(S)-2-phenyl-4-[(diphenylphosphino)ethyl]oxazoline

• 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-phenyl-4-[(diphenylphosphino)ethyl]oxazoline
• 英文别名: diphenyl-[2-[(4S)-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl]ethyl]phosphane
• 化学式: C₂₃H₂₂NOP
• 分子量: 359.408
• InChiKey: ZAMPVULLYIIZJN-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  dimethyl benzoyl-L-aspartate 在 13 sodium tetrahydroborate 、 正丁基锂 、 三乙胺 、 calcium chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (S)-2-phenyl-4-[(diphenylphosphino)ethyl]oxazoline
  参考文献：
  名称：

  新型旋光性膦恶唑啉（JM-Phos）配体：烯丙基化反应的合成及应用。

  摘要：

  介绍了膦恶唑啉系统1的三种不同合成方法。这些方法中的两种是不同的途径，旨在涉及可以转化为几种不同最终产品的高级中间体。第三个是较短的途径，专门设计用于使用最少的官能团保护来促进大规模制备这些系统。总体上，制备了八种不同的膦恶唑啉。这些在几个钯介导的烯丙基化反应中筛选。事实证明，它们对于3-乙酰氧基-1,3-二苯基丙烯的不对称烷基化最有用，而对于更具挑战性的底物（戊烯基衍生物和环己烯基系统）则不太适用/不起作用。复合物[（η3-PhCHCHCHPh）Pd（1a）] [PF6]的X射线晶体学分析得出的结论是，这些系统中不对称诱导的起源可能间接归因于恶唑啉-苯基取代基与环氧基的相互作用。钯和烯丙基苯基取代基。最后，给出了N-酰基恶唑烷酮的甲硅烷基烯丙基化的数据。获得了极好的对映选择性和产率。

  DOI：

  10.1021/jo001333h

文献信息

• JM-PHOS Ligands:  Second-Generation Phosphine Oxazolines for Asymmetric Catalysis
  作者：Duen-Ren Hou、Kevin Burgess

  DOI：10.1021/ol991008k

  日期：1999.12.1

  [GRAPHICS]A small library of phosphine oxazoline ligands 2 was prepared and tested in palladium mediated allylation processes (reactions 1 and 2). They were found to be superior to the first generation ligands 1 and as effective as the well known phosphine oxazolines 3.
• NOVEL LIGANDS FOR CHIRAL CATALYSIS
  申请人：THE TEXAS A&M UNIVERSITY SYSTEM

  公开号：EP1165574A1

  公开（公告）日：2002-01-02
• US6472533B1
  申请人：——

  公开号：US6472533B1

  公开（公告）日：2002-10-29
• [EN] NOVEL LIGANDS FOR CHIRAL CATALYSIS<br/>[FR] NOUVEAUX LIGANDS POUR CATALYSE CHIRALE
  申请人：TEXAS A & M UNIV SYS

  公开号：WO2000061589A1

  公开（公告）日：2000-10-19

  Novel phosphine oxazoline ligands of formula (I) wherein m is 1, 2, 3 or 4; n, p, q, r are independently zero or 1 provided that at least one of n, p, q and r is 1; X is O, S, Se, CH2, NH; Y is N, P, As, S; R is H; a straight-chain alkyl group, a branched-chain alkyl group or a cyclo alkyl group optionally substituted by one or more groups independently selected from alkyl, aryl, halo, alkoxy, amine, phosphine and ether groups; an aryl group optionally substituted by one or more groups independently selected from alkyl, aryl, halo, alkoxy, amine, phosphine and ether groups; ferrocenyl; a thioalkyl group; a thioaryl group; or R is derived from a hydrocarbyl group attached to a functional group of an organic compound or a polymer capable of giving rise to the grouping -N-C-X- in the ring structure of (I); R?1 to R13¿ are independently selected from H; a straight-chain alkyl group, a branched-chain alkyl group or a cyclo alkyl group optionally substituted by one or more groups independently selected from alkyl, aryl, halo, alkoxy, amine, phosphine and ether groups; an aryl group optionally substituted by one or more groups independently selected from alkyl, aryl, halo, alkoxy, amine, phosphine and ether groups; with the proviso that when m is 1, one of n, p, q and r is 1 the remaining three being zero, X is O, Y is P, R?1 and R2¿ are both H, R?3 to R11¿ if present are H, and R?12 and R13¿ are both phenyl, then R is not CH¿3?, C(CH3)3, CHPh2, CPh3, adamantyl, C6H3(t-Bu)2, ferrocenyl, CF3, Ph, C6H4OMe, C6H4Me, C6H4NO2 or C6F5, a process for the preparation thereof, metal complexes containing such ligands and the use of such complexes, or combinations of ligand with metal salts or complexes, as catalysts for asymmetric syntheses.
• New, Optically Active Phosphine Oxazoline (JM-Phos) Ligands:  Syntheses and Applications in Allylation Reactions
  作者：Duen-Ren Hou、Joseph H. Reibenspies、Kevin Burgess

  DOI：10.1021/jo001333h

  日期：2001.1.1

  palladium-mediated allylation reactions. They proved to be most useful for asymmetric alkylation of 3-acetoxy-1,3-diphenylpropene and less suitable/effective for the more challenging substrates (a pentenyl derivative and a cyclohexenyl system). X-ray crystallographic analysis of the complex [(eta 3-PhCHCHCHPh)Pd(1a)][PF6] led to the conclusion that the origins of asymmetric induction in these systems

  介绍了膦恶唑啉系统1的三种不同合成方法。这些方法中的两种是不同的途径，旨在涉及可以转化为几种不同最终产品的高级中间体。第三个是较短的途径，专门设计用于使用最少的官能团保护来促进大规模制备这些系统。总体上，制备了八种不同的膦恶唑啉。这些在几个钯介导的烯丙基化反应中筛选。事实证明，它们对于3-乙酰氧基-1,3-二苯基丙烯的不对称烷基化最有用，而对于更具挑战性的底物（戊烯基衍生物和环己烯基系统）则不太适用/不起作用。复合物[（η3-PhCHCHCHPh）Pd（1a）] [PF6]的X射线晶体学分析得出的结论是，这些系统中不对称诱导的起源可能间接归因于恶唑啉-苯基取代基与环氧基的相互作用。钯和烯丙基苯基取代基。最后，给出了N-酰基恶唑烷酮的甲硅烷基烯丙基化的数据。获得了极好的对映选择性和产率。