(+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one | 19019-49-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one
• 英文别名: 6-acetoxy-3,5,5-trimethyl-2-cyclohexenone；6-acetyloxy-3,5,5-trimethylcyclohex-2-enone；6-acetylisophorone；6-Acetoxy-isophoron；3,5,5-Trimethyl-6-acetoxy-2-cyclohexen-1-on；6-Acetoxy-3,5,5-trimethyl-2-cyclohexen-1-on；6-Acetoxy-3,5,5-trimethyl-2-cyclohexenon；2-Acetoxy-isophoron；4,6,6-Trimethyl-2-oxocyclohex-3-en-1-yl acetate；(4,6,6-trimethyl-2-oxocyclohex-3-en-1-yl) acetate
• CAS: 19019-49-9
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: PIJJANMPLRSMQN-UHFFFAOYSA-N

物化性质

• 熔点：
  77-77.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  267.7±40.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one 在 2 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以74%的产率得到异佛尔酮
  参考文献：
  名称：

  用钒(II)-THF配合物去除丙烯酰基及其衍生物的α-羟基

  摘要：

  通过用由 VCl3(THF)3 和锌原位制备的 [V2Cl3(THF)6]2[Zn2Cl6] 络合物处理，α-羟基酮（酰基）及其乙酸酯或甲磺酸酯衍生物以良好的产率还原为相应的酮。

  DOI：

  10.1246/cl.1992.1895
• 作为产物：
  描述：

  异佛尔酮 在 吡啶 、 氢氧化钾 、 碘苯二乙酸 作用下， 反应 0.5h， 生成 (+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one
  参考文献：
  名称：

  Tamura, Yasumitsu; Yakura, Takayuki; Terashi, Hiroaki, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 2, p. 570 - 577

  摘要：

  DOI：

文献信息

• Potassium permanganate/carboxylic acid/organic solvent: a powerful reagent for enone oxidation and aryl coupling reactions
  作者：Ayhan S. Demir、Hamide Findik

  DOI：10.1016/j.tet.2008.05.004

  日期：2008.6

  with potassium permanganate and acetic acid, in which acetoxylation products were obtained in 74–96% yields. The same reaction was carried out with carboxylic acids other than acetic acid, which furnished corresponding acyloxy ketones with the same regioselectivity. For the first time, formyloxylation products were synthesized in a 61–85% yield by using formic acid. The potassium permanganate and acetic

  用高锰酸钾和乙酸进行烯酮的α'-乙酰氧基化和芳族酮的α-乙酰氧基化，得到乙酰氧基化产物的产率为74-96％。用乙酸以外的羧酸进行相同的反应，这提供了具有相同区域选择性的相应的酰氧基酮。首次使用甲酸以61-85％的产率合成了甲酰氧基化产物。高锰酸钾和乙酸法也用于芳基偶联反应。苯中的芳基硼酸和芳基肼与高锰酸钾和乙酸的反应反过来提供了85-96％的收率。我们已经证明高锰酸钾/羧酸/有机溶剂的行为像乙酸锰（III）。
• Reactions involving electron transfer. II. Reductions of enones with alkali metal solutions
  作者：Herbert O. House、Roger W. Giese、Karlheinz Kronberger、Jean P. Kaplan、Joseph F. Simeone

  DOI：10.1021/ja00712a033

  日期：1970.5
• Acyloxylation of Cyclic Enones: Synthesis of Densely Oxygenated Guaianolides
  作者：Rubén Marín-Barrios、Ana Leticia García-Cabeza、F. Javier Moreno-Dorado、Francisco M. Guerra、Guillermo M. Massanet

  DOI：10.1021/jo500915r

  日期：2014.7.18

  The alpha'-acyloxylation of cyclic enones with linear carboxylic acids is described. The reaction is promoted by KMnO4 in the presence of a carboxylic acid and its corresponding carboxylic anhydride. The optimization of the reaction has been carried out using the statistical methodology known as design of experiments. The optimized reaction conditions have been evaluated in terms of substrate scope and compatibility with different functional groups. The methodology has been applied to the synthesis of densely oxygenated guaianes and guaianolides.
• Cleavage of unsaturated .alpha.-ketols to .omega.-oxo-.alpha.,.beta.-unsaturated acids
  作者：Rey Floresca、Masaaki Kurihara、David S. Watt、Ayhan Demir

  DOI：10.1021/jo00060a040

  日期：1993.4

  Sodium periodate is a better reagent than sodium bismuthate, manganese dioxide, or lead tetraacetate for the cleavage of unsaturated alpha-ketols and affords omega-oxo-alpha,beta-unsaturated acids in good yield. The combination of this cleavage reaction and a rhodium(I)-mediated decarbonylation of omega-oxo-alpha,beta-unsaturated esters derived from polycyclic systems provided an enantioselective synthesis of cyclic systems bearing contiguous quaternary centers where one of the centers possessed gem-dimethyl groups.
• m-Chloroperbenzoic acid oxidation of 2-trimethylsilyloxy-1,3-dienes. Synthesis of .alpha.-hydroxy and .alpha.-acetoxy enones
  作者：G. M. Rubottom、J. M. Gruber

  DOI：10.1021/jo00402a030

  日期：1978.4