(S)-5-(2,3-dihydrobenzofuran-3-yl)-4-(R)-methyl-N,N-diphenylpentanamide | 1571984-78-5

• 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: (S)-5-(2,3-dihydrobenzofuran-3-yl)-4-(R)-methyl-N,N-diphenylpentanamide
• 英文别名: (4R)-5-[(3S)-2,3-dihydro-1-benzofuran-3-yl]-4-methyl-N,N-diphenylpentanamide
• CAS: 1571984-78-5
• 化学式: C₂₆H₂₇NO₂
• 分子量: 385.506
• InChiKey: JZJMHYXOKWXOIE-NHCUHLMSSA-N

物化性质

• 沸点：
  575.3±29.0 °C(predicted)
• 密度：
  1.135±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-2-(2-丙烯-1-基氧基)-苯 在 potassium tert-butylate 、 碘 、 magnesium 作用下， 以 四氢呋喃 、 异丁醇 、 异丙醚 为溶剂， 反应 37.35h， 生成 (S)-5-(2,3-dihydrobenzofuran-3-yl)-4-(R)-methyl-N,N-diphenylpentanamide 、 (R,R)-5-(2,3-dihydrobenzofuran-3-yl)-4-methyl-N,N-diphenylpentanamide 、 (R,R)-5-(2,3-dihydrobenzofuran-3-yl)-4-methyl-N,N-diphenylpentanamide
  参考文献：
  名称：

  Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles

  摘要：

  As part of our ongoing effort to expand the scope of cross-coupling reactions of alkyl electrophiles, we have pursued a strategy wherein the nucleophilic coupling partner includes a pendant olefin; after transmetalation by such a substrate, if beta-migratory insertion proceeds faster than direct cross-coupling, an additional carbon carbon bond and stereocenter can be formed. With the aid of a nickel/diamine catalyst (both components are commercially available), we have established the viability of this approach for the catalytic asymmetric synthesis of 2,3-dihydrobenzofurans and indanes. Furthermore, we have applied this new method to the construction of the dihydrobenzofuran core of fasiglifam, as well as to a cross-coupling with a racemic alkyl electrophile; in the latter process, the chiral catalyst controls two stereocenters, one that is newly generated in a beta-migratory insertion and one that begins as a mixture of enantiomers.

  DOI：

  10.1021/ja500706v

文献信息

• Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles
  作者：Huan Cong、Gregory C. Fu

  DOI：10.1021/ja500706v

  日期：2014.3.12

  As part of our ongoing effort to expand the scope of cross-coupling reactions of alkyl electrophiles, we have pursued a strategy wherein the nucleophilic coupling partner includes a pendant olefin; after transmetalation by such a substrate, if beta-migratory insertion proceeds faster than direct cross-coupling, an additional carbon carbon bond and stereocenter can be formed. With the aid of a nickel/diamine catalyst (both components are commercially available), we have established the viability of this approach for the catalytic asymmetric synthesis of 2,3-dihydrobenzofurans and indanes. Furthermore, we have applied this new method to the construction of the dihydrobenzofuran core of fasiglifam, as well as to a cross-coupling with a racemic alkyl electrophile; in the latter process, the chiral catalyst controls two stereocenters, one that is newly generated in a beta-migratory insertion and one that begins as a mixture of enantiomers.