3-甲氧基-4-(3-羟基丙氧基)苯甲醛 | 107115-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲氧基-4-(3-羟基丙氧基)苯甲醛
• 英文名称: 3-methoxy-4-(3-hydroxypropoxy)benzaldehyde
• 英文别名: 4-(3-hydroxypropoxy)-3-methoxybenzaldehyde
• CAS: 107115-25-3
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: PUMLXXYKLDBPTI-UHFFFAOYSA-N

物化性质

• 沸点：
  365.7±27.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲氧基-4-(3-羟基丙氧基)苯甲醛 以 乙醇 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 (Z)-5-[4-(3-hydroxypropoxy)-3-methoxybenzylidene]-3-cyclohexyl-1-[(4-methylpiperazin-1-yl)-methyl]-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  带有2-硫代氧杂咪唑啉丁-4-酮部分的一些新的S-烷基化和曼尼希碱的合成与表征

  摘要：

  在本研究中，两个新的4- [4-（3-羟基丙氧基）-3-甲氧基亚苄基] -1-（3-氯苯基）-2-（烷硫基）-1 H-咪唑-5（4 H）-系列通过与一些卤代无环烃经S-烷基化反应和合成三个[5-（4-（3-羟基丙氧基）-3-甲氧基亚苄基] -3-环己基-1-（取代的氨基甲基）-2-硫代氧杂咪唑啉-4-酮-组分曼尼希反应（MCR）。S-烷基化的2-硫代乙内酰脲和曼尼希碱均通过IR，NMR，质谱数据和元素分析表征。

  DOI：

  10.1134/s1070363215120312
• 作为产物：
  描述：

  3-氯-1-丙醇 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以72%的产率得到3-甲氧基-4-(3-羟基丙氧基)苯甲醛
  参考文献：
  名称：

  二氧化硅包覆的Fe 3 O 4上负载的含双茂铁的离子液体：新型的合成二氢吡喃并[2,3- c ]香豆素衍生物的纳米磁性催化剂

  摘要：

  以新型的多相催化剂为载体，在二氧化硅包覆的Fe 3 O 4（Fe 3 O 4 @SiO 2 @咪唑-bisFc [HCO 3 ]）上负载了含纳米磁性双二茂铁的离子液体，并通过傅里叶表征了纳米磁性催化剂的结构和形貌。变换红外光谱（FT-IR），能量色散X射线光谱（EDX），X射线衍射图（XRD），扫描电子显微镜（SEM），透射电子显微镜（TEM），差示扫描量热法（DSC）和热重分析（TGA）。 发现该新合成的催化剂是在无溶剂条件下通过各种芳族醛，丙二腈和4-羟基香豆素的一锅三组分缩合反应合成二氢吡喃并[2,3- c ]香豆素衍生物的有效纳米催化剂。通过1 H NMR，13 C NMR，FT-IR和CHNS分析鉴定吡喃香豆素产物。该新方法具有显着的优点，例如操作简单，产率高，反应时间短，易于后处理，环保且无毒的催化剂。同样，该催化剂可以很容易地通过外部磁场回收，并且可以连续六个反应周期重复使用，而不会显着降低活性。

  DOI：

  10.1016/j.jorganchem.2018.06.007

文献信息

• [EN] HYDRAZONE COMPOUNDS AND THEIR USE<br/>[FR] COMPOSÉS D'HYDRAZONE ET LEUR UTILISATION
  申请人：STEIN PHILIP

  公开号：WO2010132615A1

  公开（公告）日：2010-11-18

  The present invention relates to hydrazone compounds of Formula I: (I) and pharmaceutically acceptable salts and stereoisomers thereof, wherein R1, R2, R3, R4, L1, and L2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I as inhibitors of TRPM5 protein.

  本发明涉及式I的腙化合物：(I)及其药用可接受的盐和立体异构体，其中R1、R2、R3、R4、L1和L2的定义如规范中所述。该发明还涉及将式I的化合物用作TRPM5蛋白的抑制剂。
• Fe ₃ O ₄ <i>@</i> SiO ₂ <i>@</i> Im‐bisethylFc [HC ₂ O ₄ ] as a novel recyclable heterogeneous nanocatalyst for synthesis of bis‐coumarin derivatives
  作者：Reza Teimuri‐Mofrad、Shabnam Tahmasebi、Elmira Payami

  DOI：10.1002/aoc.4773

  日期：2019.6

  Nanomagnetic bisethylferrocene‐containing ionic liquid supported on silica‐coated iron oxide (Fe3O4@SiO2@Im‐bisethylFc [HC2O4]) as a novel catalyst was designed and synthesized. The described catalyst was recycled and used without change in the time and efficiency of the condensation reaction. The Fourier transform‐infrared spectroscopy (FT‐IR), scanning electron microscopy images, X‐ray diffraction

