diamyl borane | 105740-22-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: diamyl borane
• 英文别名: diamylborane；Dipentylboran；Dipentylborane；dipentylborane
• CAS: 105740-22-5
• 化学式: C₁₀H₂₃B
• 分子量: 154.104
• InChiKey: ZOYIRSVTXOTVSM-UHFFFAOYSA-N

物化性质

• 沸点：
  204.6±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  11
• 可旋转键数：
  8
• 环数：
  0.0
• 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：

  diamyl borane 、 1-bromohexyne 以80%的产率得到
  参考文献：
  名称：

  ARASE, AKIRA;HOSHI, MASAYUKI;MASUDA, YUZURU, BULL. CHEM. SOC. JAP., 1984, 57, N 1, 209-213

  摘要：

  DOI：
• 作为产物：
  描述：

  戊烯 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 tripentylborane 、 diamyl borane
  参考文献：
  名称：

  Hydroboration. VI. A Convenient Synthesis of the Alkane and Cycloalkane Boronic and Borinic Esters and Acids

  摘要：

  The addition of I-pentene or cyclopentene to a solution of one-half the molar quantity of diborane in tetrahydroftiran solution at 0 degrees results in the formation of 60 to 65% yields of di-n-pentylborane and dicyclopentylborane, readily converted to the corresponding borinic methyl esters by treatment with methanol. Equilibration of the initial reaction mixture with a deficiency of diborane (2 olefin/1 BH3) leads to the preferred formation of di-n-pentylborane in the case of I-pentene, but to the preferred formation of monocyclopentylborane (and tricyclopentylborane) in the case of the cyclic olefin, cyclopentene. Equilibration of the initial reaction mixtures at 25-50 degrees with excess diborane leads to the formation of mono-n-pentylborane and manocyclopentylborane in yields of 65 and 73170, respectively. These boranes are readily converted to the methyl esters by treatment with methanol, and the esters are readily converted to the correspondin g boronic acids by hydrolysis. Consequently, hydroboration of olefins provides a convenient synthetic route to the alkane and cycloalkane boronic and borinic acids and their derivatives.

  DOI：

  10.1021/ja01502a062

文献信息

• BROWN, H. C.;CHA, J. SOON;NAZER, BEHROOZ;KIM, SUK-CHOONG;KRISHNAMURTHY, S+, J. ORG. CHEM., 1984, 49, N 5, 885-892
  作者：BROWN, H. C.、CHA, J. SOON、NAZER, BEHROOZ、KIM, SUK-CHOONG、KRISHNAMURTHY, S+

  DOI：——

  日期：——
• Hydroboration. VI. A Convenient Synthesis of the Alkane and Cycloalkane Boronic and Borinic Esters and Acids
  作者：Herbert C. Brown、Akira Tsukamoto、D. B. Bigley

  DOI：10.1021/ja01502a062

  日期：1960.9

  The addition of I-pentene or cyclopentene to a solution of one-half the molar quantity of diborane in tetrahydroftiran solution at 0 degrees results in the formation of 60 to 65% yields of di-n-pentylborane and dicyclopentylborane, readily converted to the corresponding borinic methyl esters by treatment with methanol. Equilibration of the initial reaction mixture with a deficiency of diborane (2 olefin/1 BH3) leads to the preferred formation of di-n-pentylborane in the case of I-pentene, but to the preferred formation of monocyclopentylborane (and tricyclopentylborane) in the case of the cyclic olefin, cyclopentene. Equilibration of the initial reaction mixtures at 25-50 degrees with excess diborane leads to the formation of mono-n-pentylborane and manocyclopentylborane in yields of 65 and 73170, respectively. These boranes are readily converted to the methyl esters by treatment with methanol, and the esters are readily converted to the correspondin g boronic acids by hydrolysis. Consequently, hydroboration of olefins provides a convenient synthetic route to the alkane and cycloalkane boronic and borinic acids and their derivatives.
• ARASE, AKIRA;HOSHI, MASAYUKI;MASUDA, YUZURU, BULL. CHEM. SOC. JAP., 1984, 57, N 1, 209-213
  作者：ARASE, AKIRA、HOSHI, MASAYUKI、MASUDA, YUZURU

  DOI：——

  日期：——