bis(1-pentyl)isopropoxyborane | 138152-38-2

• 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: bis(1-pentyl)isopropoxyborane
• 英文别名: dipentyl(propan-2-yloxy)borane
• CAS: 138152-38-2
• 化学式: C₁₃H₂₉BO
• 分子量: 212.184
• InChiKey: CKHVCCIFRMFTLD-UHFFFAOYSA-N

物化性质

• 沸点：
  258.3±9.0 °C(Predicted)
• 密度：
  0.780±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  15.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  硼酸三异丙酯 、 正戊基溴化镁 以 乙醚 为溶剂， 以77%的产率得到bis(1-pentyl)isopropoxyborane
  参考文献：
  名称：

  从格氏试剂和精选的三烷氧基硼烷选择性制备硼酸酯

  摘要：

  The reaction of trialkoxyboranes with ethylmagnesium bromide was investigated for the selective alkylation to the symmetrical borinic esters, R2BOR'. Triisopropoxyborane was found to react cleanly with 2 equiv of the Gringnard reagent to form diethylisopropoxyborane at -40-degrees-C. The selectivity of this reaction is largely controlled by the stability of the bromomagnesium diethyldiisopropoxyborate, MgBr[Et2B(O(i)Pr)2]. Triisopropoxyborane was found to be the most selective borane examined, yielding symmetrical borinic esters for primary and aryl derivatives with high selectivities. Secondary alkyl groups showed lower selectivities. This reaction has been developed into a general procedure for preparation of diorganyl-alkoxyboranes from readily available organomagnesium reagents, especially for those containing organic groups which are not accessible via hydroboration.

  DOI：

  10.1021/om00038a024

文献信息

• Selective preparation of borinic esters from Grignard reagents and selected trialkoxyboranes
  作者：Thomas E. Cole、Becky D. Haly

  DOI：10.1021/om00038a024

  日期：1992.2

  The reaction of trialkoxyboranes with ethylmagnesium bromide was investigated for the selective alkylation to the symmetrical borinic esters, R2BOR'. Triisopropoxyborane was found to react cleanly with 2 equiv of the Gringnard reagent to form diethylisopropoxyborane at -40-degrees-C. The selectivity of this reaction is largely controlled by the stability of the bromomagnesium diethyldiisopropoxyborate, MgBr[Et2B(O(i)Pr)2]. Triisopropoxyborane was found to be the most selective borane examined, yielding symmetrical borinic esters for primary and aryl derivatives with high selectivities. Secondary alkyl groups showed lower selectivities. This reaction has been developed into a general procedure for preparation of diorganyl-alkoxyboranes from readily available organomagnesium reagents, especially for those containing organic groups which are not accessible via hydroboration.