysis has been carried out by spectroscopic techniques. The second part corresponds to the description of bis-salicylaldehyde derivatives, synthesis and reactivity towards the 3-aminophenylboronic acid leading to the formation of hemicarcerand-like compounds. Aliphatic and aromatic chains were inserted as linkers between the two salicylaldehyde units in order to evaluate the influence on the formation of the hemicarcerands compounds. Both, calixarene and hemicarcerand compounds resulted from condensation reactions, wherein the formation of N-B coordination bonds plays a significant role on the macrocyclization process. (C) 2013 Elsevier B.V. All rights reserved.
• Syntheses of large-membered macrocycles having multiple hydrogen bonding moieties
  作者：Hisashi Shimakoshi、Takayuki Kai、Isao Aritome、Yoshio Hisaeda

  DOI：10.1016/s0040-4039(02)02022-1

  日期：2002.11

  New macrocyclic Compounds have been synthesized by Schiff-base condensation reaction with methylenebis(4.4'-methyl-6,6'-salicylaldehyde) and 1,2-bis(2-aminoethoxy)ethane based on a high dilution method. [2+2], [3+3], and [4+4]-Cyclocondenced products were effectively isolated and characterized by H-1 NMR and HR mass (FAB) spectroscopies as well as X-ray analyses. Reduction or the macrocycles with NaBH4 afforded the corresponding multi-amino, miulti-phenolic macrocyclic Compounds. The reduced molecules have low energy barriers for conformation change, which are estimated by variable-temperature (VT) H-1 NMR study. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US7750190B2
  申请人：——

  公开号：US7750190B2

  公开（公告）日：2010-07-06
• USRE43067E1
  申请人：——

  公开号：USRE43067E1

  公开（公告）日：2012-01-03