3,4,5-三(苯甲氧基)苯甲醛 | 6137-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3,4,5-三(苯甲氧基)苯甲醛
• 英文名称: 3,4,5-tribenzyloxybenzaldehyde
• 英文别名: 3,4,5-tris(benzyloxy)benzaldehyde；3,4,5-tris(phenylmethoxy)benzaldehyde
• CAS: 6137-86-6
• 化学式: C₂₈H₂₄O₄
• 分子量: 424.496
• InChiKey: ABEPSQZVZNRXCY-UHFFFAOYSA-N

物化性质

• 熔点：
  104-104.5 °C
• 沸点：
  602.7±50.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4,5-三(苯甲氧基)苯甲醛 在 palladium on activated charcoal 吗啉 、 lithium aluminium tetrahydride 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 3-{3,4,5-tris[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl}propan-1-ol
  参考文献：
  名称：

  Synthesis and Retrostructural Analysis of Libraries of AB₃ and Constitutional Isomeric AB₂ Phenylpropyl Ether-Based Supramolecular Dendrimers

  摘要：

  We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 35-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy)phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3,4-bis[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl-1-propyl-, and 3-13,4,5-tris[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyllpropyI ether first-generation clendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from clendritic dipepticles and hollow supramolecular spheres were also discovered from these building blocks. The more flexible and less compact 3-phenylpropyl ether repeat units are stable under acidic conditions, facilitate a simpler synthetic strategy, provide faster dynamics of self-assembly into higher-order supramolecular structures of larger dimensions, exhibit lower transition temperatures than the corresponding benzyl ether homologues, and demonstrate the generality of the self-assembly concept based on amphiphilic dendrons.

  DOI：

  10.1021/ja060062a
• 作为产物：
  描述：

  没食子酸丙酯 在 lithium aluminium tetrahydride 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3,4,5-三(苯甲氧基)苯甲醛
  参考文献：
  名称：

  Synthesis and Retrostructural Analysis of Libraries of AB₃ and Constitutional Isomeric AB₂ Phenylpropyl Ether-Based Supramolecular Dendrimers

  摘要：

  We report the synthesis of methyl esters of 3-(4-hydroxyphenyl)propionic, 3-(3,4-dihydroxyphenyl)propionic, 3-(3,5-dihydroxyphenyl)propionic, and 3-(3,4,5-trihydroxyphenyl)propionic acids and their use in a convergent iterative strategy to prepare up to four generations of three libraries, one of 3,4,5- and two of constitutional isomeric 3,4- and 35-substituted 3-phenylpropyl dendrons. Each library contains 3-[3,4,5-tris(dodecyl-1-oxy)phenyl]propyl-, 3-[3,4-bis(dodecyl-1-oxy)phenyl]propyl-, 3,4-bis[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyl-1-propyl-, and 3-13,4,5-tris[3-(4-dodecyl-1-oxyphenyl)propyl-1-oxy]phenyllpropyI ether first-generation clendrons on their periphery and -CO2CH3, -COOH, and -CH2OH groups at their apex. Regardless of their generation number and their periphery, internal, and apex structures, these dendrons self-assemble into supramolecular dendrimers that self-organize into all periodic and quasi-periodic assemblies encountered previously and in several unencountered with architecturally related benzyl ether-based supramolecular dendrimers. A variety of porous columnar lattices that were previously obtained only from clendritic dipepticles and hollow supramolecular spheres were also discovered from these building blocks. The more flexible and less compact 3-phenylpropyl ether repeat units are stable under acidic conditions, facilitate a simpler synthetic strategy, provide faster dynamics of self-assembly into higher-order supramolecular structures of larger dimensions, exhibit lower transition temperatures than the corresponding benzyl ether homologues, and demonstrate the generality of the self-assembly concept based on amphiphilic dendrons.

  DOI：

  10.1021/ja060062a

文献信息

• Modified Julia-Kocienski Reaction Promoted by Means of m-NPT (Nitro­phenyltetrazole) Sulfone
  作者：Toshiyuki Kan、Yuki Sakai、Kazutada Ikeuchi、Yuji Yamada、Toshiyuki Wakimoto

  DOI：10.1055/s-0029-1219386

  日期：2010.3

  m-Nitrophenyltetrazole sulfone (2) was employed in the Julia-Kocienski reaction. The olefination reaction between 2 and carbonyl compounds proceeded smoothly under Masamune-Roush conditions (DBU and LiCl). These conditions were also applicable to our catechin derivative synthesis. Furthermore, phenolic mesylate was also tolerated in this mild reaction.

  m-硝基苯四唑砜（2）被用于Julia-Kocienski反应。在Masamune-Roush条件下（DBU和LiCl），2与羰基化合物的烯化反应顺利进行。这些条件同样适用于我们的儿茶酚衍生物合成。此外，酚性甲磺酸酯也在这种温和反应中得以耐受。
• Design of an Amide <i>N</i>-Glycoside Derivative of β-Glucogallin: A Stable, Potent, and Specific Inhibitor of Aldose Reductase
  作者：Linfeng Li、Kun-Che Chang、Yaming Zhou、Biehuoy Shieh、Jessica Ponder、Adedoyin D. Abraham、Hadi Ali、Anson Snow、J. Mark Petrash、Daniel V. LaBarbera

