Methoxydithexylboran | 36972-77-7

• 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: Methoxydithexylboran
• CAS: 36972-77-7
• 化学式: C₁₃H₂₉BO
• 分子量: 212.184
• InChiKey: KCNZFDVCMQQGRR-UHFFFAOYSA-N

物化性质

• 沸点：
  237.3±9.0 °C(Predicted)
• 密度：
  0.779±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 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：

  (thexyl)2BH 在 甲醇 作用下， 以 neat (no solvent) 为溶剂， 生成 Methoxydithexylboran
  参考文献：
  名称：

  Monomeric dialkylboranes

  摘要：

  DOI：

  10.1021/ja00766a070

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.14, 5, page 201 - 212
  作者：

  DOI：——

  日期：——
• Molecular Addition Compounds. 15. Synthesis, Hydroboration, and Reduction Studies of New, Highly Reactive <i>tert</i>-Butyldialkylamine−Borane Adducts
  作者：Herbert C. Brown、Josyula V. B. Kanth、Pramod V. Dalvi、Marek Zaidlewicz

  DOI：10.1021/jo990379b

  日期：1999.8.1

  Two series of tert-butyldialkylamines have been prepared and examined for borane complexation. The complexing ability of each amine in the two series examined decreases in the order shown. First series: t-BuN(CH2CH2)(2)O 1a > t-BuNEt2 Ib > t-BuNPr(2)(n)1c > t-BuN(CH2CH2OMe)(2) Id much greater than t-BuNBu2i le. Second series: t-(BuNBuMe)-Me-i 2a > t-(BuNPrMe)-Me-i 2b > t-(BuNBuEt)-Et-i 2c > t-(BuNBuPrn)-Pr-i 2d much greater than t-(BuNPrEt)-Et-i 2e. The reactivity of the corresponding borane adducts toward 1-octene increases in the reverse order. The following amines form highly reactive liquid borane adducts hydroborating 1-octene in tetrahydrofuran at room temperature in less than 1 h: t-BuN(CH2CH2OMe)(2), t-(BuNBuEt)-Et-i, and t-(BuNPrMe)-Me-i. The limit of borane complexation among the amines examined is reached for t-BuNBu2i exchanging borane neither with EMS nor with BH3-THF. Among the various borane adducts prepared, the more promising borane adducts, t-Bu(CH3OCH2CH2)(2)N-BH3 (7), t-(BuMePrN)-N-i-BH3 (8), and t-(BuEtBuN)-N-i-BH3 (9), were selected for complete hydroboration and reduction studies. Hydroboration studies with the new, highly reactive trialkylamine-borane adducts 7-9 and representative olefins, such as l-hexene, styrene, beta-pinene, cyclopentene, norbornene, cyclohexene, 2-methyl-2-butene, alpha-pinene, and 2,3-dimethyl-2-butene, in tetrahydrofuran, dioxane, tert-butyl methyl ether, n-pentane, and dichloromethane, at room temperature (22 +/- 3 degrees C) were carried out. The reactions are faster in dioxane, requiring 1-2 h for the hydroboration of simple, unhindered olefins to the trialkylborane stage. Moderately hindered olefins, such as cyclohexene and 2-methyl-2-butene, give the corresponding dialkylboranes rapidly, with further slow hydroboration. However, the more hindered olefins, alpha-pinene and 2,3-dimethyl-2-butene, give stable monoalkylboranes very rapidly, with further hydroboration proceeding relatively slowly. The hydroborations can also be carried out conveniently in other solvents, such as THF, tert-butyl methyl ether, and n-pentane. A significant; rate retardation is observed in dichloromethane. Regioselectivity studies of l-hexene and styrene using these amine-borane adducts show selectivities similar to that of BH3-THF. The rates and stoichiometry of the reaction of t-BuMePriN-BH3 in tetrahydrofuran with selected organic compounds containing representative functional groups were also examined at room temperature. The reductions of esters, amides, and nitriles, which exhibit a sluggish reaction at room temperature, proceed readily under reflux conditions in tetrahydrofuran and dioxane and without solvent (at 85-90 degrees C). The carrier amines can be recovered by simple acid-base manipulations in good yield and readily recycled to make the borane adducts.
• Hydroboration. XXXVII. Structural study of the hydroboration of olefins with thexylborane in the molar ratio of 1:1. Convenient synthesis of thexylmonoalkylboranes and their ready conversion to monoalkylboranes
  作者：Herbert C. Brown、Eiichi Negishi、Jean Jacques Katz

  DOI：10.1021/ja00843a030

  日期：1975.5