1-(4-chlorophenyl)-1-cyclopropyl-3-phenylprop-2-yn-1-ol | 1109231-84-6

• 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: 1-(4-chlorophenyl)-1-cyclopropyl-3-phenylprop-2-yn-1-ol
• CAS: 1109231-84-6
• 化学式: C₁₈H₁₅ClO
• 分子量: 282.769
• InChiKey: JGKBBSRKALRZAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-1-cyclopropyl-3-phenylprop-2-yn-1-ol 、 对甲苯磺酰胺 在 ytterbium(III) triflate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以67%的产率得到(Z)-N-(4-(4-chlorophenyl)-6-phenylhex-3-en-5-ynyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Ytterbium(III) Triflate-Catalyzed Amination of 1-Cyclopropylprop-2-yn-1-ols as an Expedient Route to Conjugated Enynes

  摘要：

  Ytterbium(III) triflate-catalyzed ring opening of substituted 1-cyclopropyl-2-propyn-1-ols with sulfonamides as an efficient synthetic route to conjugated enynes is described herein. The reaction was operationally straightforward and accomplished in moderate to good yields and recgioselective manner in all except one case under mild conditions.

  DOI：

  10.1021/jo8024626
• 作为产物：
  描述：

  4-氯苯基环丙基甲酮 、 苯乙炔 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 1-(4-chlorophenyl)-1-cyclopropyl-3-phenylprop-2-yn-1-ol
  参考文献：
  名称：

  Ytterbium(III) Triflate-Catalyzed Amination of 1-Cyclopropylprop-2-yn-1-ols as an Expedient Route to Conjugated Enynes

  摘要：

  Ytterbium(III) triflate-catalyzed ring opening of substituted 1-cyclopropyl-2-propyn-1-ols with sulfonamides as an efficient synthetic route to conjugated enynes is described herein. The reaction was operationally straightforward and accomplished in moderate to good yields and recgioselective manner in all except one case under mild conditions.

  DOI：

  10.1021/jo8024626

文献信息

• Brønsted acid−catalyzed synthesis of tetrasubstituted allenes and polysubstituted 2H-chromenes from tertiary propargylic alcohols
  作者：Natalia Cabrera-Lobera、Noelia Velasco、Roberto Sanz、Manuel A. Fernández-Rodríguez

  DOI：10.1016/j.tet.2019.05.023

  日期：2019.8

  A practical and environmentally benign Brønsted acid−catalyzed protocol for the preparation of all-carbon tetrasubstituted allenes, consisting in the direct SNˈ addition of tri- or dimethoxy arenes or allyltrimethylsilane to tertiary propargylic alcohols, has been developed. In addition, a straightforward synthesis of densely substituted 2H-chromenes by metal-free tandem allenylation/heterocyclization

  已经开发了一种实用且对环境无害的布朗斯台德酸催化方案，用于制备全碳四取代的烯，其中包括将三或二甲氧基芳烃或烯丙基三甲基硅烷直接S N加到叔炔丙醇中。另外，提出了通过甲氧基苯酚和叔炔醇的无金属串联烯丙基化/杂环化反应直接合成密集取代的2 H-色烯。
• 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.