1-环己基-3-苯氧基-2-丙炔-1-醇 | 1023972-55-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-环己基-3-苯氧基-2-丙炔-1-醇
• 英文名称: 1-cyclohexyl-3-phenoxyprop-2-yn-1-ol
• 英文别名: 1-cyclohexyl-3-phenoxy-2-propyn-1-ol；1-Cyclohexyl-3-phenoxyprop-2-yn-1-ol
• CAS: 1023972-55-5
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: LWBGVWYCDRAUBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-环己基-3-苯氧基-2-丙炔-1-醇 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以71%的产率得到(Z)-phenyl 3-cyclohexyl-2-iodoacrylate
  参考文献：
  名称：

  Iodo Meyer–Schuster Rearrangement of 3-Alkoxy-2-yn-1-ols for β-Mono (Exclusively Z-Selective)-/Disubstituted α-Iodo-α,β-Unsaturated Esters

  摘要：

  We herein present the iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols for α-iodo-α,β-unsaturated esters using iodine or NIS in dichloromethane at ambient temperature. Substrates prepared from both aldehydes and ketones are found to be equally good feedstock for the reaction to produce β-mono- and -disubstituted products. Irrespective of the substitution, substrates prepared from aldehydes gave Z-isomers exclusively.

  DOI：

  10.1021/ol502224s
• 作为产物：
  描述：

  苯酚 在 正丁基锂 、 sodium hydroxide 作用下， 以 乙醚 、 正己烷 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 1-环己基-3-苯氧基-2-丙炔-1-醇
  参考文献：
  名称：

  Iodo Meyer–Schuster Rearrangement of 3-Alkoxy-2-yn-1-ols for β-Mono (Exclusively Z-Selective)-/Disubstituted α-Iodo-α,β-Unsaturated Esters

  摘要：

  We herein present the iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols for α-iodo-α,β-unsaturated esters using iodine or NIS in dichloromethane at ambient temperature. Substrates prepared from both aldehydes and ketones are found to be equally good feedstock for the reaction to produce β-mono- and -disubstituted products. Irrespective of the substitution, substrates prepared from aldehydes gave Z-isomers exclusively.

  DOI：

  10.1021/ol502224s

文献信息

• Mo−Au Combo Catalysis for Rapid 1,3-Rearrangement of Propargyl Alcohols into α,β-Unsaturated Carbonyl Compounds
  作者：Masahiro Egi、Yoshiko Yamaguchi、Noboru Fujiwara、Shuji Akai

  DOI：10.1021/ol800596c

  日期：2008.5.1

  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.
• Iodo Meyer–Schuster Rearrangement of 3-Alkoxy-2-yn-1-ols for β-Mono (Exclusively Z-Selective)-/Disubstituted α-Iodo-α,β-Unsaturated Esters
  作者：Surendra Puri、Nuligonda Thirupathi、Maddi Sridhar Reddy

  DOI：10.1021/ol502224s

  日期：2014.10.17

  We herein present the iodo Meyer-Schuster rearrangement of 3-alkoxypropargyl alcohols for α-iodo-α,β-unsaturated esters using iodine or NIS in dichloromethane at ambient temperature. Substrates prepared from both aldehydes and ketones are found to be equally good feedstock for the reaction to produce β-mono- and -disubstituted products. Irrespective of the substitution, substrates prepared from aldehydes gave Z-isomers exclusively.