6-氧代-环己-1-烯基乙酸酯 | 5011-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-氧代-环己-1-烯基乙酸酯
• 英文名称: 2-acetoxy-2-cyclohexen-1-one
• 英文别名: 2-acetoxy-2-cyclohexenone；1,2-cyclohexanedione enol acetate；2-acetoxy-cyclohex-2-enone；2-Acetoxy-cyclohex-2-enon；2-acetoxy-cyclohex-2-en-1-one；6-Oxocyclohex-1-EN-1-YL acetate；(6-oxocyclohexen-1-yl) acetate
• CAS: 5011-76-7
• 化学式: C₈H₁₀O₃
• mdl: MFCD09033480
• 分子量: 154.166
• InChiKey: STOYPPHPIKFQEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  6-氧代-环己-1-烯基乙酸酯 在 Pd-BaSO₄ 、 乙醇 作用下， 生成 2-羟基环己酮二聚物
  参考文献：
  名称：

  Rosenmund et al., Chemische Berichte, 1959, vol. 92, p. 494,499

  摘要：

  DOI：
• 作为产物：
  描述：

  在 吡啶 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到6-氧代-环己-1-烯基乙酸酯
  参考文献：
  名称：

  Buckley, Daniel J.; McKervey, M. Anthony, Journal of the Chemical Society. Perkin transactions I, 1985, p. 2193 - 2200

  摘要：

  DOI：

文献信息

• A One-Pot Isomerization−Arylation of 2,3-Epoxycyclohexanone under Controlled Microwave Heating
  作者：Andreas Svennebring、Neeraj Garg、Peter Nilsson、Anders Hallberg、Mats Larhed

  DOI：10.1021/jo0504619

  日期：2005.6.1

  method has been developed for the direct preparation of 3-aryl-1,2-cyclohexanediones from 2,3-epoxycyclohexanone via a microwave-assisted tandem epoxy ketone isomerization−Heck arylation reaction. The preparative microwave-assisted reactions were performed preferentially in 50% aqueous poly(ethylene glycol) utilizing sodium acetate as the base. Within 5−30 min of directed microwave heating, employing less

  已经开发了一种快速的一锅法，可通过微波辅助串联环氧酮异构化-Heck芳基化反应从2,3-环氧环己酮直接制备3-芳基-1,2-环己二酮。制备微波辅助反应优选在乙酸钠为碱的50％聚乙二醇水溶液中进行。在直接微波加热的5-30分钟内，使用少于0.05 mol％的乙酸钯且没有膦配体，在整个环境友好的过程中，分离出高达72％的C3-芳基二酮收率。基于所提出的中间体的化学反应性，提出了一种反应途径，其中乙酸盐碱促进了2，3-环氧环己酮的重排成1，2-环己二酮的活性单烯醇形式。
• Synthesis of 2,3-Dihydrobenzofurans by Mn(OAc)₃-Based Oxidative Cycloaddition of 2-Cyclohexenones with Alkenes. Synthesis of (±)-Conocarpan
  作者：Barry B. Snider、Luning Han、Chaoyu Xie

  DOI：10.1021/jo9708506

  日期：1997.10.1

  Oxidative cycloaddition of a 2-cyclohexenone or alpha-tetralone and an alkene with dried Mn(OAc)(3) in benzene at 80-140 degrees C provides a general route to dihydrobenzofurans 15 and dihydronaphthofurans 17. Although the yields are modest, this one-pot reaction provides simple access to these compounds, which have previously been prepared by multistep routes. Oxidative cycloaddition of 2-cyclohexenones with beta-methylstyrenes provides a new route to benzofuranoid neolignans, which was applied to the synthesis of conocarpan (22). The formation of 2-acetoxyhexanedioic acids 27 and 47 from acetoxylation of 2-cyclohexenones in HOAc, but not in benzene, opens up a new class of Mn(OAc)(3) reactions and explains Watt and Demir's discovery that much higher yields of alpha'-acetoxy enones are obtained in benzene than in HOAc.
• <i>Rhodotorula minuta</i>-mediated bioreduction of 1,2-diketones
  作者：Leandro N. Monsalve、Patricia Cerrutti、Miguel A. Galvagno、Alicia Baldessari

  DOI：10.3109/10242420903515445

  日期：2010.1

  The reduction of cyclic and acyclic 1,2-diketones was investigated by employing whole cells of the yeast Rhodotorula minuta as biocatalyst. The reactions showed a variable degree of regio- and enantioselectivity depending on the nature of the substrate. In the case of cyclic diketones, the reduction afforded a mixture of diastereomeric diols only. The reduction of acyclic diketones allowed production of both the hydroxy ketone and the diol, in a two-step reaction. The first step was highly regio- and stereoselective, affording the hydroxy ketone of (S)-configuration with high enantiomeric excess. After longer reaction times the corresponding (S,S)-diols were obtained in high yield and diastereomeric excess.
• 1,3-Elimination-Rearrangement of 2-Acetoxy-6-bromocyclohexanones
  作者：Frederick G. Bordwell、Keith M. Wellman

  DOI：10.1021/jo01340a001

  日期：1966.2
• Zum Verhalten von Orthocarbonsäureestern gegenüber Trimethylsilylchlorid, -azid und -cyanid
  作者：Friedrich Becsi、Erich Zbiral

  DOI：10.1007/bf00906692

  日期：1979.7