N-[(1R)-1-(2-furyl)propyl]-P,P-diphenylphosphinic amide

• 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: N-[(1R)-1-(2-furyl)propyl]-P,P-diphenylphosphinic amide
• 英文别名: (R)-N-[1-(2-furyl)propyl]-P,P-diphenylphosphinoylamide；N-[1-(2-furyl)propyl]-P,P-diphenylphosphinoylamide；(R)-N-[1-(2-Furyl)propyl]-P,P-diphenylphosphinamide；(1R)-N-diphenylphosphoryl-1-(furan-2-yl)propan-1-amine
• 化学式: C₁₉H₂₀NO₂P
• 分子量: 325.347
• InChiKey: HVVDHYNSEXNHLN-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  diethylzinc 、 (E)-N-(furan-2-ylmethylene)-P,P-diphenylphosphinicamide 在 polystyrene-(1R,2S)-ephedrine-based dendrimer 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 N-[(1R)-1-(2-furyl)propyl]-P,P-diphenylphosphinic amide 、 N-[(1S)-1-(2-furyl)propyl]-P,P-diphenylphosphinic amide
  参考文献：
  名称：

  带有树枝状手性麻黄碱部分的新型定义明确的链端官能化聚苯乙烯的合成及其作为高对映选择性二乙基锌的N-二苯基膦酰基芳嘌呤类化合物的应用

  摘要：

  定量合成了一系列新颖的，定义明确的，具有2、4、8和16个手性麻黄碱部分在其超支化链端分布的手性麻油碱部分的链端官能化聚苯乙烯。通过元素分析，FTIR，SEC以及1 H和13 C NMR光谱学充分证实了它们的明确定义的体系结构。这些聚合物的分子量和分子量分布均得到精确控制，链端官能团也得到了明确定义。这些树状手性聚合物在二乙基锌向一系列N的对映选择性加成中充当高度对映选择性的手性配体-二苯基膦酰基芳基丙氨酸。其中，在链末端具有八个麻黄碱部分的手性树枝状聚合物以高至高收率提供了对映异构体富集的膦酰基酰胺，其对映选择性高达93％ee。所获得的对映选择性与使用N-苄基麻黄碱及其相应的共聚物作为手性配体所获得的对映选择性相当。

  DOI：

  10.1016/j.tet.2007.08.093

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。
• 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。
• Catalytic asymmetric diethylzinc addition to diphenylphosphionyl imines using chiral tert-butanesulfinylphosphine ligands
  作者：Junmin Chen、Dong Li、Haifeng Ma、Linfeng Cun、Jin Zhu、Jingen Deng、Jian Liao

  DOI：10.1016/j.tetlet.2008.09.111

  日期：2008.11

  A class of novel chiral tert-butanesulfinylphosphine ligands were designed and synthesized by a concise two-step route with high yields. High activities and enantioselectivities (up to 94% ee) were achieved when using them in catalytic asymmetric diethylzinc addition to diphenylphosphionyl imines.

  通过简洁的两步法设计并合成了高收率的一类新型手性叔丁烷亚磺酰基膦配体。当将它们用于二苯基膦酰亚胺的催化不对称二乙基锌中时，可实现高活性和对映选择性（高达94％ee）。
• Highly enantioselective addition of diethylzinc to N-diphenylphosphinylimines using dendritic chiral ligands with hydrocarbon backbones
  作者：Itaru Sato、Ryo Kodaka、Takanori Shibata、Yutaka Hirokawa、Nobuaki Shirai、Koji Ohtake、Kenso Soai

  DOI：10.1016/s0957-4166(00)00194-4

  日期：2000.6

  Chiral dendrimers bearing three or six chiral B-amino alcohols on the hyperbranched hydrocarbon chain-ends act as efficient chiral ligands for the enantioselective addition of diethylzinc to N-diphenyl-phosphinylimines to afford enantiomerically enriched N-diphenylphosphinylamines with up to 94% e.e. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Novel chiral copper complexes of N,P-ferrocenyl ligands with central and planar chirality as efficient catalyst for asymmetric addition of diethylzinc to imines
  作者：Min-Can Wang、Lan-Tao Liu、Yuan-Zhao Hua、Jun-Song Zhang、Yan-Yan Shi、De-Kun Wang

  DOI：10.1016/j.tetasy.2005.06.005

  日期：2005.8

  A new type of chiral copper complexes of N,P-ferrocenyl ligands with central and planar chirality as efficient catalyst was applied to the enantioselective addition of diethylzinc to N-diphenylphosphinoylimines. The (R)- and (s)-enantiomers of the addition reaction were obtained for this transformation. In the presence of 6 mol % of bidentate ligand 1 and 12 mol % of Cu(OTf)(2), the asymmetric addition process affords N-diphenylphosphinoylamides in up to 97% ee and 95% yields. (c) 2005 Elsevier Ltd. All rights reserved.