Cyclohexyloxy-diethyl-borane | 108678-42-8

• 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: Cyclohexyloxy-diethyl-borane
• 英文别名: Cyclohexyl diethylborinate；cyclohexyloxy(diethyl)borane
• CAS: 108678-42-8
• 化学式: C₁₀H₂₁BO
• 分子量: 168.087
• InChiKey: NLWUHNYNWLDDID-UHFFFAOYSA-N

物化性质

• 沸点：
  211.6±7.0 °C(Predicted)
• 密度：
  0.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Cyclohexyloxy-diethyl-borane 在 双氧水 、 三乙胺 、 乙酰丙酮 作用下， 以 丙酮 为溶剂， 反应 9.0h， 生成 cyclohexyl diphenylphosphinate
  参考文献：
  名称：

  Dahlhoff, Wilhelm V.; Taba, Kalulu M., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 10, p. 1260 - 1262

  摘要：

  DOI：
• 作为产物：
  描述：

  三环己基氧基硼烷 、 乙基溴化镁 以 乙醚 为溶剂， 生成 Cyclohexyloxy-diethyl-borane
  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

• Boron Compounds; 69¹. Introduction and Removal of<i>t</i>-Butyldimethylsilyl Groups via Diethylboryloxy Compounds
  作者：Wilhelm V. Dahlhoff、Kalulu M. Taba

  DOI：10.1055/s-1986-31703

  日期：——

  O-Diethylboryl compounds react with t-butyldimethylsilylacetylacetonate in the presence of trimethylsilyl triflate at room temperature to give the corresponding t-butyldimethylsilyl ethers, which are easily deprotected, forming O-diethylboryl ethers on reaction with tetraethyldiboroxane.

  O-二乙基硼基化合物在三氟甲磺酸三甲基硅酯存在下与叔丁基二甲基甲硅烷基乙酰丙酮酯在室温下反应，得到相应的叔丁基二甲基甲硅烷基醚，该醚很容易脱保护，与四乙基二硼烷反应形成O-二乙基硼基醚。
• 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.
• Dahlhoff, Wilhelm V.; Taba, Kalulu M., Zeitschrift fur Naturforschung, B: Chemical Sciences, 1989, vol. 44, # 10, p. 1260 - 1262
  作者：Dahlhoff, Wilhelm V.、Taba, Kalulu M.

  DOI：——

  日期：——