N-[(E)-3-(4-Acetyl-phenyl)-allyl]-2,2,2-trifluoro-N-(2-phenylethynyl-phenyl)-acetamide | 201813-70-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(E)-3-(4-Acetyl-phenyl)-allyl]-2,2,2-trifluoro-N-(2-phenylethynyl-phenyl)-acetamide
• 英文别名: N-[(E)-3-(4-acetylphenyl)prop-2-enyl]-2,2,2-trifluoro-N-[2-(2-phenylethynyl)phenyl]acetamide
• CAS: 201813-70-9
• 化学式: C₂₇H₂₀F₃NO₂
• 分子量: 447.457
• InChiKey: OFRLEPOTRLUWDN-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(E)-3-(4-Acetyl-phenyl)-allyl]-2,2,2-trifluoro-N-(2-phenylethynyl-phenyl)-acetamide 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以77%的产率得到1-{4-[(E)-3-(2-Phenyl-1H-indol-3-yl)-propenyl]-phenyl}-ethanone
  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 palladium diacetate 、 tris(dibenzylideneacetone)dipalladium (0) 、 potassium acetate 、 potassium carbonate 、 丁基二苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 N-[(E)-3-(4-Acetyl-phenyl)-allyl]-2,2,2-trifluoro-N-(2-phenylethynyl-phenyl)-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.