4-(烯丙氧基)-3-乙氧基苯甲醛 | 225939-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(烯丙氧基)-3-乙氧基苯甲醛
• 中文别名: 3-乙氧基-4-丙-2-烯氧基-苯甲醛；3-乙氧基-4-丙-2-烯氧基苯甲醛
• 英文名称: 4-(allyloxy)-3-ethoxybenzaldehyde
• 英文别名: 4-allyloxy-3-ethoxybenzaldehyde；3-ethoxy-4-prop-2-enoxybenzaldehyde
• CAS: 225939-36-6
• 化学式: C₁₂H₁₄O₃
• mdl: MFCD02254126
• 分子量: 206.241
• InChiKey: JHYGKIUUKNSJTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2912499000

反应信息

• 作为反应物：
  描述：

  4-(烯丙氧基)-3-乙氧基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 80.0h， 生成
  参考文献：
  名称：

  作为非天然氨基酸前体的新型异恶唑烷-缩氨基硫脲杂化衍生物的合成和表征

  摘要：

  DOI：

  10.21608/ejchem.2022.111980.5088
• 作为产物：
  描述：

  乙基香兰素 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 4-(烯丙氧基)-3-乙氧基苯甲醛
  参考文献：
  名称：

  Design, economical synthesis and antiplasmodial evaluation of vanillin derived allylated chalcones and their marked synergism with artemisinin against chloroquine resistant strains of Plasmodium falciparum

  摘要：

  The in vitro blood stage antiplasmodial activity of a series of allylated chalcones based on the licochalcone A as lead molecule was investigated against chloroquine (CQ) sensitive Pf3D7 and CQ resistant PfINDO strains of Plasmodium falciparum using SYBR Green I assay. Of the forty two chalcones tested, eight showed IC50 < 5 mu M. Structure-activity relationship (SAR) studies revealed 9 {1-(4-Chlorophenyl)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl]-prop-2-en-1-one} as the most potent (IC50: 2.5 mu M) against Pf3D7 with resistance indices of 1.2 and 6.6 against PfDd2 and PfINDO strains, respectively. Later on, the synergistic effects 9 with standard antimalarials fartemisinin (ART) and chloroquine (CQ)} were studied in order to provide the basis for the selection of the best partner drug. In vitro combinations of 9 with ART showed strong synergy against PfINDO (Sigma FIC50: 0.31-0.72) but additive to slight antagonistic effects (Sigma FIC50: 1.97-2.64) against Pf3D7. Sigma FIC50 0.31 of ART+9 combination corresponded to a 320 fold and 3 fold reduction in IC50 of 9 and ART, respectively. Similar combinations of 9 with CQ showed synergy to additivity to mild antagonism against the two strains {Sigma FIC50: 0.668-2269 (PfINDO); 1.45-2.83 (Pf3D7)}. Drug exposure followed by drug withdrawal indicated that 9 taken alone at IC100 killed rings, trophozoites and schizonts of P. falciparum. The combination of ART and 9 (1X Sigma FIC100) selectively inhibited the growth of rings while the 2X Sigma FIC100 combination of the same caused killing of rings without affecting trophozoites and schizonts. In contrast, the 1x combination of CQ and 9 (Sigma FIC100: 0.5) killed rings and trophozoites. DNA fragmentation and loss of mitochondrial membrane potential (Delta Psi m) in the 9 treated P. falciparum culture indicated apoptotic death in malaria parasites. Prediction of ADME properties revealed that most of the molecules did not violate Lipinski's parameters and have low TPSA value suggesting good absorption. The results suggest the promising drug-like properties of 9 against CQ resistant Pf and propensity for synergy with classical antimalarial drugs together with easy and economical synthesis. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.079

文献信息

• New fluorescent trans-dihydrofluoren-3-ones from aldol–Robinson annulation–regioselective addition involved one-pot reaction
  作者：Yingpeng Huo、Xu Qiu、Weiyan Shao、Jianing Huang、Yanjun Yu、Yinglin Zuo、Linkun An、Jun Du、Xianzhang Bu

  DOI：10.1039/c0ob00401d

  日期：——

  An unexpected discovery of new trans-4-acetyl-1,9-dimethyl-4,4a-dihydro-3H-fluoren-3-ones from one pot reactions of benzaldehydes and acetylacetone is described. The synthetic mechanism and stereochemistry were discussed. These new derivatives exhibit good fluorescent properties in solutions.

