1-cyclopropyl-1-(4-fluorophenyl)-3-(pyridin-2-yl)prop-2-yn-1-ol | 1181658-08-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-cyclopropyl-1-(4-fluorophenyl)-3-(pyridin-2-yl)prop-2-yn-1-ol
• 英文别名: 1-Cyclopropyl-1-(4-fluorophenyl)-3-pyridin-2-ylprop-2-yn-1-ol
• CAS: 1181658-08-1
• 化学式: C₁₇H₁₄FNO
• 分子量: 267.303
• InChiKey: YAIYLPCEBVIPAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙醇 、 1-cyclopropyl-1-(4-fluorophenyl)-3-(pyridin-2-yl)prop-2-yn-1-ol 在 三氟甲磺酸 作用下， 以91%的产率得到2-((Z)-6-ethoxy-3-(4-fluorophenyl)hex-3-en-1-ynyl)pyridine
  参考文献：
  名称：

  Highly Efficient Synthesis of Tri- and Tetrasubstituted Conjugated Enynes from Brønsted Acid Catalyzed Alkoxylation of 1-Cyclopropylprop-2-yn-1-ols with Alcohols

  摘要：

  A highly efficient triflic acid catalyzed ring opening of a wide variety of 1-cyclopropyl-2-propyn-1-ols with alcohols as an efficient synthetic route to conjugated enynes is reported herein. The reaction was operationally straight forward and accomplished in good to excellent yields (44-100%,), high product turnovers (up to 10,000), and with complete regioselectivity under mild conditions with a low catalyst loading of 0.01 mol%. The mechanism is suggested to involve protonation of the alcohol substrate by the TfOH catalyst, followed by ionization of the starting material. This causes ring opening, of the cyclopropane moiety and trapping by the alcohol nucleophile to give the conjugated enyne product. The synthetic utility Of the present method was also exemplified by the efficient large-scale Conversion in grain quantities of one example studied in this work to the corresponding conjugated enyne product in excellent yield and turnover number.

  DOI：

  10.1021/jo9008244
• 作为产物：
  描述：

  2-乙炔基吡啶 、 4-氟苯基环丙基甲酮 在 lithium diisopropyl amide 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以72%的产率得到1-cyclopropyl-1-(4-fluorophenyl)-3-(pyridin-2-yl)prop-2-yn-1-ol
  参考文献：
  名称：

  Highly Efficient Synthesis of Tri- and Tetrasubstituted Conjugated Enynes from Brønsted Acid Catalyzed Alkoxylation of 1-Cyclopropylprop-2-yn-1-ols with Alcohols

  摘要：

  A highly efficient triflic acid catalyzed ring opening of a wide variety of 1-cyclopropyl-2-propyn-1-ols with alcohols as an efficient synthetic route to conjugated enynes is reported herein. The reaction was operationally straight forward and accomplished in good to excellent yields (44-100%,), high product turnovers (up to 10,000), and with complete regioselectivity under mild conditions with a low catalyst loading of 0.01 mol%. The mechanism is suggested to involve protonation of the alcohol substrate by the TfOH catalyst, followed by ionization of the starting material. This causes ring opening, of the cyclopropane moiety and trapping by the alcohol nucleophile to give the conjugated enyne product. The synthetic utility Of the present method was also exemplified by the efficient large-scale Conversion in grain quantities of one example studied in this work to the corresponding conjugated enyne product in excellent yield and turnover number.

  DOI：

  10.1021/jo9008244

文献信息

• Highly Efficient Synthesis of Tri- and Tetrasubstituted Conjugated Enynes from Brønsted Acid Catalyzed Alkoxylation of 1-Cyclopropylprop-2-yn-1-ols with Alcohols
  作者：Srinivasa Reddy Mothe、Philip Wai Hong Chan

  DOI：10.1021/jo9008244

  日期：2009.8.21

  A highly efficient triflic acid catalyzed ring opening of a wide variety of 1-cyclopropyl-2-propyn-1-ols with alcohols as an efficient synthetic route to conjugated enynes is reported herein. The reaction was operationally straight forward and accomplished in good to excellent yields (44-100%,), high product turnovers (up to 10,000), and with complete regioselectivity under mild conditions with a low catalyst loading of 0.01 mol%. The mechanism is suggested to involve protonation of the alcohol substrate by the TfOH catalyst, followed by ionization of the starting material. This causes ring opening, of the cyclopropane moiety and trapping by the alcohol nucleophile to give the conjugated enyne product. The synthetic utility Of the present method was also exemplified by the efficient large-scale Conversion in grain quantities of one example studied in this work to the corresponding conjugated enyne product in excellent yield and turnover number.