(R)-N-<1-(2-Naphthyl)propyl>-P,P-diphenylphosphinamide | 154851-91-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-<1-(2-Naphthyl)propyl>-P,P-diphenylphosphinamide
• 英文别名: N-[(1R)-1-(2-naphthyl)propyl]-P,P-diphenylphosphinic amide；N-[1-(2-naphthyl)propyl]-P,P-diphenylphosphinic amide；N-[1-(2-naphthyl)propyl]-P,P-diphenylphosphinoylamide；(R)-N-[1-(2-Naphthyl)propyl]-P,P-diphenylphosphinamide；Phosphinic amide, N-[(1R)-1-(2-naphthalenyl)propyl]-P,P-diphenyl-；(1R)-N-diphenylphosphoryl-1-naphthalen-2-ylpropan-1-amine
• CAS: 154851-91-9
• 化学式: C₂₅H₂₄NOP
• 分子量: 385.445
• InChiKey: IUGRYWWQBVAQRT-RUZDIDTESA-N

物化性质

• 熔点：
  105 °C
• 沸点：
  552.1±43.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  diethylzinc 、 (E)-N-(naphthalen-2-ylmethylene)-P,P-diphenylphosphinic amide 在 麻黄碱 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 (R)-N-<1-(2-Naphthyl)propyl>-P,P-diphenylphosphinamide 、 (S)-N-<1-(2-Naphthyl)propyl>-P,P-diphenylphosphinamide
  参考文献：
  名称：

  烷基苯作为溶剂在聚苯乙烯负载的麻黄碱与二乙基锌对N-二苯基膦亚基酰亚胺的对映选择性烷基化中的显著作用

  摘要：

  二乙基锌使用负载在聚苯乙烯上的手性麻黄碱使N-二苯基膦基嘧啶具有很高的对映选择性，烷基苯中反应的对映选择性大大高于单个芳族（苯）和脂族（己烷）烃的对映选择性。

  DOI：

  10.1039/c39940000317

文献信息

• Catalytic Enantioselective Addition of Dialkylzinc to <i>N</i>-Diphenylphosphinoylimines. A Practical Synthesis of α-Chiral Amines
  作者：Alessandro A. Boezio、André B. Charette

  DOI：10.1021/ja027673x

  日期：2003.2.19

  The enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoylimines derived from aryl-, furyl-, and cyclopropylaldehydes is efficiently catalyzed by a copper(II) triflate/(R,R)-MeDUPHOS complex. The yields are high (51-98%), and the enantiomeric excesses vary from 85 to 96%. This route provides a practical route to alpha-chiral amines.

  二烷基锌试剂与芳基-、呋喃基-和环丙醛衍生的 N-二苯基膦亚胺的对映选择性加成是由三氟甲磺酸铜 (II)/(R,R)-MeDUPHOS 复合物有效催化的。产率高 (51-98%)，对映体过量在 85% 至 96% 之间变化。该路线提供了获得 α-手性胺的实用路线。
• Polymer-supported l-prolinol-based catalysts for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinyl)imines
  作者：Raquel Almansa、Juan F. Collados、David Guijarro、Miguel Yus

  DOI：10.1016/j.tetasy.2012.12.007

  日期：2013.2

  Merrifield or Wang-type resins have been shown to form efficient catalysts for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinyl)imines. The enantioselectivity achieved with the polymeric catalyst (ee up to 88%) is slightly lower than the one obtained with the homogeneous ligand N-benzyl-l-prolinol, but the polymer-supported ligand presents the advantage of its recyclability: it

  已显示锚定在Merrifield或Wang型树脂上的基于1-Prolinol的配体可形成有效的催化剂，用于将二烷基锌试剂对映选择性地添加到N-（二苯基膦基）亚胺上。用聚合物催化剂实现的对映体选择性（ee最高可达88％）比用均相配体N-苄基-1-脯氨醇获得的对映体选择性略低，但聚合物负载的配体具有可回收性的优点：可以回收最多可用于六个连续的催化循环，对映体过量仅略有减少。作为加成产物获得的次膦酰胺可以在温和的酸性条件下转化为相应的对映体富集的α-支化伯胺。
• Enantioselective addition of dialkylzincs to N-diphenylphosphinylimines using polymer-supported N,N-dialkylnorephedrines as chiral ligands
  作者：Takefumi Suzuki、Takanori Shibata、Kenso Soai

  DOI：10.1039/a702139i

  日期：——

  Chiral N,N-dialkylnorephedrines supported on polystyrene resin catalyse the enantioselective addition of dialkylzincs to N-diphenylphosphinylimine, affording optically active N-diphenylphosphinylamines with high enantiomeric excess. The influence on the enantioselectivity of the carbon-chain spacer between the chiral function and polymer resin has been examined. Reaction temperature- and solvent-dependency on the chiral polymer-catalysed reaction has also been examined.

  负载于聚苯乙烯树脂上的手性N,N-二烷基去甲肾上腺素催化二烷基锌对手性N-二苯膦亚胺的立体选择性加成反应，生成高对映体过量率的光学活性N-二苯膦亚胺。考察了手性功能团与聚合物树脂之间的碳链间隔对对映选择性的影响。此外，还考察了反应温度和溶剂对这一手性聚合物催化反应的影响。
• Asymmetric Synthesis of N-(Diphenylphosphinyl)amines Promoted by Chiral Carbosilane Dendritic Ligands in The Enantioselective Addition of Dialkylzinc Compounds to N-(Diphenylphosphinyl)imines
  作者：Itaru Sato、Kenji Hosoi、Ryo Kodaka、Kenso Soai

  DOI：10.1002/1099-0690(200209)2002:18<3115::aid-ejoc3115>3.0.co;2-9

  日期：2002.9

  The enantioselective addition of dialkylzinc compounds to N-(diphenylphosphinyl)imines by using chiral dendrimers with flexible carbosilane backbones gives enantiomerically enriched N-(diphenylphosphinyl)amines with up to 92% ee. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  通过使用具有柔性碳硅烷主链的手性树枝状聚合物将二烷基锌化合物对映选择性加成到 N-（二苯基膦基）亚胺中，得到对映异构富集的 N-（二苯基膦基）胺，其 ee 高达 92%。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Asymmetric synthesis of N-diphenylphosphinoylamines by solvent-free enantioselective addition of dialkylzincs to N-diphenylphosphinoylimines
  作者：Itaru Sato、Ryo Kodaka、Kenso Soai

  DOI：10.1039/b106775n

  日期：2001.11.15

  Solvent-free enantioselective addition of dialkylzincs to N-diphenylphosphinoylimines in the presence of chiral 2-morpholino-1-phenylpropan-1-ol affords N-diphenylphosphinoylamines with up to 97% ee. The reaction in the solvent-free system is faster than in organic solvents.

  在手性2-吗啉代-1-苯基丙-1-醇的存在下，无溶剂条件下对N-二苯基膦酰亚胺进行二烷基锌的选择性不对称加成，可以得到最高达97% ee的N-二苯基膦酰胺。与有机溶剂相比，无溶剂体系中的反应速度更快。