(+)-(1S,2R)-2-dimethylamino-1-phenyl-1-diphenyl-phosphinoxy-propane | 76116-15-9

• 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: (+)-(1S,2R)-2-dimethylamino-1-phenyl-1-diphenyl-phosphinoxy-propane
• 英文别名: (+)O-diphenylphosphino N-methylephedrine；(1R,2S)-1-diphenylphosphanyloxy-N,N-dimethyl-1-phenylpropan-2-amine
• CAS: 76116-15-9
• 化学式: C₂₃H₂₆NOP
• 分子量: 363.439
• InChiKey: SZNYXGLRVCHCMJ-CVDCTZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2R)-2-dimethylamino-1-phenyl-1-diphenyl-phosphinoxy-propane 、 tetracarbonylhydridoferrate 以 四氢呋喃 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Aminophosphanes derived from chiral β-aminoalcohols and carbonyliron complexes thereof

  摘要：

  Phosphinites 2 and 4 derived from (-)-N-methylephedrine (1) and(+)-N-methyl-Psi-ephedrine (3), respectively are described. The synthesis of the chiral potassium hydridoferrate complex 8 from `N-methyl-diphenylephos' (2) and KHFe(CO)(4) was less selective than that of the previously described chiral zwitterionic hydride 7 from 'N,N-dimethyl-diphenylephosium' (6) and KHFe(CO)(4). Phosphines corresponding to deoxy derivatives of 'ephos' 2 and 'ephosium' 6 were envisaged. A stereoselective conversion of 2 to the hydrohexafluorophosphate of the N-methyl-diphenyldeoxyephos oxide isomer (5) is reported, and an approach to the 'N,N-dimethyl-diphenyldeoxyephosium? (A) has been explored by stereoselective chlorination of the quaternary N,N-dimethylephedrium (11). Likewise, 'N,N,N-trimethyl-diphenyldeoxyvalphosium' (B) was envisaged by chlorination of (+)-N,N,N-trimelhylvalinolium (14). In the presence of Ph2PLi, however, the chlorides 12a and 16 underwent elimination reactions instead of Cl- substitution, and the phosphines A and B did not form. In a reverse complexation-quaternization strategy, the 'N,N-dimethyl-diphenyldeoxyvalphos' - Fe(CO)(4) complex (20) has been selectively prepared and subsequently converted to the corresponding ammonium complexes 21 and 20.HOTf. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(99)00145-0
• 作为产物：
  描述：

  N-甲基麻黄碱 、 二苯基氯化膦 在 正丁基锂 作用下， 生成 (+)-(1S,2R)-2-dimethylamino-1-phenyl-1-diphenyl-phosphinoxy-propane
  参考文献：
  名称：

  Peyronel, Jean-Francois; Fiaud, Jean-Claude; Kagan, Henri B., Journal of Chemical Research, Miniprint, 1980, # 9, p. 4057 - 4080

  摘要：

  DOI：

文献信息

• Palladium(II) and platinum(II) complexes containing new phosphinoxy chiral P,N-ligands
  作者：Giancarlo Franciò、Carmela Grazia Arena、Manuela Panzalorto、Giuseppe Bruno、Felice Faraone

  DOI：10.1016/s0020-1693(97)06085-4

  日期：1998.7

  corresponding aminoalcohols. The reactions of the already reported ligand 2[1-phosphinoxy-1-(1S,2S,5R)-menthyl]pyridine (1) and of 2 and 3 with palladium(II) and platinum(II) substrates have been studied. The palladium complexes [Pd(1–3)Cl2] have been used as catalytic precursors in the asymmetric Grignard cross-coupling reaction between 1-phenylethyl magnesium bromide and vinyl bromide. Some considerations

  手性二苯基膦氧氧基P，N-配体（+）-（2 S，3 R）-4-二甲基氨基-3-甲基-1,2-二苯基-2-二苯基膦氧丁烷（2）和（+）-（1 S，2 R）-2-二甲基-氨基-1-苯基-1-二苯基次膦氧基丙烷（3）是从相应的氨基醇开始制备的。已经报道的配体2 [1-膦氧氧基-1-（1 S，2 S，5 R）-薄荷基]吡啶（1）以及2和3的配体与钯（II）和铂（II）的反应已经进行。研究过。钯配合物[Pd（1-3）Cl 2在二苯甲基溴化1-苯基乙基溴与乙烯基溴之间的不对称格利雅（Grignard）交叉偶联反应中，已使用溴化乙烯作为催化前体。提出了一些关于使用次膦氧基P，N-配体1-3的低对映选择性的考虑。为了验证在含有P，N-配体1-3的钯（II）和铂（II）配合物的亲核取代反应中的非对映选择性，配合物5、6、7和10与格氏试剂PhMeCHMgBr的反应外消旋形式的，未成功进行。[Pt（3）（Ph