(S)-(2-bromophenyl)phenyl(isopropyl)phosphine | 1383686-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(2-bromophenyl)phenyl(isopropyl)phosphine
• 英文别名: (S)-(2-bromophenyl)-phenyl-propan-2-ylphosphane
• CAS: 1383686-49-4
• 化学式: C₁₅H₁₆BrP
• 分子量: 307.17
• InChiKey: VZFXSXGDFALSQY-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (S)-(2-bromophenyl)-phenylisopropylphosphine borane 在 三乙烯二胺 作用下， 以 甲苯 为溶剂， 以82%的产率得到(S)-(2-bromophenyl)phenyl(isopropyl)phosphine
  参考文献：
  名称：

  基于Aryne化学的立体选择性合成邻溴（或碘）芳基P-发色性膦

  摘要：

  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。

  DOI：

  10.1021/jo300910w

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。
• P-CHIROGENIC ORGANOPHOSPHORUS COMPOUNDS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：US20140142325A1

  公开（公告）日：2014-05-22

  Novel P-chirogenic organophosphorus compounds of general formula (I), a process for the synthesis of the compounds of formula (I), and intermediate products of general formulae (II), (III) and (IV), as shown below, are involved in the synthesis of compounds (I). Metal complexes including compounds (I) as ligands are also described. The novel compounds and complexes are useful in asymmetric catalysis by transition metal complexes or organocatalysis, especially for asymmetric hydrogenation or allylation. Compounds of general formula (I) may be useful as agrochemical and therapeutic substances, or as reagents or intermediates for fine chemistry.

  通式为（I）的新型P-手性有机磷化合物的合成方法，以及通式为（II）、（III）和（IV）的中间体，如下所示，参与了化合物（I）的合成。还描述了以化合物（I）为配体的金属配合物。这些新型化合物和配合物在过渡金属配合物或有机催化剂的不对称催化中非常有用，特别是在不对称氢化或烯丙基化中。通式为（I）的化合物可能在农药和治疗物质中有用，或作为精细化学的试剂或中间体。
• US9186661B2
  申请人：——

  公开号：US9186661B2

  公开（公告）日：2015-11-17
• US9707553B2
  申请人：——

  公开号：US9707553B2

  公开（公告）日：2017-07-18
• 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.