2,2,2-trifluoro-N-[2-(2-phenylethynyl)phenyl]-N-[(E)-3-phenylprop-2-enyl]acetamide | 201813-56-1

• 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: 2,2,2-trifluoro-N-[2-(2-phenylethynyl)phenyl]-N-[(E)-3-phenylprop-2-enyl]acetamide
• CAS: 201813-56-1
• 化学式: C₂₅H₁₈F₃NO
• 分子量: 405.419
• InChiKey: CENJHYLZFCWZHA-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-[2-(2-phenylethynyl)phenyl]-N-[(E)-3-phenylprop-2-enyl]acetamide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以91%的产率得到2-phenyl-3-[(E)-3-phenylprop-2-enyl]-1H-indole
  参考文献：
  名称：

  Palladium-Catalyzed Cyclization of o-Alkynyltrifluoroacetanilides with Allyl Esters. A Regioselective Synthesis of 3-Allylindoles

  摘要：

  The reaction of readily available o-alkynyltrifluoroacetanilides 1 with allyl esters provides a valuable new route to 3-allylindoles 3. Three basic procedures have been developed: a stepwise method based on the isolation of the N-allyl derivative 4 and its subsequent cyclization to 3 (procedure a), a one-pot reaction omitting the isolation of 4 (procedure b), and a procedure which most probably leads to the formation of 3 through a mechanism not involving the intermediacy of 4 (procedure c). In the presence of the electron-rich sterically encumbered ligand tris(2,4,6-trimethoxyphenyl)phosphine (ttmpp) the reaction exhibits remarkable regioselectivity and almost exclusive formation of 3-allylindoles with the indolyl moiety bound to the less substituted allyl terminus is usually observed. However, some loss of olefin geometry is observed.

  DOI：

  10.1021/jo971237p
• 作为产物：
  描述：

  2-苯基乙炔基胺 在 tris(dibenzylideneacetone)dipalladium (0) 、 丁基二苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 2,2,2-trifluoro-N-[2-(2-phenylethynyl)phenyl]-N-[(E)-3-phenylprop-2-enyl]acetamide
  参考文献：
  名称：

  Palladium-Catalyzed Cyclization of o-Alkynyltrifluoroacetanilides with Allyl Esters. A Regioselective Synthesis of 3-Allylindoles

  摘要：

  The reaction of readily available o-alkynyltrifluoroacetanilides 1 with allyl esters provides a valuable new route to 3-allylindoles 3. Three basic procedures have been developed: a stepwise method based on the isolation of the N-allyl derivative 4 and its subsequent cyclization to 3 (procedure a), a one-pot reaction omitting the isolation of 4 (procedure b), and a procedure which most probably leads to the formation of 3 through a mechanism not involving the intermediacy of 4 (procedure c). In the presence of the electron-rich sterically encumbered ligand tris(2,4,6-trimethoxyphenyl)phosphine (ttmpp) the reaction exhibits remarkable regioselectivity and almost exclusive formation of 3-allylindoles with the indolyl moiety bound to the less substituted allyl terminus is usually observed. However, some loss of olefin geometry is observed.

  DOI：

  10.1021/jo971237p

文献信息

• Palladium-Catalyzed Cyclization of <i>o</i>-Alkynyltrifluoroacetanilides with Allyl Esters. A Regioselective Synthesis of 3-Allylindoles
  作者：Sandro Cacchi、Giancarlo Fabrizi、Paola Pace

  DOI：10.1021/jo971237p

  日期：1998.2.1

  The reaction of readily available o-alkynyltrifluoroacetanilides 1 with allyl esters provides a valuable new route to 3-allylindoles 3. Three basic procedures have been developed: a stepwise method based on the isolation of the N-allyl derivative 4 and its subsequent cyclization to 3 (procedure a), a one-pot reaction omitting the isolation of 4 (procedure b), and a procedure which most probably leads to the formation of 3 through a mechanism not involving the intermediacy of 4 (procedure c). In the presence of the electron-rich sterically encumbered ligand tris(2,4,6-trimethoxyphenyl)phosphine (ttmpp) the reaction exhibits remarkable regioselectivity and almost exclusive formation of 3-allylindoles with the indolyl moiety bound to the less substituted allyl terminus is usually observed. However, some loss of olefin geometry is observed.