9-(2-allyloxyphenyl)-9-borabicyclo[3.3.1]nonane | 1571984-25-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 9-(2-allyloxyphenyl)-9-borabicyclo[3.3.1]nonane
• 英文别名: 9-(2-Prop-2-enoxyphenyl)-9-borabicyclo[3.3.1]nonane；9-(2-prop-2-enoxyphenyl)-9-borabicyclo[3.3.1]nonane
• CAS: 1571984-25-2
• 化学式: C₁₇H₂₃BO
• 分子量: 254.18
• InChiKey: WLSVGIUIHQBFKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-(2-allyloxyphenyl)-9-borabicyclo[3.3.1]nonane 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丁醇 、 异丙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.83h， 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：

  1-溴-2-(2-丙烯-1-基氧基)-苯 、 9-borabicyclo[3.3.1]nonane dimer 在 碘 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.52h， 生成 9-(2-allyloxyphenyl)-9-borabicyclo[3.3.1]nonane
  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.