  DOI：10.1021/jm401311d

  日期：2014.1.9

  inhibitor of aldose reductase (AKR1B1). New linkages (ether/triazole/amide) were introduced via high yielding, efficient syntheses to replace the labile ester, and an original two-step (90%) preparation of BGG was developed. Inhibition of AKR1B1was assessed in vitro and using transgenic lens organ cultures, which identified the amide linked glucoside (BGA) as a stable, potent, and selective therapeutic

  β-Glucogallin（BGG），所述的主要成分余甘厚朴药用植物，是醛糖还原酶（AKR1B1）的强效的和选择性的抑制剂。通过高产、高效的合成引入了新的键（醚/三唑/酰胺）以替代不稳定的酯，并开发了 BGG 的原始两步 (90%) 制备。在体外和使用转基因晶状体器官培养物评估了对 AKR1B1 的抑制作用，发现酰胺连接的葡萄糖苷 (BGA) 是一种稳定、有效和选择性的治疗糖尿病眼病的先导药物。
• Benzylidene thiazolidinediones and their use as antimycotic agents
  申请人：Oxford GlycoSciences (UK) Ltd

  公开号：US20040006112A1

  公开（公告）日：2004-01-08

  A compound of formula I or a salt thereof wherein, A is O or S, X and Y independently represent O, CH 2 and may be the same or different, Q is (CH 2 ) m —CH(R1)—(CH 2 ) n , R is OR6, NHR8, R1 is hydrogen, or optionally substituted alkyl, R2 and R3 are independently hydrogen, or specific substituents, provided that R2 and R3 are not both H, and R4 and R5 are hydrogen or specific substituents, m is 0-3; n is 0-2; are useful in the treatment of fungal infections.

  公式I的化合物或其盐，其中，A为O或S，X和Y分别代表O、CH2，可以相同也可以不同，Q为(CH2)m—CH(R1)—(CH2)n，R为OR6，NHR8，R1为氢，或者可选择地取代的烷基，R2和R3独立地为氢，或者特定的取代基，但要求R2和R3不同时为H，R4和R5为氢或者特定的取代基，m为0-3；n为0-2；在治疗真菌感染中是有用的。
• Inhibitory Activity of Catechin Metabolites Produced by Intestinal Microbiota on Proliferation of HeLa Cells
  作者：Aya Hara-Terawaki、Akiko Takagaki、Hirotsugu Kobayashi、Fumio Nanjo

  DOI：10.1248/bpb.b17-00127

  日期：——

  Eleven kinds of catechin metabolites produced from (−)-epigallocatechin (EGC) and (−)-epigallocatechin gallate (EGCg) by intestinal microbiota were evaluated for inhibitory activity on the proliferation of HeLa cells, which are human cervical cancer cells. Among the catechin metabolites, 1-(3,4,5-trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol (EGC-M2), 4-hydroxy-5-(3,4,5-trihydroxyphenyl)valeric acid (EGC-M7), and 5-(3,4,5-trihydroxyphenyl)valeric acid (EGC-M9) were found to show inhibitory activity on HeLa cell proliferation as compared with control. The results suggested that three adjacent hydroxyl groups in the phenyl moiety may play an important role in the inhibitory activity. In addition, the inhibitory activity was also examined with four (−)-epicatechin (EC) metabolites possessing two adjacent hydroxyl groups in the phenyl moiety. Only 5-(3,4-dihydroxyphenyl)valeric acid (EC-M9) showed inhibitory activity and therefore valeric acid moiety likely contributes to the inhibitory activity. EGC-M9 showed the strongest inhibitory activity with IC50 of 5.58 µM. Thus, in this study it was found for the first time that several catechin metabolites derived from EGC, EGCg, and EC inhibit the proliferation of cervical cancer cells.

  由肠道微生物群产生的(-)-表没食子儿茶素(EGC)和(-)-没食子儿茶素(EGCg)的11种儿茶素代谢物被评估为抑制HeLa细胞增殖的活性，HeLa细胞是人宫颈癌细胞。在儿茶素代谢物中，1-(3,4,5-三羟基苯基)-3-(2,4,6-三羟基苯基)丙烷-2-醇(EGC-M2)、4-羟基-5-(3,4,5-三羟基苯基)戊酸(EGC-M7)和5-(3,4,5-三羟基苯基)戊酸(EGC-M9)被发现对HeLa细胞增殖有抑制活性，与对照组相比较。结果表明，苯环上的三个相邻羟基可能对抑制活性起重要作用。此外，用四种具有苯环上两个相邻羟基的(-)-表儿茶素(EC)代谢物检测抑制活性。只有5-(3,4-二羟基苯基)戊酸(EC-M9)显示抑制活性，因此戊酸部分可能对抑制活性有贡献。EGC-M9显示出最强的抑制活性，IC50为5.58µM。因此，在本研究中首次发现由EGC、EGCg和EC衍生的几种儿茶素代谢物抑制宫颈癌细胞增殖。
• General synthesis of epi-series catechins and their 3-gallates: reverse polarity strategy
  作者：Ken Ohmori、Takahisa Yano、Keisuke Suzuki

  DOI：10.1039/c003464a

  日期：——

  A general synthetic route to the epi-series catechins was developed based on the reverse polarity strategy. Aromatic nucleophilic substitution reaction followed by the sulfinyl–metal exchange and cyclization enabled stereo-controlled access to various members of epi-series catechins and their 3-gallates.

  基于反极性策略，开发了一条合成表儿茶素类化合物的通用合成路线。通过芳香族亲核取代反应、亚磺酰基-金属交换及环化反应，实现了多种表儿茶素及其3-没食子酸酯的立体控制合成。