4-(1-hydroxy-1,3-diphenylprop-2-ynyl)benzonitrile | 1192167-42-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-(1-hydroxy-1,3-diphenylprop-2-ynyl)benzonitrile
• CAS: 1192167-42-2
• 化学式: C₂₂H₁₅NO
• 分子量: 309.367
• InChiKey: PBIUYEXIDVEVKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(1-hydroxy-1,3-diphenylprop-2-ynyl)benzonitrile 、 硫代乙酰胺 在 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 23.0h， 以98%的产率得到4-((2-methyl-5-phenylthiazol-4-yl)methyl)benzonitrile
  参考文献：
  名称：

  Brønsted Acid Catalyzed Cyclization of Propargylic Alcohols with Thioamides. Facile Synthesis of Di- and Trisubstituted Thiazoles

  摘要：

  A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH center dot H2O-catalyzed cyclization of trisubstituted propargylic alcohols with thioamides is described. The reaction was accomplished in moderate to excellent product yields under mild conditions that did not require the exclusion of air and moisture and offers an operationally simplistic and convenient route to this synthetically useful aromatic heterocycle.

  DOI：

  10.1021/jo101292r
• 作为产物：
  描述：

  苯乙炔 、 4-氰基苯甲酮 在 lithium diisopropyl amide 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 4-(1-hydroxy-1,3-diphenylprop-2-ynyl)benzonitrile
  参考文献：
  名称：

  f化III（III）催化串联Friedel-Crafts炔丙醇与苯酚的烷基化/氢化芳基化为方便地制得吲哚的途径

  摘要：

  描述了一种通过三氟甲磺酸（（III）催化串联Friedel-Crafts炔丙醇与苯酚的烷基化/氢芳基化反应有效地制备茚基的方法。该反应在温和条件下以中等至极好的收率和区域选择性完成，并为生物活性茚及其衍生物提供了简单直接的一步合成途径。

  DOI：

  10.1021/ol901981s

文献信息

• Ytterbium(III) Triflate Catalyzed Tandem Friedel−Crafts Alkylation/Hydroarylation of Propargylic Alcohols with Phenols as an Expedient Route to Indenols
  作者：Xiaoxiang Zhang、Wan Teng Teo、Philip Wai Hong Chan

  DOI：10.1021/ol901981s

  日期：2009.11.5

  A method to prepare indenols efficiently by ytterbium(III) triflate catalyzed tandem Friedel−Crafts alkylation/hydroarylation of propargylic alcohols with phenols is described. The reaction was accomplished in moderate to excellent yields and regioselectivity under mild conditions and offers a straightforward and convenient one step synthetic route to bioactive indenols and its derivatives.

  描述了一种通过三氟甲磺酸（（III）催化串联Friedel-Crafts炔丙醇与苯酚的烷基化/氢芳基化反应有效地制备茚基的方法。该反应在温和条件下以中等至极好的收率和区域选择性完成，并为生物活性茚及其衍生物提供了简单直接的一步合成途径。
• Brønsted Acid Catalyzed Cyclization of Propargylic Alcohols with Thioamides. Facile Synthesis of Di- and Trisubstituted Thiazoles
  作者：Xiaoxiang Zhang、Wan Teng Teo、Sally、Philip Wai Hong Chan

  DOI：10.1021/jo101292r

  日期：2010.9.17

  A general and efficient method to prepare 2,4-di- and trisubstituted thiazoles via p-TsOH center dot H2O-catalyzed cyclization of trisubstituted propargylic alcohols with thioamides is described. The reaction was accomplished in moderate to excellent product yields under mild conditions that did not require the exclusion of air and moisture and offers an operationally simplistic and convenient route to this synthetically useful aromatic heterocycle.