(S)-5-((R)-2,3-dihydrobenzofuran-3-yl)-4-methylpentan-1-ol | 1571984-88-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-5-((R)-2,3-dihydrobenzofuran-3-yl)-4-methylpentan-1-ol
• CAS: 1571984-88-7
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: APHBZKXOCKHQNS-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-5-((R)-2,3-dihydrobenzofuran-3-yl)-4-methylpentan-1-ol 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 N-((S)-5-((R)-2,3-dihydrobenzofuran-3-yl)-4-methylpentyl)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
• 作为产物：
  描述：

  9-(2-allyloxyphenyl)-9-borabicyclo[3.3.1]nonane 在 lithium aluminium tetrahydride 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 异丁醇 、 异丙醚 为溶剂， 反应 48.83h， 生成 (S)-5-((R)-2,3-dihydrobenzofuran-3-yl)-4-methylpentan-1-ol
  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