(S)-2-[5-(2,3-dihydrobenzofuran-3-yl)pentyl]isoindoline-1,3-dione | 1571984-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S)-2-[5-(2,3-dihydrobenzofuran-3-yl)pentyl]isoindoline-1,3-dione
• 英文别名: 2-[5-[(3S)-2,3-dihydro-1-benzofuran-3-yl]pentyl]isoindole-1,3-dione
• CAS: 1571984-44-5
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: AWWCBZHHWHRJQR-OAHLLOKOSA-N

物化性质

• 沸点：
  474.4±24.0 °C(predicted)
• 密度：
  1.218±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

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)-2-[5-(2,3-dihydrobenzofuran-3-yl)pentyl]isoindoline-1,3-dione
  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.