3-octyloxyacetophenone | 37065-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-octyloxyacetophenone
• 英文别名: 3-n-octyloxy acetophenone；1-[3-(Octyloxy)phenyl]ethanone；1-(3-octoxyphenyl)ethanone
• CAS: 37065-52-4
• 化学式: C₁₆H₂₄O₂
• mdl: MFCD11542721
• 分子量: 248.365
• InChiKey: FBSPOTOXGJNKPH-UHFFFAOYSA-N

物化性质

• 沸点：
  345.9±15.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.562
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-octyloxyacetophenone 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Non-symmetric dimers comprising chalcone and cholesterol entities: an investigation on structure–property correlations

  摘要：

  非对称手性二聚体由香豆素和胆固醇单元组成，已经制备并研究了它们的结构性质关系。

  DOI：

  10.1039/c4nj00426d
• 作为产物：
  描述：

  1-溴辛烷 、 3-羟基苯乙酮 在 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 12.0h， 以80%的产率得到3-octyloxyacetophenone
  参考文献：
  名称：

  Non-symmetric dimers comprising chalcone and cholesterol entities: an investigation on structure–property correlations

  摘要：

  非对称手性二聚体由香豆素和胆固醇单元组成，已经制备并研究了它们的结构性质关系。

  DOI：

  10.1039/c4nj00426d

文献信息

• Design, Synthesis, Biological Evaluation and Inhibition Mechanism of 3-/4-Alkoxy Phenylethylidenethiosemicarbazides as New, Potent and Safe Tyrosinase Inhibitors
  作者：Senchuan Song、Yuliang Mai、Huahong Shi、Bing Liao、Fei Wang

  DOI：10.1248/cpb.c19-00949

  日期：2020.4.1

  Tyrosinase plays important roles in many different disease related processes, and the development of its inhibitors is particularly important in biotechnology. In this study, thirty-nine 3-/4-alkoxyphenylethylidenethiosemicarbazides were synthesized as novel tyrosinase inhibitors based on structure-based molecular design. Our experimental results demonstrated that thirty-one of them possess remarkable tyrosinase inhibitory activities with IC50 value below 1 µM, and 5a, 6e, 6g and 6t did not display any toxicity to 293T cell line at the concentration of 1000 µmol/L. According to the inhibitory activities, several compounds were selected for detail investigation on the structure–activity relationships (SARs), mechanisms of enzyme inhibition, inhibitory kinetics and cytotoxicity. In particular, the interaction between the selected inhibitors and the active center of tyrosinase was considered and discussed in detail based on their structural characteristics. Taken together, the results presented here demonstrated that the newly designed compounds are promising candidates for the treatment of tyrosinase-related disorders and further development of them may have significant contribution in biomedical science.

  酪氨酸酶在多种与疾病相关的过程中扮演重要角色，其抑制剂的研发在生物技术领域尤为重要。本研究基于结构导向的分子设计，合成了39种新颖的3-/4-烷氧基苯乙烯基二唑半卡巴唑类化合物作为酪氨酸酶抑制剂。我们的实验结果显示，其中31种化合物的酪氨酸酶抑制活性显著，IC50值低于1µM，且5a、6e、6g和6t在1000µmol/L浓度下对293T细胞系无毒性。根据抑制活性，选取了若干化合物详细研究了构效关系、酶抑制机制、抑制动力学及细胞毒性。特别是，基于这些化合物的结构特征，详细考虑并讨论了所选抑制剂与酪氨酸酶活性中心的相互作用。综上所述，本研究结果表明，新设计的化合物是治疗与酪氨酸酶相关疾病的潜在候选药物，其进一步开发可能对生物医学科学产生重大贡献。
• Reactivity in Micelles - Are We Really Able to Design Micellar Catalysts?
  作者：Radek Jurok、Eva Svobodová、Radek Cibulka、František Hampl

  DOI：10.1135/cccc20080127

  日期：——

  Coordination of lipophilic alkyl pyridin-2-yl ketoximes 1 to Ni²⁺ ions, reduction of lipophilic 3-alkoxyacetophenones 2 with sodium borohydride, and alkaline hydrolysis of 4-nitrophenyl diphenyl phosphate (PNPDPP) were employed as probes in the investigation which factors may influence the reactivity of organic compounds in micellar systems. In all these reactions, a lipophilic substrate solubilized in micellar core was attacked by a hydrophilic reagent from the bulk aqueous phase. To evaluate the contribution of electrostatic interactions between the micellar surface charge and the reagent to the observed reactivity, we combined reactions involving the reagents with opposite polarity (Ni²⁺ cations and borohydride or hydroxide anions) with positively charged micelles of hexadecyltrimethylammonium chloride (CTAC) or bromide (CTAB) and negatively charged micelles of sodium dodecyl sulfate (SDS). Non-ionic micelles (Triton X-100 or Brij 35) served as a reference. The results of the kinetic studies give evidence that each of the investigated systems has unique properties going in particular aspects beyond the scope of the generally accepted concepts of reactivity in micelles.

  脂溶性烷基吡啶-2-酮肟1与Ni2+离子的配位，脂溶性3-烷氧基苯乙酮2与硼氢化钠的还原反应，以及对硝基苯基二苯酚磷酸酯（PNPDPP）的碱性水解被用作探究哪些因素可能影响胶束系统中有机化合物的反应性的探针。在所有这些反应中，溶解在胶束核心中的脂溶性底物被来自大量水相的亲水试剂攻击。为了评估胶束表面电荷与试剂之间静电相互作用对观察到的反应性的贡献，我们结合了涉及相反极性试剂（Ni2+阳离子和硼氢化物或氢氧根阴离子）的反应与十六烷基三甲基溴化铵（CTAC）或氯化铵（CTAB）的带正电的胶束以及十二烷基硫酸钠（SDS）的带负电的胶束。非离子胶束（Triton X-100或Brij 35）作为参考。动力学研究结果表明，每个研究系统都具有独特的特性，特别是在某些方面超出了胶束中反应性的通常接受概念的范围。
• Sadashiva, Bukkinakere K.; Prasad, Veena, Journal of the Chemical Society. Perkin transactions II, 1996, # 4, p. 755 - 760
  作者：Sadashiva, Bukkinakere K.、Prasad, Veena

  DOI：——

  日期：——
• Veber, M.; Jallabert, C.; Strzeleska, H., Synthetic Communications, 1987, vol. 17, # 6, p. 693 - 702
  作者：Veber, M.、Jallabert, C.、Strzeleska, H.

  DOI：——

  日期：——
• Gionis; Fugnitto; Strzelecka, Molecular Crystals and Liquid Crystals (1969-1991), 1983, vol. 95, # 3-4, p. 351 - 358
  作者：Gionis、Fugnitto、Strzelecka、Le Barny

  DOI：——

  日期：——