methyl 8-oxo-8-(p-tolyl)octanoate | 91202-40-3

• 分子结构分类: 有机化合物
• 英文名称: methyl 8-oxo-8-(p-tolyl)octanoate
• 英文别名: 8-Oxo-8-p-tolyl-octanoic acid methyl ester；Methyl 8-(4-methylphenyl)-8-oxooctanoate
• CAS: 91202-40-3
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: JZGLCWWJQVOARP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 8-oxo-8-(p-tolyl)octanoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 8-(4-Bromomethyl-phenyl)-8-oxo-octanoic acid methyl ester
  参考文献：
  名称：

  Self-Assembly of Styrylthiophene Amphiphiles in Aqueous Dispersions and Interfacial Films:  Aggregate Structure, Assembly Properties, Photochemistry, and Photophysics

  摘要：

  Fatty acids and phosphatidyl choline derivatives incorporating the photoreactive trans-styrylthiophene chromophore have been prepared and studied in Langmuir-Blodgett films and aqueous dispersions, respectively. Both absorption and fluorescence spectra in the assemblies show prominent shifts indicative of aggregation similar to that observed with similar trans-stilbene and ti-ans-azobenzene derivatives previously investigated. Studies of aqueous dispersions of the pure styrylthiophene phospholipids indicate the formation of structures much larger than the typical small unilamellar bilayer vesicles formed from saturated phospholipids of comparable chain length. Studies of the disaggregation process for two of the phospholipids give aggregation numbers of approximately 2 and 6, corresponding to 4 and 12 styrylthiophene units per aggregate. The stability of these aggregates is very similar to those of corresponding stilbene aggregates, and on the basis of spectral similarities it seems reasonable to propose a "pinwheel" fraction of a glide or herringbone structure as the "unit aggregate" and predominate species present in the aqueous dispersions. However, the chief photoreaction observed for the aqueous dispersions of the phospholipids is dimerization to form the syn head-to-head dimer, consistent with topologically controlled reaction from a translation structure in which nearest-neighbor chromophores are aligned parallel. Simulations suggest that while a translation layer structure may be of lowest energy, glide layer structures that show good agreement between measured and predicted properties are also energetically accessible. A possible explanation for the observed reactivity and photophysics is that within the aqueous dispersions there may be equilibration between "glide" and "translation" structures. When mixtures of the styrylthiophene phospholipids and saturated phospholipids are codispersed, bilayer vesicles are formed that are capable of entrapping reagents such as carboxyfluorescein. irradiation of the aggregated trans-styrylthiophene in these vesicles leads to release of the entrapped carboxyfluorescein concurrent with photodimerization of the styrylthiophene. The pattern of reagent release is similar to that observed upon photoisomerization of the corresponding azobenzene aggregates and suggests a "catastrophic" destruction of the vesicles.

  DOI：

  10.1021/jp973421k
• 作为产物：
  描述：

  环辛酮 在 硫酸 、 2-甲基苯磺酸 、 臭氧 、 magnesium 作用下， 反应 3.33h， 生成 methyl 8-oxo-8-(p-tolyl)octanoate
  参考文献：
  名称：

  有组织的组件中的光化学反应。37. 表面活性剂反式二苯乙烯的光化学和光物理在空气-水界面支撑的多层和薄膜中

  摘要：

  Synthese etude de Dersioactifs du trans-stilbene, qui forme des coches monomoleculaires a l'interface air-eau, transportees a la surface du Quartz pour before des coches multimoleculaires。光异构化与荧光的练习曲

  DOI：

  10.1021/ja00331a041

文献信息

• Chemoselective addition of grignard reagents to alkoxycarbonylalkyl-N-imidazolium-N-methyl amides: Synthesis of 4-oxo and homologous esters
  作者：María A. de las Heras、Juan J. Vaquero、JoséL. García-Navio、Julio Alvarez-Builla

  DOI：10.1016/s0040-4039(97)00159-7

  日期：1997.3

  A method for the synthesis of 4-oxo and homologous esters is achieved by metalation of alkoxycarbonylalkyl-N-imidazolium-N-methyl amides with 1equiv of LDA followed by highly chemoselective addition of 1 equiv of a Grignard reagent.

  通过用1当量的LDA金属化烷氧基羰基烷基-N-咪唑鎓-N-甲基酰胺，然后高度化学选择性地加入1当量的格氏试剂，可以实现合成4-氧代和同源酯的方法。
• Nickel-catalyzed reductive coupling of arylcarboxylic acid 2-pyridyl esters with alkyl methanesulfonates: access to alkyl aryl ketones
  作者：Hang Yu、Zhong-Xia Wang

  DOI：10.1039/d3ob00293d

  日期：——

  Alkyl aryl ketones were synthesized via a nickel-catalyzed reductive coupling reaction of arylcarboxylic acid (2-pyridyl)esters with primary and secondary alkyl methanesulfonates under mild reaction conditions. This method suits a wide range of substrates and shows good compatibility with functional groups.

  在温和的反应条件下，通过芳基羧酸（2-吡啶基）酯与甲磺酸伯和仲烷基酯的镍催化还原偶联反应合成烷基芳基酮。该方法适用于广泛的底物，并显示出与官能团的良好相容性。