1,4-phenylenebis(methylene) bis(4-formylbenzoate) | 454661-52-0

• 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: 1,4-phenylenebis(methylene) bis(4-formylbenzoate)
• 英文别名: [4-[(4-Formylbenzoyl)oxymethyl]phenyl]methyl 4-formylbenzoate
• CAS: 454661-52-0
• 化学式: C₂₄H₁₈O₆
• 分子量: 402.403
• InChiKey: PDWLLVLKXFUVFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-phenylenebis(methylene) bis(4-formylbenzoate) 、 邻苯二胺 在 sodium hydrogensulfite 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以66%的产率得到1,4-phenylenebis(methylene)bis(4-(1H-benzo[d]imidazol-2-yl)benzoate)
  参考文献：
  名称：

  新型双和聚苯并咪唑类以及双和聚苯并噻唑类化合物的合成

  摘要：

  尝试使用不同的方案合成双和聚苯并咪唑以及双和聚苯并噻唑。通过在NaHSO 3存在下，在乙醇中回流使适当的双醛或多醛分别与邻苯二胺或2-氨基硫酚反应，可获得最佳结果。评估了合成化合物对人乳腺癌细胞系（MCF-7），肝癌细胞系（HepG-2）和上皮结直肠腺癌细胞（CaCO-2）的抗癌活性。已发现Hexakis（苯并噻唑）对HepG-2和MCF-7细胞系的活性最高，IC 50值分别为21.16和13.25μM。

  DOI：

  10.1002/jhet.3947
• 作为产物：
  描述：

  1,4-二(溴甲基)苯 、 对醛基苯甲酸 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.42h， 以76%的产率得到1,4-phenylenebis(methylene) bis(4-formylbenzoate)
  参考文献：
  名称：

  Polyaldol Synthesis by Direct Organocatalyzed Crossed Polymerization of Bis(ketones) and Bis(aldehydes)

  摘要：

  Synthesis of polyaldols consisting of beta-keto alcohol monomer units is described. These polymers were obtained by direct step-growth polymerization of purposely designed bifunctional enolizable bis(ketone) monomers playing the role of nucleophilic donors, and activated nonenolizable bis(aldehyde)s serving as electrophilic acceptors. Monofunctional ketone and aldehyde homologues were first synthesized as models to establish the aldol reaction conditions using reaction partners at stoichiometry. A bifunctional organocatalytic system consisting of pyrrolidine in conjunction with acetic acid allowed performing polyaldolizations of stoichiometric amounts of the bis(aldehyde) and the bis(ketone) in solution in THF, DMSO, or DMF, at room temperature. However, polar solvents and/or prolonged reaction time induced further aldol reactions between aldol units of polymer chains, as indicated by the relatively broad molecular weight distribution of related polyaldols observed by size exclusion chromatography. Analysis by NMR spectroscopy confirmed the formation of beta-keto alcohol units, but also evidenced that the latter were also partly dehydrated into conjugated ketones via a crotonization reaction (from 20 to 33% depending on the structure of the initial monomers).

  DOI：

  10.1021/ma402108y

文献信息

• Hantzsch one-pot multicomponent synthesis of a novel series of <i>bis</i>(9,10-diarylhexahydroacridine-1,8-diones)
  作者：Amr M. Abdelmoniem、Hadeel F. Hammad、Ahmed F. Darweesh、Mahfouz A. Abdelaziz、Ismail A. Abdelhamid、Ahmed H. M. Elwahy

  DOI：10.1080/00397911.2021.1956541

  日期：2021.9.2

  to aliphatic, aromatic, or heteroaromatic spacers via ether or ester linkages. The target products were obtained in good to excellent yields via a multi-component reaction of the appropriate aromatic amine, 5,5-dimethyl-1,3-cyclohexanedione, and the corresponding bis-aldehydes. The reactions were also proceeded to give the target products in good yields via a multi-component reaction of the appropriate

