9-[2-(3-methyl-3-buten-1-yl)phenyl]-9-borabicyclo[3.3.1]nonane | 1571984-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 9-[2-(3-methyl-3-buten-1-yl)phenyl]-9-borabicyclo[3.3.1]nonane
• CAS: 1571984-67-2
• 化学式: C₁₉H₂₇B
• 分子量: 266.234
• InChiKey: DKCNHCWPINESDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1-碘-3-苯基丙烷 、 9-[2-(3-methyl-3-buten-1-yl)phenyl]-9-borabicyclo[3.3.1]nonane 在 potassium tert-butylate 、 乙二醇二甲醚溴化镍 、 (1R,2R)-(+)-N,N-二甲基-1,2-二苯基-1,2-二乙胺 作用下， 以 四氢呋喃 、 异丁醇 、 异丙醚 为溶剂， 反应 36.83h， 以57%的产率得到
  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：

  4-(2-溴苯基)-2-甲基-1-丁烯 、 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-(3-methyl-3-buten-1-yl)phenyl]-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