di(bicyclo[2.2.1]heptan-2-yl)chloroborane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: di(bicyclo[2.2.1]heptan-2-yl)chloroborane
• 英文别名: bis[(1R,2R,4R)-2-bicyclo[2.2.1]heptanyl]-chloroborane
• 化学式: C₁₄H₂₂BCl
• 分子量: 236.593
• InChiKey: FIZRDRGODZJEDW-PRSXHHODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-丁烯酸甲酯 、 di(bicyclo[2.2.1]heptan-2-yl)chloroborane 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成
  参考文献：
  名称：

  Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates

  摘要：

  It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive alpha-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of an aldol reaction in the presence of a phosphine-borane adduct is also reported.

  DOI：

  10.1021/ol400381q
• 作为产物：
  描述：

  norbornene 在 chloroborane methyl sulfide complex 作用下， 以 乙醚 为溶剂， 反应 4.08h， 以91%的产率得到di(bicyclo[2.2.1]heptan-2-yl)chloroborane
  参考文献：
  名称：

  Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates

  摘要：

  It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive alpha-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of an aldol reaction in the presence of a phosphine-borane adduct is also reported.

  DOI：

  10.1021/ol400381q

文献信息

• Total Regio- and Diastereocontrol in the Aldol Reactions of Dienolborinates
  作者：P. Veeraraghavan Ramachandran、Daniel Nicponski、Bomi Kim

  DOI：10.1021/ol400381q

  日期：2013.3.15

  It is reported that appropriate dienolborinates can provide access to both diastereomers of 2-(hydroxymethyl)but-3-enoates through exclusive alpha-regiocontrol in a non-vinylogous pathway. Contrary to previous reports in which dialkylchloroboranes failed to enolize propanoates, acidity-enhanced but-3-enoates readily undergo enolization, offering unprecedented control over the formation of these valuable synthons. The first example of an aldol reaction in the presence of a phosphine-borane adduct is also reported.