  摘要 已经开发了用于合成新型双(9,10-二芳基-六氢吖啶-1,8-二酮)系列的有效程序，其中两个吖啶部分通过醚或酯键连接到脂肪族、芳香族或杂芳香族间隔基。通过适当的芳香胺、5,5-二甲基-1,3-环己二酮和相应的双醛的多组分反应，以良好至极好的收率获得目标产物。将反应物也进行，得到高产率的目标产物通过合适的环状烯胺的多组分反应，和相应的二-醛类似的条件下。双适当的六氢吖啶-1,8-二酮与相应的二卤化合物在碱性介质中的烷基化也被证明是合成目标产物的有效策略。芳香胺、双醛和巴比妥酸或 1,3-二甲基巴比妥酸而不是 5,5-二甲基-1,3-环己二酮的多组分反应以良好的收率提供了相应的 Knoevenagel 缩合加合物，但不幸的是，预期的双-四氢嘧啶并[4,5- b ]喹啉无法分离。
• 3‐Amino‐5‐cyanomethylpyrazole‐4‐carbonitrile: Versatile Reagent for Novel Bis(pyrazolo[1,5‐<i>a</i>]pyridine) Derivatives<i>via</i>a Multicomponent Reaction
  作者：Amr M. Abdelmoniem、Said A. S. Ghozlan、Doaa M. Abdelmoniem、Ahmed H. M. Elwahy、Ismail A. Abdelhamid

  DOI：10.1002/jhet.3346

  日期：2018.12

  An efficient synthesis of novel bis(pyrazolo[1,5‐a]pyridine) derivatives through Michael addition reaction of 3‐amino‐5‐cyanomethylpyrazole‐4‐carbonitrile with bis‐arylidenemalononitrile is reported. All new compounds are characterized by different spectral tools.

  据报道，通过3-氨基-5-氰基甲基吡唑-4-腈与双芳基丙二腈的迈克尔加成反应可以有效合成新型双（吡唑并[1,5- a ]吡啶）衍生物。所有新化合物都具有不同的光谱工具。
• Polyaldol Synthesis by Direct Organocatalyzed Crossed Polymerization of Bis(ketones) and Bis(aldehydes)
  作者：Na Liu、Anthony Martin、Frédéric Robert、Jean-Marc Vincent、Yannick Landais、Joan Vignolle、Henri Cramail、Daniel Taton

  DOI：10.1021/ma402108y

  日期：2014.1.28

  Synthesis of polyaldols consisting of beta-keto alcohol monomer units is described. These polymers were obtained by direct step-growth polymerization of purposely designed bifunctional enolizable bis(ketone) monomers playing the role of nucleophilic donors, and activated nonenolizable bis(aldehyde)s serving as electrophilic acceptors. Monofunctional ketone and aldehyde homologues were first synthesized as models to establish the aldol reaction conditions using reaction partners at stoichiometry. A bifunctional organocatalytic system consisting of pyrrolidine in conjunction with acetic acid allowed performing polyaldolizations of stoichiometric amounts of the bis(aldehyde) and the bis(ketone) in solution in THF, DMSO, or DMF, at room temperature. However, polar solvents and/or prolonged reaction time induced further aldol reactions between aldol units of polymer chains, as indicated by the relatively broad molecular weight distribution of related polyaldols observed by size exclusion chromatography. Analysis by NMR spectroscopy confirmed the formation of beta-keto alcohol units, but also evidenced that the latter were also partly dehydrated into conjugated ketones via a crotonization reaction (from 20 to 33% depending on the structure of the initial monomers).
• Synthesis of novel bis‐ and poly(benzimidazoles) as well as bis‐ and poly(benzothiazoles) as anticancer agents
  作者：Ali M. S. Hebishy、Mohamed S. Abdelfattah、Abdullah Elmorsy、Ahmed H. M. Elwahy

  DOI：10.1002/jhet.3947

  日期：2020.5

  A synthesis of bis‐ and poly(benzimidazoles) as well as bis‐ and poly(benzothiazoles) was attempted using different protocols. The best results were obtained by employing the reaction of the appropriate bis‐ or poly(aldehydes) with o‐phenylenediamine or 2‐aminothiophenol, respectively, in ethanol at reflux in the presence of NaHSO3. The anticancer activities of the synthesized compounds were evaluated

  尝试使用不同的方案合成双和聚苯并咪唑以及双和聚苯并噻唑。通过在NaHSO 3存在下，在乙醇中回流使适当的双醛或多醛分别与邻苯二胺或2-氨基硫酚反应，可获得最佳结果。评估了合成化合物对人乳腺癌细胞系（MCF-7），肝癌细胞系（HepG-2）和上皮结直肠腺癌细胞（CaCO-2）的抗癌活性。已发现Hexakis（苯并噻唑）对HepG-2和MCF-7细胞系的活性最高，IC 50值分别为21.16和13.25μM。