  描述了一种意外发现的新型trans-4-acetyl-1,9-dimethyl-4,4a-dihydro-3H-fluoren-3-酮，这些化合物是通过苯甲醛和乙酰乙酮的一锅法反应得到的。讨论了合成机制和立体化学。这些新衍生物在溶液中表现出良好的荧光特性。
• Novel 3′,5′-diprenylated chalcones inhibited the proliferation of cancer cells in vitro by inducing cell apoptosis and arresting cell cycle phase
  作者：Zhonghang Wen、Yongqiang Zhang、Xinghui Wang、Xiaoping Zeng、Zhanxing Hu、Yi Liu、Yuxin Xie、Guangyi Liang、Jianguo Zhu、Heng Luo、Bixue Xu

  DOI：10.1016/j.ejmech.2017.03.077

  日期：2017.6

  PC3 prostate cancer cells, MDA-MB-231 breast cancer cells (MDA), HEL and K562 erythroleukemia cells with IC50 values of 2.92, 3.14, 1.85 and 2.64 μM, respectively. Further studies indicated that compound 10 induced apoptosis and arrested the cell cycle phase of the above mentioned four cancer cell lines. By contrast, compound 6g selectively displayed potent inhibitory activity against the proliferation

  建立了双重克莱森重排合成策略，用于4,4'-二甲基药物生成素的全合成（化合物6c）。还制备了一系列类似物，包括两个新颖的3'，5'-二戊烯基化的查耳酮，其中的B环被氮杂杂环取代。通过1 H NMR，13 C NMR和ESI-MS确认了22种新合成的化合物的结构。在体外，使用癌细胞评估了目标化合物的细胞毒性。值得注意的是，化合物10对PC3前列腺癌细胞，MDA-MB-231乳腺癌细胞（MDA），HEL和K562红白血病细胞表现出广谱细胞毒性，其IC50值分别为2.92、3.14、1.85和2.64μM。进一步的研究表明，化合物10诱导了上述四种癌细胞系的凋亡并使其停滞。相比之下，化合物6g选择性显示出对HEL细胞增殖的有效抑制活性，IC50值为4.35μM。化合物6g轻微诱导了HEL细胞的凋亡和停滞的细胞周期阶段。初步的构效关系研究表明，在所有评估的癌细胞系中，3​​-吡啶基对细胞毒性至关重要。
• AGENT FOR DYEING KERATIN-BASED FIBERS
  申请人：GROSS Wibke

  公开号：US20080104772A1

  公开（公告）日：2008-05-08

  An agent for dyeing keratin-containing fibers, especially human hair, is comprised of a cosmetic carrier, and (A) at least one compound of Formula I, wherein each of R 1 , R 2 and R 3 is independently a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a hydroxyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 hydroxyalkyl group, a C 2 -C 6 polyhydroxyalkyl group, a hydroxy C 1 -C 6 alkyloxy group, a sulfonyl group, a carboxyl group, a C 1 -C 6 alkoxycarbonyl group, a hydroxy C 2 -C 6 alkyloxycarbonyl group, a sulfonic acid group, a sulfonamido group, a sulfonamide group, a C 2 -C 6 acyl group, a formyl group, a nitro group, a carbamoyl group —C(O)—NR 4 R 5 , or a —(CH 2 ) n NR 6 R 7 group wherein each of R 4 , R 5 , R 6 and R 7 is independently a hydrogen atom, a C 1 -C 6 alkyl group or a C 2 -C 6 hydroxyalkyl group; and n is number from 0 to 6, wherein R 1 and R 2 can form a 5- or 6-membered aromatic or heteroaromatic ring; and (B) at least one CH-acidic compound.

