2-[(1S)-1-cyclopropylethyl]-1,3,2-dioxaborinane | 1344116-04-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 2-[(1S)-1-cyclopropylethyl]-1,3,2-dioxaborinane
• CAS: 1344116-04-6
• 化学式: C₈H₁₅BO₂
• 分子量: 154.017
• InChiKey: JBRSYBCLYOLSKU-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1S)-1-cyclopropylethyl]-1,3,2-dioxaborinane 在 草酰氯 、 二氯苯酚溴酯 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.83h， 生成
  参考文献：
  名称：

  Homoallylboration and Homocrotylboration of Aldehydes

  摘要：

  A simple method for addition of homoallylic fragments to aldehydes is described. Cydopropanated allylboration reagents react with aldehydes in the presence of PhBCl2 to give high yields of bishomoallyl alcohols. Cyclopropanated cis- and trans-crotyl reagents afford the corresponding 1,3-anti- and 1,3-syn-methyl-substituted "homocrotylated" alcohols with high selectivity, consistent with a Zimmerman-Traxler transition state. Accordingly, the optically active alpha-substituted reactant affords the E-substituted product in 97:3 er.

  DOI：

  10.1021/ja2048682
• 作为产物：
  描述：

  在 CsFH₂ 、 氢氟酸 、 silica gel 作用下， 以 乙醚 、 水 为溶剂， 反应 1.0h， 生成 2-[(1S)-1-cyclopropylethyl]-1,3,2-dioxaborinane
  参考文献：
  名称：

  Homoallylboration and Homocrotylboration of Aldehydes

  摘要：

  A simple method for addition of homoallylic fragments to aldehydes is described. Cydopropanated allylboration reagents react with aldehydes in the presence of PhBCl2 to give high yields of bishomoallyl alcohols. Cyclopropanated cis- and trans-crotyl reagents afford the corresponding 1,3-anti- and 1,3-syn-methyl-substituted "homocrotylated" alcohols with high selectivity, consistent with a Zimmerman-Traxler transition state. Accordingly, the optically active alpha-substituted reactant affords the E-substituted product in 97:3 er.

  DOI：

  10.1021/ja2048682

文献信息

• Homoallylboration and Homocrotylboration of Aldehydes
  作者：Wenbo Pei、Isaac J. Krauss

  DOI：10.1021/ja2048682

  日期：2011.11.23

  A simple method for addition of homoallylic fragments to aldehydes is described. Cydopropanated allylboration reagents react with aldehydes in the presence of PhBCl2 to give high yields of bishomoallyl alcohols. Cyclopropanated cis- and trans-crotyl reagents afford the corresponding 1,3-anti- and 1,3-syn-methyl-substituted "homocrotylated" alcohols with high selectivity, consistent with a Zimmerman-Traxler transition state. Accordingly, the optically active alpha-substituted reactant affords the E-substituted product in 97:3 er.