1-(2,4,6-tris(benzyloxy)phenyl)ethan-1-one | 61497-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,4,6-tris(benzyloxy)phenyl)ethan-1-one
• 英文别名: 1-[2,4,6-Tris(benzyloxy)phenyl]ethan-1-one；1-[2,4,6-tris(phenylmethoxy)phenyl]ethanone
• CAS: 61497-71-0
• 化学式: C₂₉H₂₆O₄
• 分子量: 438.523
• InChiKey: UFEIUCLPZWZVBM-UHFFFAOYSA-N

物化性质

• 沸点：
  622.5±50.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1-(2,4,6-tris(benzyloxy)phenyl)ethan-1-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以84%的产率得到2-乙酰基-3,5-双(苄氧基)苯酚
  参考文献：
  名称：

  Synthesis and antiproliferative activity of benzofuran-based analogs of cercosporamide against non-small cell lung cancer cell lines

  摘要：

  A novel series of 3-methyl-1-benzofuran derivatives were synthesized and screened in vitro for their antiproliferative activity against two human NSCLC cell lines (NSCLC-N6 mutant p53 and A549 wild type p53). Most promising compounds presented a structural analogy with the west part of cercosporamide, a natural product of biological interest. In particular, compounds 10, 12 and 31 showed cytotoxic activities at micromolar concentrations (IC50 < 9.3 mu M) and compounds 13, 18 and 32 displayed moderate ICso values (25-40 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.013
• 作为产物：
  描述：

  间苯三酚 在 吡啶 、 水 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 22.5h， 生成 1-(2,4,6-tris(benzyloxy)phenyl)ethan-1-one
  参考文献：
  名称：

  Synthesis and antiproliferative activity of benzofuran-based analogs of cercosporamide against non-small cell lung cancer cell lines

  摘要：

  A novel series of 3-methyl-1-benzofuran derivatives were synthesized and screened in vitro for their antiproliferative activity against two human NSCLC cell lines (NSCLC-N6 mutant p53 and A549 wild type p53). Most promising compounds presented a structural analogy with the west part of cercosporamide, a natural product of biological interest. In particular, compounds 10, 12 and 31 showed cytotoxic activities at micromolar concentrations (IC50 < 9.3 mu M) and compounds 13, 18 and 32 displayed moderate ICso values (25-40 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.013

文献信息

• Concise Total Syntheses of Aspalathin and Nothofagin
  作者：Akop Yepremyan、Baback Salehani、Thomas G. Minehan

  DOI：10.1021/ol100315g

  日期：2010.4.2

  Syntheses of the C-glycosyl flavone natural products aspalathin and nothofagin have been accomplished in eight steps from tribenzyl glucal, tribenzylphloroglucinol, and either 4-(benzyloxy)phenylacetylene or 3,4-bis(benzyloxy)phenylacetylene. The key step of the syntheses involves a highly stereoselective Lewis acid promoted coupling of 1,2-di-O-acyl-3,4,6-tribenzylglucose with tribenzylphloroglucinol

  C-糖基黄酮天然产物天冬酰胺和诺夫他汀的合成已由三苄基葡萄糖，三苄基间苯三酚和4-（苄氧基）苯乙炔或3,4-双（苄氧基）苯乙炔以八步完成。合成的关键步骤涉及高度立体选择性的路易斯酸促进1,2-二-O-酰基-3,4,6-三苄基葡萄糖与三苄基间苯三酚的偶联，从而在30-中产生相应的β- C-芳基糖苷65％的产率。
• Total Synthesis of (±)-Isoperbergins and Correction of the Chemical Structure of Perbergin
  作者：Khaled H. Almabruk、Jeff H. Chang、Taifo Mahmud

  DOI：10.1021/acs.jnatprod.6b00621

  日期：2016.9.23

  On the basis of its reported chemical structure, perbergin, a Rhodococcus fascians virulence quencher from the bark of Dalbergia pervillei, and its isomer were synthesized in nine steps with a 13.5% yield. However, the NMR spectra of the synthetic products were inconsistent with those reported in the literature. Re-evaluation of the 1D and 2D NMR spectra of the natural product perbergin revealed that

