phenylcyclohexylphosphine borane | 1383810-05-6

• 英文名称: phenylcyclohexylphosphine borane
• 英文别名: (cyclohexyl)phenylphosphine-borane；(R)-cyclohexylphenylphosphine borane
• CAS: 1383810-05-6；1383810-06-7；638166-55-9
• 化学式: C₁₂H₂₀BP
• 分子量: 206.076
• InChiKey: GMIWCJOTUUAFRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  phenylcyclohexylphosphine borane 、 6,7-dihydrodibenzo<1,3>diazonine 在 sodium hydride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 0.83h， 以69%的产率得到6-(cyclohexylphenylphosphanyl)-12,13-dihydro-5H-dibenzo[d,h][1,3]diazonine borane
  参考文献：
  名称：

  Synthesis of Phosphaguanidines by Hydrophosphination of Carbodiimides with Phosphine Boranes

  摘要：

  The direct addition of anionic secondary phosphine boranes to carbodiimides yields both chiral and achiral phosphaguanidine boranes, under ambient temperature conditions. An analogous preparation of menthol-derived phosphinite boranes is also described. These products can be deborinated to give the corresponding phosphines, and subsequently oxidized to give phosphine oxides. The robustness of this method was further demonstrated in the synthesis of structurally novel cyclic phosphaguanidines.

  DOI：

  10.1021/jo501841s
• 作为产物：
  描述：

  在 titanium(IV) isopropylate 、 盐酸 、 硼烷四氢呋喃络合物 、 1,1,3,3-四甲基二硅氧烷 、 水 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 phenylcyclohexylphosphine borane
  参考文献：
  名称：

  不对称的直接综合 二次膦 硼烷

  摘要：

  一锅法合成不对称烷基取代的 二次膦描述了氧化物。顺序添加N-苄基苯胺 解决 二氯苯基膦 和 1-甲基咪唑 在 甲基环己烷，分离形成的质子离子液体，添加 格氏试剂 其次是 水解 给不对称 二次膦氧化物（SPO）的高收率。在第一步中使用离子液体是必不可少的，它简化了合成过程。不对称的SPO可以量化为二次膦 用一个 催化 的数量 钛（O i Pr）4 和 四甲基二硅氧烷 （TMDS）在温和的反应条件下。

  DOI：

  10.1039/b920324a

文献信息

• Stereoselective Synthesis of <i>o</i>-Bromo (or Iodo)aryl P-Chirogenic Phosphines Based on Aryne Chemistry
  作者：Jérôme Bayardon、Hugo Laureano、Vincent Diemer、Mathieu Dutartre、Utpal Das、Yoann Rousselin、Jean-Christophe Henry、Françoise Colobert、Frédéric R. Leroux、Sylvain Jugé

  DOI：10.1021/jo300910w

  日期：2012.7.6

  tertiary phosphines bearing an o-bromo (or iodo)aryl substituent is described. The key step of this synthesis is based on the reaction of a secondary phosphine borane with the 1,2-dibromo (or diiodo)arene, owing to the formation in situ of an aryne species in the presence of n-butyllithium. When P-chirogenic secondary phosphine boranes were used, the corresponding o-halogeno-arylphosphine boranes were

  描述了带有邻-溴（或碘）芳基取代基的手性或非手性叔膦的有效合成。该合成的关键步骤基于仲膦硼烷与1,2-二溴（或二碘代）芳烃的反应，这是由于在正丁基锂的存在下原位形成了芳烃物种。当使用P-色原性仲膦硼烷时，获得了相应的邻卤代-芳基膦硼烷，而没有外消旋化，产率中等至良好，且ee高达99％。反应的立体化学完全保留了P原子上的构型，这是通过P-色原酸o的X射线结构确定的-卤代苯基膦硼烷配合物。无需使用DABCO进行消旋就可以轻松实现硼烷的分解，从而以高收率获得游离的邻-卤代-芳基膦。
• Novel Synthesis of P-Chiral Hydroxymethylphosphine–Boranes through Lipase-Catalyzed Optical Resolution
  作者：Kosei Shioji、Yoshimitsu Kurauchi、Kentaro Okuma

  DOI：10.1246/bcsj.76.833

  日期：2003.4

  A novel approach toward the lipase-catalyzed acylation of alkyl(1-hydroxymethyl)phosphine–boranes was achieved. Up to 99% of enantiomerically enriched phosphine–boranes was obtained by using lipase AK and CAL.

  实现了脂肪酶催化烷基（1-羟甲基）膦硼烷酰化的新方法。通过使用脂肪酶 AK 和 CAL，获得了高达 99% 对映体富集的膦硼烷。
• Efficient Stereoselective Synthesis of <i>o</i>-Functionalized P-Chirogenic Phosphines Applied to Asymmetric Catalysis
  作者：Jérôme Bayardon、Sylvain Jugé

  DOI：10.1080/10426507.2014.993760

  日期：2015.6.3

  The stereoselective synthesis of P-chirogenic o-halogenophenylphosphines and their use for the preparation of o-functionalized derivatives are reported. The key step of this synthesis is based on the reaction of a P-chirogenic secondary phosphine borane, previously prepared using ephedrine methodology, with n-butyllithium (1.2 equiv.) and 1,2-dihalogenobenzene. The reaction proceeds by addition of the phosphide borane to the benzyne generated in situ from 1,2-dihalogenobenzene by metal-halide exchange with the intermediate carbanion. The o-halogenophenylphosphine boranes were obtained with retention of configuration at the P-center and with enantioselectivities up to 99% ee. The free o-halogenophenylphosphines were applied for the preparation of various kinds of o-functionalized P-chirogenic phosphines useful in asymmetric catalyzed reactions.