(thexyl)2BH | 20622-63-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 饱和烃
• 英文名称: (thexyl)2BH
• 英文别名: dithexyl borane(3)；dithexylborane；Disiamylboran；Dithexylboran
• CAS: 20622-63-3
• 化学式: C₁₂H₂₇B
• 分子量: 182.157
• InChiKey: KVHVGMSSOIUZQH-UHFFFAOYSA-N

物化性质

• 沸点：
  217.7±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (thexyl)2BH 在 水 作用下， 生成 2,3-二甲基-2-丁醇
  参考文献：
  名称：

  Monomeric dialkylboranes

  摘要：

  DOI：

  10.1021/ja00766a070
• 作为产物：
  描述：

  2,3-二甲基-2-丁烯 生成 (thexyl)2BH
  参考文献：
  名称：

  Monomeric dialkylboranes

  摘要：

  DOI：

  10.1021/ja00766a070
• 作为试剂：
  描述：

  N-methyl-N'-propargyl diethylphosphoramidate 在 (thexyl)2BH 、 双氧水 、 sodium acetate 作用下， 生成 N-methyl diethylphosphoramidopropanal
  参考文献：
  名称：

  Baboulene, Michel; Lattes, Armand; Benmaarouf-Khallaayoun, Zahra, Synthetic Communications, 1990, vol. 20, # 14, p. 2091 - 2096

  摘要：

  DOI：

文献信息

• Hydroboration d'amines insaturees
  作者：Z. Benmaarouf-Khallaayoun、M. Baboulene、V. Speziale、A. Lattes

  DOI：10.1016/s0022-328x(00)98991-5

  日期：1986.6

  The regioselectivity and the stereoselectivity of the hydroboration of N-alkylallylphosphoramide was examined. This study shows the preferential formation of γ-boron derivatives (90 to 100%) and the excellent stereospecificity of the reaction (100% (Z) configuration).

  研究了N-烷基烯丙基磷酰胺的硼氢化的区域选择性和立体选择性。这项研究显示出优先形成γ-硼衍生物（90％至100％）和出色的反应立体定向性（100％（Z）构型）。
• Hydroboration d'amines insaturees—II
  作者：J.L. Torregrosa、M. Baboulene、V. Speziale、A. Lattes

  DOI：10.1016/0040-4020(82)87013-0

  日期：1982.1

  The hydroboration reaction of acetylenic amines R1R2NCH(R3)CCR4 was studied. We report the first results of a study of the reactivity of dialkylborane R2BH towards these amines which allow us to propose a new method for the synthesis of differently substituted β-ethylenic amines. The regioselectivity and the stereoselectivity of this reaction are examined and allow us to set out the possibility

  炔属胺R的硼氢化反应1 - [R 2 NCH（R 3）CCR 4进行了研究。我们报道了二烷基硼烷R 2 BH对这些胺的反应性研究的第一批结果，这使我们能够提出一种合成不同取代的β-亚乙基胺的新方法。研究了该反应的区域选择性和立体选择性，使我们能够提出反式硼氢化的可能性。
• 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.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.14, 4.3.3, page 179 - 181
  作者：

  DOI：——

  日期：——