syn-2-(1-Hydroxy-2-hexenyl)cyclohexanone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: syn-2-(1-Hydroxy-2-hexenyl)cyclohexanone
• 英文别名: anti-2-(1-Hydroxy-2-hexenyl)cyclohexanone；2-[(E)-1-hydroxyhex-2-enyl]cyclohexan-1-one
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: OGEWLJXTIVAWLP-XBXARRHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-已烯醛 、 1-环己烯氧基三甲基硅烷 在 ytterbium(III) triflate 作用下， 以 水 为溶剂， 反应 20.0h， 以77%的产率得到syn-2-(1-Hydroxy-2-hexenyl)cyclohexanone
  参考文献：
  名称：

  水性介质中甲硅烷基烯醇醚与醛的醛醇缩合反应

  摘要：

  通过使用镧系三氟甲烷磺酸盐作为催化剂，在水性介质中成功地进行了甲硅烷基烯醇醚与醛的醛醇缩合反应。水溶性醛是适用的，并且该催化剂可以回收并在该反应中重复使用。

  DOI：

  10.1016/s0040-4039(00)91691-5

文献信息

• The Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media
  作者：Shū Kobayashi、Iwao Hachiya

  DOI：10.1016/s0040-4039(00)91691-5

  日期：1992.3

  The aldol reaction of silyl enol ethers with aldehydes is successfully carried out in aqueous media by using a lanthanide trifluoromethanesulfonate as a catalyst. Water soluble aldehydes are applicable and the catalyst can be recovered and reused in this reaction.

  通过使用镧系三氟甲烷磺酸盐作为催化剂，在水性介质中成功地进行了甲硅烷基烯醇醚与醛的醛醇缩合反应。水溶性醛是适用的，并且该催化剂可以回收并在该反应中重复使用。
• Trimethylsilyl trifltate catalyzed aldol-type reaction of enol silyl ethers and acetals or related compounds
  作者：Shizuaki Murata、Masaaki Suzuki、Ryoji Noyori

  DOI：10.1016/s0040-4020(01)86671-0

  日期：1988.1

  condensation of enol trimethylsllyl ethers with acetals, orthoformate, or 2-acetoxytetrahydrofuran or -pyrans to give the corresponding β-alkoxy carbonyl compounds. Reaction of enol silyl ethers and carboxonium triflate ion-pair intermediates occurs via acyclic transition states and exhibits moderate to high erythro selectivity independent of the geometry (E/Z) of the enol silyl ethers.

  加入或不加入受阻叔胺的三氟甲磺酸三甲基甲硅烷基酯催化烯醇三甲基甲硅烷基醚与缩醛，原甲酸酯或2-乙酰氧基四氢呋喃或-吡喃的定向缩合，得到相应的β-烷氧基羰基化合物。烯醇甲硅烷基醚与三氟甲磺酸钾离子对中间体的反应通过无环过渡态发生，并且表现出中等至高的赤型选择性，而与烯醇甲硅烷基醚的几何形状（E / Z）无关。
• Lanthanide Triflates as Water-Tolerant Lewis Acids. Activation of Commercial Formaldehyde Solution and Use in the Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous Media
  作者：Shu Kobayashi、Iwao Hachiya

  DOI：10.1021/jo00092a017

  日期：1994.7

  Lanthanide trifluoromethanesulfonates (triflates), especially ytterbium triflate (Yb(OTf)(3)), were found to be stable Lewis acids in water. In the presence of a catalytic amount of lanthanide triflate, formaldehyde in water solution (commercial formaldehyde solution) was activated and the hydroxymethylation reaction of silyl enol ethers proceeded smoothly. Lanthanide triflates were also quite effective in the aldol reaction of silyl enol ethers with aldehydes in aqueous media, and water-soluble aldehydes such as acetaldehyde, acrolein, and chloroacetaldehyde could be employed for direct use. Moreover, in all these reactions, lanthanide triflates were quantitatively recovered after the reactions were completed and could be reused.