1-(2-苯氧基乙炔基)环己烷-1-醇 | 88297-91-0

• 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-(2-苯氧基乙炔基)环己烷-1-醇
• 英文名称: 1-(phenoxyethynyl)cyclohexanol
• 英文别名: (+/-)-1-Phenoxyaethinyl-cyclohexanol-(1)；1-(Phenoxyethynyl)cyclohexan-1-ol；1-(2-phenoxyethynyl)cyclohexan-1-ol
• CAS: 88297-91-0
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: XPGIURZKWXUKDL-UHFFFAOYSA-N

物化性质

• 熔点：
  43.5-44 °C(Solv: ligroine (8032-32-4))
• 沸点：
  135-138 °C(Press: 0.2 Torr)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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-(2-苯氧基乙炔基)环己烷-1-醇 在 碘 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(cyclohexenylethynyloxy)benzene
  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-(2-苯氧基乙炔基)环己烷-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

• Palladium-Catalyzed Regio- and Stereoselective Cross-Addition of Terminal Alkynes to Ynol Ethers and Synthesis of 1,4-Enyn-3-ones
  作者：Madala Hari Babu、Vikas Dwivedi、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.1002/anie.201411261

  日期：2015.3.16

  Conjugated enynes, enol ethers, and enynones are versatile building blocks that can be elaborated by a wide variety of synthetic transformations. The selective synthesis of such units is a prerequisite for their effective utilization. The synthesis of conjugated 2‐phenoxyenynes through a palladium‐catalyzed cross‐addition of terminal alkynes to phenylethynyl ethers (hydroalkynylation) is now presented

  共轭烯炔，烯醇醚和烯酮是通用的构建基块，可以通过多种合成转化方法进行修饰。这些单元的选择性合成是其有效利用的前提。现在介绍通过末端炔烃与苯乙炔基醚的钯催化交叉加成反应（加氢炔基化反应）合成共轭2-苯氧炔。该反应具有高度的区域，立体和化学选择性，并且对官能团显示出极好的耐受性。该添加物还具有非常温和的反应条件（室温）和廉价的催化体系（无配体且便宜的Pd催化剂）。如此合成的烯丙基醚与烯丙基羟基醚在反应中幸存下来，已证明它们是有价值的1到4炔3到3酮的现成前体。
• Normant,J., Bulletin de la Societe Chimique de France, 1963, p. 1876 - 1887
  作者：Normant,J.

  DOI：——

  日期：——
• Synthesis of some functional derivatives from aroxyacetylenes and aroxypropynes
  作者：G. S. Lyashenko、A. Kh. Filippova、A. I. Borisova、I. D. Kalikhman、N. S. Vyazankin

  DOI：10.1007/bf00954683

  日期：1983.9
• LYASHENKO, G. S.;FILIPPOVA, A. X.;BORISOVA, A. I.;KALIXMAN, I. D.;VYAZANK+, IZV. AN CCCP. CEP. XIM., 1983, N 9, 2153-2156
  作者：LYASHENKO, G. S.、FILIPPOVA, A. X.、BORISOVA, A. I.、KALIXMAN, I. D.、VYAZANK+

  DOI：——

  日期：——
• 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.