dihexylborane | 7178-61-2

• 分子结构分类: 有机化合物
• 英文名称: dihexylborane
• 英文别名: di-n-hexylborane；bis(1-hexyl)borane
• CAS: 7178-61-2
• 化学式: C₁₂H₂₇B
• 分子量: 182.157
• InChiKey: YXQCKJXKRAODSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  13
• 可旋转键数：
  10
• 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：

  dihexylborane 在 sodium hydroxide 、 三己基硼烷 、 双氧水 作用下， 以 乙醚 为溶剂， 生成 1,5-己二醇
  参考文献：
  名称：

  Vasil'ev,L.S. et al., Journal of general chemistry of the USSR, 1972, vol. 42, p. 1533 - 1538

  摘要：

  DOI：
• 作为产物：
  描述：

  1-己烯 在 bromoborane-dimethyl sulfide complex 、 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 dihexylborane
  参考文献：
  名称：

  Borenium Ion Catalyzed Hydroboration of Alkenes with N-Heterocyclic Carbene-Boranes

  摘要：

  Treatment of alkenes such as 3-hexene, 3-octene, and 1-cyclohexyl-1-butene with the N-heterocyclic carbene (NHC)-derived borane 2 and catalytic HNTf2 (Tf = trifluoromethanesulfonyl (CF3SO2)) effects hydroboration at room temperature. With 3-hexene, surprisingly facile migration of the boron atom from C(3) of the hexyl group to C(2) was observed over a time scale of minutes to hours. Oxidative workup gave a mixture of alcohols containing 2-hexanol as the major product. A similar preference for the C(2) alcohol was observed after oxidative workup of the 3-octene and 1-cyclohexyl-1-butene hydroborations. NHC-borenium cations (or functional equivalents) are postulated as the species that accomplish the hydroborations, and the C(2) selective migrations are attributed to the four center interconversion of borenium cations with cationic NHC-borane-olefin pi-complexes.

  DOI：

  10.1021/ja305061c

文献信息

• A STEREOSELECTIVE SYNTHESIS OF 1,2-DIALKYLETHENYL BROMIDES VIA MONOHYDROBORATION OF 1-BROMO-1-ALKYNES WITH DIALKYLBORANES
  作者：Yuzuru Masuda、Akira Arase、Akira Suzuki

  DOI：10.1246/cl.1978.665

  日期：1978.7.5

  Treatment of 1-bromo-1-alkenyldialkylboranes with lead(IV) acetate or iodosobenzene diacetate afforded 1-bromo-1,2-dialkylethylenes in moderate yields. Furthermore, both E-isomers and Z-isomers could be independently obtained as the main products by the use of different reaction conditions.

  用乙酸铅 (IV) 或碘代苯二乙酸酯处理 1-溴-1-烯基二烷基硼烷，以中等产率得到 1-溴-1,2-二烷基乙烯。此外，通过使用不同的反应条件，E-异构体和Z-异构体都可以作为主要产物独立获得。
• Singaram, Bakthan; Cole, Thomas E.; Brown, Herbert C., Organometallics, 1984, vol. 3, # 10, p. 1520 - 1523
  作者：Singaram, Bakthan、Cole, Thomas E.、Brown, Herbert C.

  DOI：——

  日期：——
• Cole, Thomas E.; Bakshi, Raman K.; Srebnik, Morris, Organometallics, 1986, vol. 5, # 11, p. 2303 - 2307
  作者：Cole, Thomas E.、Bakshi, Raman K.、Srebnik, Morris、Singaram, Bakthan、Brown, Herbert C.

  DOI：——

  日期：——
• Boroorganic compounds
  作者：L. S. Vasil'ev、M. M. Vartanyan、B. M. Mikhailov

  DOI：10.1007/bf02659538

  日期：1976.10
• The hydroboration of (trimethylsilyl)ethyne with dialkylboranes and its application to the syntheses of (E)-1-(trimethylsilyl)alk-1-enes and 2-(trimethylsilyl)alk-1-enes
  作者：Masayuki Hoshi、Yuzuru Masuda、Akira Arase

  DOI：10.1039/p19900003237

  日期：——

  The reaction of (trimethylsilyl)ethyne 1 with a stoicheiometric amount of dialkylborane 2 proceeds to the monohydroboration stage, giving a mixture of regioisomers, (E)-[2-(trimethylsilyl)-ethenyl]dialkylborane 3 and [1-(trimethylsilyl)ethenyl]dialkylborane 4. In the hydroboration with bulky dialkylboranes, derived from internal alkenes, the former predominates. Successive treatment of the mixture with methyllithium and benzenesulphenyl chloride exclusively affords highly pure (E)-2-alkyl-1-(trimethylsilyl)ethene 6 whose alkyl group migrates from the boron atom, while in the hydroboration with less bulky dialkylboranes, derived from terminal alkenes, the latter predominates. Successive treatment of the mixture with aq. NaOH and iodine exclusively affords highly pure 2-(trimethylsilyl)alk-1-ene 7 whose alkyl group migrates from the boron atom.