(S)-N-[1-(biphenyl-4-yl)-1-phenylmethyl]-P,P-diphenylphosphinamide | 1190207-24-9

• 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)-N-[1-(biphenyl-4-yl)-1-phenylmethyl]-P,P-diphenylphosphinamide
• 英文别名: (-)-(S)-N-[biphenyl-4-yl(phenyl)methyl]-P,P-diphenylphosphinic amide；(1S)-N-diphenylphosphoryl-1-phenyl-1-(4-phenylphenyl)methanamine
• CAS: 1190207-24-9
• 化学式: C₃₁H₂₆NOP
• 分子量: 459.527
• InChiKey: CQASFSISFRONKU-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-[1-(biphenyl-4-yl)-1-phenylmethyl]-P,P-diphenylphosphinamide 在 盐酸 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 14.0h， 以97%的产率得到(S)-(-)-α-(4-biphenylyl)benzylamine
  参考文献：
  名称：

  Steric Tuning of the Amidomonophosphane-Rhodium(I) Catalyst in Asymmetric Addition of Arylboroxines to N-Phosphinoyl Aldimines

  摘要：

  Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-phosphinoylaldi mines was realized by the steric tuning of a cliphenylphosphorus moiety to a di(o-tolyl) phosphorus moiety of a chiral amidomonophosphane. The presence of MS 4 A in a 5:1 solvent mixture of dioxane-propanol was essential to afford the corresponding diarylmethylamines in high yield.

  DOI：

  10.1021/ol901866y
• 作为产物：
  描述：

  N-亚苄基-P,P-二苯基次膦酸酰胺 、 2,4,6-tris([1,1'-biphenyl]-4-yl)boroxine 在 acetylacetonatobis(ethylene)rhodium(I) 、 tert-butyl N-{1-(R)-[(2-(S)-bis(2-methylphenyl)phosphinomethyl)pyrrolidine-1-carbonyl]-2-methylpropyl}-carbamate 作用下， 以 1,4-二氧六环 、 丙醇 为溶剂， 反应 12.0h， 以93%的产率得到(S)-N-[1-(biphenyl-4-yl)-1-phenylmethyl]-P,P-diphenylphosphinamide
  参考文献：
  名称：

  Steric Tuning of the Amidomonophosphane-Rhodium(I) Catalyst in Asymmetric Addition of Arylboroxines to N-Phosphinoyl Aldimines

  摘要：

  Highly enantioselective rhodium-catalyzed addition of arylboroxines to N-phosphinoylaldi mines was realized by the steric tuning of a cliphenylphosphorus moiety to a di(o-tolyl) phosphorus moiety of a chiral amidomonophosphane. The presence of MS 4 A in a 5:1 solvent mixture of dioxane-propanol was essential to afford the corresponding diarylmethylamines in high yield.

  DOI：

  10.1021/ol901866y

文献信息

• Steric influence of N-phosphorus-arylimines on the rhodium-catalyzed asymmetric arylation
  作者：Xinyu Hao、Qian Chen、Ken-ichi Yamada、Yasutomo Yamamoto、Kiyoshi Tomioka

  DOI：10.1016/j.tet.2011.06.033

  日期：2011.9

  Examination of the rhodium-catalyzed asymmetric arylation of benzaldehyde-imines bearing ethoxy, isopropoxy, phenyl, cyclohexyl, 3,5-xylyl, and 2,4,6-mesityl N-phosphorus activating/protecting groups revealed that bulky N-phosphorus groups retarded the arylation and at the same time prevented the competitive hydrolysis of an imine. Although the level of enantioselectivity was dependent favorably on

  铑催化的带有乙氧基，异丙氧基，苯基，环己基，3,5-二甲苯基和2,4,6-间苯三甲酰N-磷活化/保护基的苯甲醛-亚胺的铑不对称芳基化反应表明，庞大的N-磷基团被阻滞了芳基化，同时阻止了亚胺的竞争性水解。尽管对映选择性水平良好地依赖于从88％ee至53％ee的膨松度，但是反应性随着蓬松度从95％至3％而急剧降低。