3-hydroxy-2,4-dimethyl-benzaldehyde | 90535-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroxy-2,4-dimethyl-benzaldehyde
• 英文别名: 3-Hydroxy-2,4-dimethylbenzaldehyde
• CAS: 90535-99-2
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: OTIGZTVNVNDUNV-UHFFFAOYSA-N

物化性质

• 熔点：
  117 °C
• 沸点：
  263.2±35.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2,4-dimethyl-benzaldehyde 在 氢氧化钾 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 甲醇 、 乙醇 、 水 、 苯 为溶剂， 反应 9.0h， 生成 3-benzyloxy-2,4-dimethylphenylacetonitrile
  参考文献：
  名称：

  Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

  摘要：

  Benzylimidazolines may represent a class of 5-HT1D ligands that has yet to be exploited. On the basis of a previous report that the 2-(substituted-benzyl)imidazoline alpha-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT1D receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT1D (i.e., human 5-HT1D alpha) receptors, this modification reduced h5-HT1B (i.e., human 5-HT1D beta) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT1B binding than h5-HT1D binding.With the appropriate structural modifications, several compounds were identified that display 20- to >100-fold selectivity for h5-HT1D versus h5-HT1B receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT1D agonists are currently being explored for their antimigraine action and that activation of h5-HT1B receptors might be associated with cardiovascular side effects, h5-HT1D-selective agents may offer a new lead for the development of therapeutically efficacious agents.

  DOI：

  10.1021/jm970513p
• 作为产物：
  描述：

  6α,8α-Dimethyl-1α-H, 2α-H, 4α-H, 5α-H-3,9-dioxatricyclo<3.3.1.0^2,4>nonan-7-on 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.25h， 以89%的产率得到3-hydroxy-2,4-dimethyl-benzaldehyde
  参考文献：
  名称：

  Baseninduzierte umlagerungen von 3,9 dioxatricyclo[3.3.1.02,4]nonan-7-onen zu m-hydroxyphenylcarbonyl-verbindungen

  摘要：

  DOI：

  10.1016/s0040-4020(01)96563-9

文献信息

• Design, Synthesis and Biological Evaluation of Some Novel Chalcones-sulphonamide Hybrids
  作者：Khanusiya, Mahammadali、Gadhawala, Zakirhusen

  DOI：10.5012/jkcs.2018.62.5.377

  日期：——

  A new class of Chalcone-Sulphonamide hybrids has been designed by condensing appropriate sulphonamide scaffold with substituted chalcones tethered by chloroacetyl chloride as a multi-target drug for therapeutic treatment. Chalcones were prepared by Claisen-Schmidt condensation of a substituted aldehyde with para aminoacetophenone. These Chalcone-Sulphonamide hybrids were screened by means of their antibacterial activity by NCCLS method. Among all these compounds, 5e and 5c displayed more potent growth inhibitory activity against Staphylococcus epidermidis and Pseudomonas aeruginosa bacteria respectively. Further, these hybrids were evaluated for their antifungal activity, among all hybrid 5a exhibited potent antifungal activity. The synthesized compounds were characterized by FT-IR, $^1HNMR$, $^13}CNMR$ and HR-LCMS and spectral study supports the structures of synthesized Chalcone-Sulphonamide hybrids.

  通过将适当的磺酰胺支架与氯乙酰氯拴住的取代查耳酮缩合，设计出了一类新的查耳酮-磺酰胺杂交化合物，作为多靶点治疗药物。查耳酮是通过取代醛与对氨基苯乙酮的克莱森-施密特缩合反应制备的。通过 NCCLS 方法对这些查耳酮-磺酰胺杂化物的抗菌活性进行了筛选。在所有这些化合物中，5e 和 5c 分别对表皮葡萄球菌和绿脓杆菌具有更强的生长抑制活性。此外，还对这些杂交化合物的抗真菌活性进行了评估，其中杂交化合物 5a 具有很强的抗真菌活性。通过傅立叶变换红外光谱（FT-IR）、$^1HNMR$、$^13}CNMR$和 HR-LCMS，对合成的化合物进行了表征。
• Beta-substitued beta-aminoethyl phosphonate derivatives
  申请人：——

  公开号：US20020111488A1

  公开（公告）日：2002-08-15

  The present invention relates to novel &bgr;-substituted-&bgr;-aminoethylphosphonate derivatives and their uses for lowering plasma levels of apo (a), Lp(a), apo B, apo B associated lipoproteins (low density lipoproteins and very low density lipoproteins) and for lowering plasma levels of total cholesterol.

  本发明涉及新型β-取代-β-氨基乙基膦酸酯衍生物及其用于降低血浆中apo（a）、Lp（a）、apo B、apo B相关脂蛋白（低密度脂蛋白和极低密度脂蛋白）水平和降低血浆总胆固醇水平的用途。
• Merchant,J.R.; Shetty,S.M., Journal of the Indian Chemical Society, 1968, vol. 45, # 10, p. 865 - 876
  作者：Merchant,J.R.、Shetty,S.M.

  DOI：——

  日期：——
• FOEHLISCH, B.;HERRSCHER, O., TETRAHEDRON, 1985, 41, N 10, 1979-1983
  作者：FOEHLISCH, B.、HERRSCHER, O.

  DOI：——

  日期：——
• BETA-SUBSTITUTED BETA-AMINOETHYL PHOSPHONATES
  申请人：Ilex Oncology Research S.A.

  公开号：EP1330463A2

  公开（公告）日：2003-07-30