  一种用于染色角蛋白质含量纤维，特别是人类头发的剂型，包括一个化妆品载体和(A)至少一种式子I的化合物，其中R1、R2和R3各自独立地是氢原子、卤素原子、C1-C6烷基、C2-C6烯基、羟基、C1-C6烷氧基、C1-C6羟基烷基、C2-C6多羟基烷基、羟基C1-C6烷氧基、磺酰基、羧基、C1-C6烷氧羰基、羟基C2-C6烷氧羰基、磺酸基、磺酰胺基、磺酰胺基、C2-C6酰基、甲酰基、硝基、氨基甲酰基-C(O)-NR4R5，或-（CH2）nNR6R7基团，其中R4、R5、R6和R7各自独立地是氢原子、C1-C6烷基或C2-C6羟基烷基；n是0到6的数字，在此R1和R2可以形成5-或6-成员的芳香或杂芳环；和（B）至少一种CH-酸性化合物。
• Agent for dyeing keratin-based fibers
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：US07393367B2

  公开（公告）日：2008-07-01

  An agent for dyeing keratin-containing fibers, especially human hair, is comprised of a cosmetic carrier, and (A) at least one compound of Formula I, wherein each of R1, R2 and R3 is independently a hydrogen atom, a halogen atom, a C1-C6 alkyl group, a C2-C6 alkenyl group, a hydroxyl group, a C1-C6 alkoxy group, a C1-C6 hydroxyalkyl group, a C2-C6 polyhydroxyalkyl group, a hydroxy C1-C6 alkyloxy group, a sulfonyl group, a carboxyl group, a C1-C6 alkoxycarbonyl group, a hydroxy C2-C6 alkyloxycarbonyl group, a sulfonic acid group, a sulfonamido group, a sulfonamide group, a C2-C6 acyl group, a formyl group, a nitro group, a carbamoyl group —C(O)—NR4R5, or a —(CH2)nNR6R7 group wherein each of R4, R5, R6 and R7 is independently a hydrogen atom, a C1-C6 alkyl group or a C2-C6 hydroxyalkyl group; and n is number from 0 to 6, wherein R1 and R2 can form a 5- or 6-membered aromatic or heteroaromatic ring; and (B) at least one CH-acidic compound.

  含角蛋白纤维染色剂的代理剂，特别是用于人类头发的，包括化妆品载体和（A）至少一种式I的化合物，其中R1、R2和R3中的每一个独立地是氢原子、卤素原子、C1-C6烷基、C2-C6烯基、羟基、C1-C6烷氧基、C1-C6羟基烷基、C2-C6多羟基烷基、羟基C1-C6烷氧基、磺酰基、羧基、C1-C6烷氧羰基、羟基C2-C6烷氧羰基、磺酸基、磺酰胺基、磺酰胺基、C2-C6酰基、甲酰基、硝基、氨基甲酰基-C(O)-NR4R5、或-(CH2)nNR6R7基，其中R4、R5、R6和R7中的每一个独立地是氢原子、C1-C6烷基或C2-C6羟基烷基；n是0到6的数字，其中R1和R2可以形成5-或6-成员芳香族或杂芳族环；和（B）至少一种CH-酸性化合物。
• Multifunctional isoxazolidine derivatives as α-amylase and α-glucosidase inhibitors
  作者：Ameni Ghabi、Jihed Brahmi、Fahad Alminderej、Sabri Messaoudi、Sébastien Vidal、Adel Kadri、Kaïss Aouadi

  DOI：10.1016/j.bioorg.2020.103713

  日期：2020.5

  A series of novel isoxazolidines based on benzaldehyde derivatives have been synthesized from the cycloaddition of chiral menthone-based nitrone and allyl phenyl ethers. All synthetic compounds were assessed for their in vitro PPA, HPA and HLAG inhibitory activity. The results revealed that all targets exhibited better inhibitory effect against PPA (12.3 +/- 0.4 < IC50 < 38.2 +/- 0.9 mu M), HPA (10.1 +/- 0.4 < IC50 < 26.8 +/- 0.2 mu M) and HLAG (65.4 +/- 1.2 < IC50 < 274.8 +/- 1.1 mu M) when compared with the reference inhibitor, acarbose (IC50 = 284.6 +/- 0.3 mu M for PPA, 296.6 +/- 0.8 mu M for HPA, 780.4 +/- 0.3 mu M for HLAG) with the highest PPA inhibitory activity was ascribed to compound 3g against both PPA and HPA, and 3b against HLAG enzymes, respectively. Structural activity relationships (SARs) were also established for all synthesized compounds and the interaction modes of the most potent inhibitors (3g for PPA and HPA, 3b for HLAG) and the active site with residues of three enzymes were confirmed through molecular docking studies. Furthermore, a combination of molecular docking analysis with the in vitro activities can help to improve prediction success and encourages the uses of some of these molecules as potential alternatives toward the modulation of T2D.