phenyl 3-cyclohexylacrylate | 1023972-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl 3-cyclohexylacrylate
• CAS: 1023972-59-9
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: ZXJJFQVGWVSKMT-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-己炔 、 phenyl 3-cyclohexylacrylate 在 bis(1,5-cyclooctadiene)nickel (0) 、 锌 、 三环己基膦 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 以49%的产率得到4-cyclohexyl-2,3-diethylcyclopent-2-enone
  参考文献：
  名称：

  Nickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique Cycloaddition of α,β-Unsaturated Phenyl Esters with Alkynes

  摘要：

  Oxygen-containing organic compounds, such as ethers, carboxylates, and carbamates, have recently received increasing attention because of their newly discovered applications as electrophiles in cross-coupling reactions via transition metal-catalyzed C-O bond activation. However, no cycloaddition reaction involving their C-O bond activation has been demonstrated thus far. The present study developed a Ni(O)-catalyzed unique [3+2] cycloaddition reaction of alpha,beta-unsaturated phenyl esters with alkynes in (PrOH)-Pr-i to yield cydopentenone derivatives.

  DOI：

  10.1021/ja2059999
• 作为产物：
  描述：

  1-环己基-3-苯氧基-2-丙炔-1-醇 在 bis(acetylacetonato)dioxidomolybdenum(VI) 、 [Au(Cl)PPh₃] 、 silver trifluoromethanesulfonate 作用下， 以 丙酮 为溶剂， 反应 0.25h， 生成 phenyl 3-cyclohexylacrylate 、 phenyl 3-cyclohexylacrylate
  参考文献：
  名称：

  Mo−Au Combo Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols into α,β-Unsaturated Carbonyl Compounds

  摘要：

  The combination of Mo and cationic Au catalysts dramatically accelerated the rearrangement of diverse propargyl alcohols, which includes a short reaction time, mild conditions, and high product yields. A practical application to the highly challenging primary propargyl alcohols and the N-alkynyl amides is achieved.

  DOI：

  10.1021/ol800596c

文献信息

• Palladium-Catalyzed Hydroesterification of Alkynes Employing Aryl Formates without the Use of External Carbon Monoxide
  作者：Yuko Katafuchi、Tetsuaki Fujihara、Tomohiro Iwai、Jun Terao、Yasushi Tsuji

  DOI：10.1002/adsc.201000750

  日期：2011.2.11

  highly efficient hydroesterification of alkynes employing aryl formates has been developed without the use of external carbon monoxide and at ambient pressure. The reaction in the presence of a palladium-xantphos catalyst system selectively affords α,β-unsaturated esters in good to high yields. Use of an aryl formate is crucial and alkyl formates did not react at all. The hydroesterification of norbornene

  已经开发了在不使用外部一氧化碳的情况下并且在环境压力下使用芳基甲酸酯的炔烃的高效加氢酯化。在钯-黄磷催化剂体系存在下的反应以良好至高收率选择性地提供α，β-不饱和酯。甲酸芳基酯的使用至关重要，烷基甲酸酯根本不反应。降冰片烯和末端烯烃的加氢酯化也容易在相似的反应条件下进行。机理研究表明，加氢酯化过程中发生了芳基甲酸酯向一氧化碳和苯酚衍生物的转化。Xantphos作为芳基甲酸酯的转化和加氢酯化反应的配体都是非常有效的。