  设计并合成了负载在二氧化硅包覆的氧化铁上的纳米磁性双乙基二茂铁离子液体（Fe 3 O 4 @ SiO 2 @ Im-bisethylFc [HC 2 O 4 ]）。所描述的催化剂被循环使用并且在不改变缩合反应的时间和效率的情况下使用。傅里叶变换红外光谱（FT-IR），扫描电子显微镜的图像，X射线衍射图案，能量色散型X射线光谱法，透射型电子显微镜和振动样品磁强计结果证实形成Fe 3 ö 4 @的SiO 2 @ Im‐bisethylFc [HC2 O 4 ]磁性纳米粒子。通过1 H-NMR，13 C-NMR，FT-IR和CHNS分析鉴定了新型双香豆素衍生物。
• Hydrazone Compounds and Their Use
  申请人：STEIN Philip

  公开号：US20110033393A1

  公开（公告）日：2011-02-10

  The present invention relates to hydrazone compounds of Formula I: and pharmaceutically acceptable salts and stereoisomers thereof, wherein R 1 , R 2 , R 3 , R 4 , L 1 , and L 2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I as inhibitors of TRPM5 protein.

  本发明涉及式I的腙化合物及其药用可接受的盐和立体异构体，其中R1、R2、R3、R4、L1和L2的定义如规范中所述。本发明还涉及将式I的化合物用作TRPM5蛋白质的抑制剂。
• Unsymmetrical DNA Cross-Linking Agents:  Combination of the CBI and PBD Pharmacophores
  作者：Moana Tercel、Stephen M. Stribbling、Hilary Sheppard、Bronwyn G. Siim、Kent Wu、Susan M. Pullen、K. Jane Botting、William R. Wilson、William A. Denny

  DOI：10.1021/jm020526p

  日期：2003.5.1

  A set of 10 compounds, each combining the seco-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (seco-CBI) and pyrrolo[2,1-c][1,4]benzodiazepine (PBD) pharmacophores, was designed and prepared. These compounds were anticipated to cross-link between N3 of adenine and N2 of guanine in the minor groove of DNA. The compounds, which differ in the chain length separating the two alkylation subunits, and the configuration of the CBI portion, showed great variation in cellular toxicity (over 4 orders of magnitude in a cell line panel) with the most potent example exhibiting IC50S in the pM range. Cytotoxicity correlated with the ability of the compounds to cross-link naked DNA. Cross-linking was also observed in living cells, at much lower concentrations than for a related symmetrical PBD dimer. A thermal cleavage assay was used to assess sequence selectivity, demonstrating that the CBI portion controlled the alkylation sites, while the PBD substituent increased the overall efficiency of alkylation. Several compounds were tested for in vivo activity using a tumor growth delay assay against WiDr human colon carcinoma xenografts, with one compound (the most cytotoxic and most efficient cross-linker) showing a statistically significant increase in survival time following a single iv dose.
• Target Guided Synthesis of 5-Benzyl-2,4-diamonopyrimidines: Their Antimalarial Activities and Binding Affinities to Wild Type and Mutant Dihydrofolate Reductases from <i>Plasmodium falciparum</i>
  作者：Chawanee Sirichaiwat、Chakapong Intaraudom、Sumalee Kamchonwongpaisan、Jarunee Vanichtanankul、Yodhathai Thebtaranonth、Yongyuth Yuthavong

  DOI：10.1021/jm0303352

  日期：2004.1.1

  The resistance to pyrimethamine (PYR) of Plasmodium falciparum arising from mutation at position 108 of dihydrofolate reductase (pfDHFR) from serine to asparagine (S108N) is due to steric interaction between the bulky side chain of N108 and Cl atom of the 5-p-Cl aryl group of PYR, which consequently resulted in the reduction in binding affinity between the enzyme and inhibitor. Molecular modeling suggested that the flexible antifolate, such as trimethoprim (TMP) derivatives, could avoid this steric constraint and should be considered as new, potentially effective compounds. The hydrophobic interaction between the side chain of inhibitor and the active site of the enzyme around position 108 was enhanced by the introduction of a longer and more hydrophobic side chain on TMP's 5-benzyl moiety. The prepared compounds, especially those bearing aromatic substituents, exhibited better binding affinities to both wild type and mutant enzymes than the parent compound. Binding affinities of these compounds correlated well with their antimalarial. activities against both wild type and resistant parasites. Molecular modeling of the binding of such compounds with pfDHFR also supported the experimental data and clearly showed that aromatic substituents play an important role in enhancing binding affinity. In addition, some compounds with 6-alkyl substituents showed relatively less decrease in binding constants with the mutant enzymes and relatively good antimalarial. activities against the parasites bearing the mutant enzymes.