  在其报告的化学结构，perbergin，一个基础红球菌fascians从树皮的毒性淬灭剂黄檀pervillei，及其同分异构体在九个步骤，收率13.5％合成。但是，合成产物的NMR谱与文献报道的不一致。天然产物perbergin的1D和2D NMR谱图的重新评估表明，该化合物的香叶基部分位于C-6并具有E-构型，而不是报道的Z -8构型的C-8 geranyation 。有趣的是，合成的isoperbergins表现出良好的抗菌活性对R. fascians，耻垢分枝杆菌，并金黄色葡萄球菌，但不针对革兰氏阴性菌铜绿假单胞菌和大肠杆菌。
• Sulfoalkylated flavanone sweeteners
  申请人：Dynapol Corporation

  公开号：US04025535A1

  公开（公告）日：1977-05-24

  Flavanones represented by the formula ##STR1## wherein R is a lower alkyl of from one to three carbon atoms inclusive, n is an integer of from one to three inclusive and M is hydrogen or a physiologically acceptable metal cation, are disclosed. These materials are themselves useful as dietetic sweeteners as well as being direct intermediates for the preparation of useful dihydrochalcone sweeteners.

  公式表示的类黄酮##STR1##，其中R是由一到三个碳原子组成的较低烷基，n是从一到三的整数，M是氢或生理上可接受的金属阳离子。这些物质本身可用作膳食甜味剂，同时也可作为有用的二氢黄酮甜味剂的直接中间体。
• Synthesis of 4-<i>C</i> -β-D-Glucosylated Isoliquiritigenin and Analogues for Aldose Reductase Inhibition Studies
  作者：Mannem Rajeswara Reddy、Indrapal Singh Aidhen、Utkarsh A. Reddy、Geereddy Bhanuprakash Reddy、Kundane Ingle、Sami Mukhopadhyay

  DOI：10.1002/ejoc.201900413

  日期：2019.6.30

  natural product isoliquiritigenin (ISL), to enhance the bioavailability of ISL, 4‐C‐glucosylated isoliquiritigenin and several C‐glucosylated chalcones have been synthesized and evaluated for aldose reductase (AR) inhibition activity. Excellent AR inhibition has been observed with C‐glucosylated ISL with IC50 value of 21 µM which is similar to the chalcone ISL (IC50 of 19 µM). The studies have revealed

  为了提高ISL的生物利用度，从天然产物异寡糖原蛋白（ISL）中获得启发，合成了4 C葡萄糖基化异黄酮苷原和几种C葡糖基化查耳酮，并对其醛糖还原酶（AR）抑制活性进行了评估。C葡萄糖基化的ISL的IC 50值为21 µM，与查尔酮ISL相似（IC 50为19 µM），观察到了出色的AR抑制作用。研究表明，很少有具有希望的活性的新类似物。
• 一种非葡萄糖碳苷二氢查尔酮及其制备方法
  申请人：北京理工亘舒科技有限公司

  公开号：CN110078774A

  公开（公告）日：2019-08-02

  本发明提供了一种非葡萄糖碳苷二氢查尔酮，其特征在于，所述非葡萄糖碳苷二氢查尔酮为具有下述通式Ⅰ的化合物，或所述非葡萄糖碳苷二氢查尔酮为具有所述通式Ⅰ的化合物与无机酸或有机酸形成的可接受的盐；其中，所述通式Ⅰ中，A包括双糖基、单糖基中的任意一种；所述单糖基包括除葡萄糖基外的单糖基；R代表的取代基包括1‑4元烷基、卤素取代的1‑4元烷基、3‑4元烯基、3‑4元炔基、3‑6元环烷基、卤素取代的3‑6元环烷基中的任意一种。本发明实施例中所提供的非葡萄糖碳苷二氢查尔酮，能够在低毒副作用下，加快降血糖的起效时间，有效改善糖尿病患者的糖耐量。