(+/-)-(2-Hydroxyphenyl)methylphenylphosphine | 160797-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (+/-)-(2-Hydroxyphenyl)methylphenylphosphine
• 英文别名: 2-[Methyl(phenyl)phosphanyl]phenol
• CAS: 160797-87-5
• 化学式: C₁₃H₁₃OP
• 分子量: 216.219
• InChiKey: JAMHTCVDJSZOIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-(2-Hydroxyphenyl)methylphenylphosphine 在 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (+/-)-(2-Hydroxyphenyl)methylphenylphosphine oxide
  参考文献：
  名称：

  A simple chiral shift reagent for measurement of enantiomeric excesses of phosphine oxides

  摘要：

  DOI：

  10.1016/s0040-4039(00)98126-7
• 作为产物：
  描述：

  (o-methoxyphenyl)methylphenylphosphine 在 氢溴酸 作用下， 反应 12.0h， 以75%的产率得到(+/-)-(2-Hydroxyphenyl)methylphenylphosphine
  参考文献：
  名称：

  Kinetic Resolution of Phosphines and Phosphine Oxides with Phosphorus Stereocenters by Hydrolases

  摘要：

  Lipase from Candida rugosa (CRL) and cholesterol esterase (CE) catalyzed the enantioselective hydrolysis of pendant acetates in chiral phosphines and phosphine oxides. The enantioselectivity for most substrates was modest (E = 1.5-4.8), but both hydrolases showed high enantioselectivity for one substrate, ArPhMeP=O (Ar = 1-(2-acetoxy)naphthyl, 4c), E = 81 (CRL) and 32 (GE). Preparative-scale resolution of (+/-)-4c (1.0 g) catalyzed by CRL yielded enantiomerically-enriched starting acetate, (S)-(+)-4c, 0.48 g, 90% ee as well as product alcohol, (R)(-)-4b (Ar = 1-(2-hydroxy)naphthyl), 0.39 g, 88% se. Recrystallization of 4b from toluene raised the enantiomeric purity to >95% ee. Standard chemical steps followed by stereospecific reduction gave both enantiomers of phosphine ArPhMeP (Ar = 1-(2-methoxy)naphthyl) with 96-97% ee. This phosphine is an analog of PAMP (Ar = 2-methoxyphenyl), a chiral phosphine used in asymmetric synthesis.

  DOI：

  10.1021/jo00104a015

文献信息

• NEW ORTHO-FUNCTIONALIZED P-CHIRAL ARYLPHOSPHINES AND DERIVATIVES: THEIR PREPARATION AND USE IN ASYMMETRIC CATALYSIS
  申请人：Stephan Michel

  公开号：US20100099875A1

  公开（公告）日：2010-04-22

  The invention relates to novel organo phosphorus P-chiral optically active compounds of formula (I) having a hydroxyl, mercapto, amino, carboxyl, sulfonyl group on aryl near a phosphorus atom, to the preparation and the use thereof in then asymmetrical catalysis of unsaturated compounds. Novel acylphosphine optically pure ligands embodied in the form of transition metal complexes exhibit an increased activity and enantloselectivity, in particular in asymmetrical hydrogenation, in comparison with the same type Uganda such as DiPAMP.

  该发明涉及具有化学式（I）的新型有机磷P-手性光学活性化合物，其在含磷原子附近的芳基上具有羟基、巯基、氨基、羧基、磺酰基基团，以及其在不对称催化不饱和化合物中的制备和使用。新型酰基膦光学纯配体以过渡金属配合物的形式体现，与同类型的乌干达化合物（如DiPAMP）相比，在不对称氢化等反应中表现出增强的活性和对映选择性。
• Ethylene oligomerization process
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0128596B1

  公开（公告）日：1987-05-20
• NOUVELLES ARYLPHOSPHINES P-CHIRALES ORTHO-FONCTIONNALISEES ET DERIVES: LEUR PREPARATION ET UTILISATION EN CATALYSE ASYMETRIQUE
  申请人：Phosphoenix SARL

  公开号：EP1899358A2

  公开（公告）日：2008-03-19
• Phosphinyl Amidine Compounds, Metal Complexes, Catalyst Systems, and Their Use to Oligomerize or Polymerize Olefins
  申请人：Chevron Phillips Chemical Company LP

  公开号：US20170305945A1

  公开（公告）日：2017-10-26

  N 2 -phosphinyl amidine compounds, N 2 -phosphinyl amidinates, N 2 -phosphinyl amidine metal salt complexes, N 2 -phosphinyl amidinate metal salt complexes are described. Methods for making N 2 -phosphinyl amidine compounds, N 2 -phosphinyl amidinates, N 2 -phosphinyl amidine metal salt complexes, and N 2 -phosphinyl amidinate metal salt complexes are also disclosed. Catalyst systems utilizing the N 2 -phosphinyl amidine metal salt complexes and N 2 -phosphinyl amidinate metal salt complexes are also disclosed along with the use of the N 2 -phosphinyl amidine compounds, N 2 -phosphinyl amidinates, N 2 -phosphinyl amidine metal salt complexes, and N 2 -phosphinyl amidinate metal salt complexes for the oligomerization and/or polymerization of olefins.
• US4472525A
  申请人：——

  公开号：US4472525A

  公开（公告）日：1984-09-18