4-benzyloxy-3,5-dimethoxybenzaldehyde | 119030-76-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-benzyloxy-3,5-dimethoxybenzaldehyde
• 英文别名: 4-benzoxy-3,5-dimethoxybenzaldehyde；(4-Formyl-2,6-dimethoxyphenyl) benzoate
• CAS: 119030-76-1
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: OMKLJHHYJMCACD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-3,5-dimethoxybenzaldehyde 在 六甲基磷酰三胺 、 sodium hydroxide 、 sodium tetrahydroborate 、 氢溴酸 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 30.5h， 生成 (+/-)-4'-O-Demethylyatein
  参考文献：
  名称：

  Burden, Jonathan K.; Cambie, Richard C.; Craw, Peter A., Australian Journal of Chemistry, 1988, vol. 41, # 6, p. 919 - 933

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲酰氯 、 丁香醛 在 三乙胺 作用下， 以 苯 为溶剂， 反应 15.0h， 以94%的产率得到4-benzyloxy-3,5-dimethoxybenzaldehyde
  参考文献：
  名称：

  Burden, Jonathan K.; Cambie, Richard C.; Craw, Peter A., Australian Journal of Chemistry, 1988, vol. 41, # 6, p. 919 - 933

  摘要：

  DOI：

文献信息

• Impact of reducing agent, temperature, and substrate topology on diastereoselectivity of the intermolecular coupling reactions, or how “free” are cobalt-complexed propargyl radicals?
  作者：Gagik G. Melikyan、Louis Carlson、Nare Sahakyan、Arthur Floruti、McKinzie Garrison

  DOI：10.1039/c3dt51502h

  日期：——

  Applicability of the term “free radical” to organometallic radicals was studied by using the stereoselectivity of radical C–C bond formation as a diagnostic tool. Based on diastereoselectivity data, it was concluded that the reduction of π-bonded, Co2(CO)6-complexed propargyl cations with heterogeneous reducing agents (Zn, Mg) generates “free radicals”, while homogeneous reductants (Cp2Co, Na–Ph2CO) produce “sequestered radicals”, presumably associated with reductant-derived oxidized species. The latter are comparable in molecular volume to the requisite radical species, thus restricting the motion and conformational freedoms of converging, transition metal-complexed propargyl radicals. Diastereoselectivity of intermolecular reactions is determined to be much less sensitive toward temperature variation (Δde = 6–22%) than in intramolecular radical cyclizations (Δde = 106%).

  通过利用自由基C-C键形成的立体选择性作为诊断工具，研究了术语“自由基”在有机金属自由基中的适用性。基于对映选择性数据，得出结论：当使用非均相还原剂（锌、镁）还原π键结合的、Co2(CO)6复合的炔丙基阳离子时，生成“自由基”，而均相还原剂（Cp2Co，Na-Ph2CO）则产生“隔离自由基”，这些自由基可能与还原剂衍生的氧化物种相关联。后者的分子体积与所需自由基物种相当，从而限制了汇聚型过渡金属复合炔丙基自由基的运动和构象自由。分子间反应的对映选择性对温度变化的敏感度远低于分子内自由基环化反应（Δde = 6-22% 对比 Δde = 106%）。
• Chemical synthesis, docking studies and biological effects of functionalized 1,3-diaryl-2-propen-1-ones on human colon cancer cells
  作者：Guo-Min Zhu、Guo-Dong Huang

  DOI：10.3329/bjp.v10i1.21699

  日期：——

  A series of 1, 3-diaryl-2-propen-1-ones was synthesised in order to obtain a new type of anticancer drug, designed with hybrid features to inhibit colon cancer activated receptor. Based on computational modelling and docking studies, potential inhibitors were synthesised and their biological activity evaluated. The structures of newly synthesized compounds were confirmed by 1HNMR, 13CNMR and Mass spectrometry. All analogues were evaluated for in vitro cytotoxicity against human colon (caco-2) cancer cell lines. Compounds 1b, 1f-1h, and 2i showed significant cytotoxicity. Chalcones 1b, 1f and 1g were identified as the most potent and selective anticancer agents with IC50 values <1 µg/mL and 1.5 µg/mL, against caco-2 cell line, respectively. In conclusion, this finding confirms the suitability of indolyl chalcone analogues as candidates for further investigation towards the management of colon cancer related diseases.

  为了获得一种新型抗癌药物，我们合成了一系列 1，3-二芳基-2-丙烯-1-酮，其设计具有抑制结肠癌活化受体的混合特征。在计算建模和对接研究的基础上，合成了潜在的抑制剂，并对其生物活性进行了评估。新合成化合物的结构通过 1HNMR、13CNMR 和质谱进行了确认。评估了所有类似物对人结肠癌（caco-2）细胞系的体外细胞毒性。化合物 1b、1f-1h 和 2i 显示出显著的细胞毒性。查耳酮 1b、1f 和 1g 被确定为最有效的选择性抗癌剂，对 caco-2 细胞系的 IC50 值分别为 1 µg/mL 和 1.5 µg/mL。总之，这一发现证实了吲哚基查尔酮类似物适合作为进一步研究结肠癌相关疾病治疗的候选药物。
• Synthesis, molecular modelling studies of indolyl chalcone derivatives and their antimalarial activity evaluation
  作者：Jyoti、Rashmi Gaur、Yogesh Kumar、Harveer Singh Cheema、Deepak Singh Kapkoti、Mahendra P. Darokar、Feroz Khan、Rajendra Singh Bhakuni

  DOI：10.1080/14786419.2019.1696788

  日期：2021.10.2

  of terrestrial plants, precursors for the biosynthesis of flavonoids and exhibit various biological activities. Antiplasmodial IC50 (half-maximal inhibitory concentration) activity of a compound against malaria parasites in vitro provides a good first screen for identifying the antimalarial potential of the compound. The most active compound was Trans-3-(1H-indol-3-yl)-1-(2’-hydroxyphenyl)-2-propen-1-one

  摘要 使用 Claisen-Schmidt 缩合合成了 21 种查尔酮衍生物，测定了它们对恶性疟原虫的抗疟活性，并建立了定量构效关系 (QSAR)。取代苯乙酮与各种芳香醛在室温下缩合得到 75-96% 产率的查耳酮。查耳酮是陆生植物的次生代谢产物，是类黄酮生物合成的前体，具有多种生物活性。化合物在体外抗疟原虫的抗疟原虫IC 50（半数最大抑制浓度）活性为鉴定该化合物的抗疟潜力提供了良好的初步筛选。最活跃的化合物是Trans-3-(1H-indol-3-yl)-1-(2'-hydroxyphenyl)-2-propen-1-one (1b)，IC 50为 2.1 µM/L。通过对活性化合物的计算机对接和 ADMET 研究探索了分子机制。
• BURDEN, JONATHAN K.;CAMBIE, RICHARD C.;CRAW, PETER A.;RUTLEDGE, PETER S.;+, AUSTRAL. J. CHEM., 41,(1988) N 6, C. 919-933
  作者：BURDEN, JONATHAN K.、CAMBIE, RICHARD C.、CRAW, PETER A.、RUTLEDGE, PETER S.、+

  DOI：——

  日期：——
• SUBSTRATES FOR THE ASSAY OF ENZYMES
  申请人：KING'S COLLEGE LONDON

  公开号：EP0375723A1

  公开（公告）日：1990-07-04

表征谱图