(+/-)-(2-Hydroxyphenyl)methylphenylphosphine oxide | 99396-69-7

• 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: (+/-)-(2-Hydroxyphenyl)methylphenylphosphine oxide
• 英文别名: 2-(Methyl-phenyl-phosphinoyl)-phenol；2-[methyl(phenyl)phosphoryl]phenol
• CAS: 99396-69-7
• 化学式: C₁₃H₁₃O₂P
• 分子量: 232.219
• InChiKey: RXBAVVJCSXHILI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(2-Hydroxyphenyl)methylphenylphosphine oxide 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以64%的产率得到(+/-)-(2-Acetoxyphenyl)methylphenylphosphine oxide
  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
• 作为产物：
  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

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。
• Insertion of Arynes into P–O Bonds: One-Step Simultaneous Construction of C–P and C–O Bonds
  作者：Na Qi、Ning Zhang、Srinivasa Rao Allu、Jiangsheng Gao、Jian Guo、Yun He

  DOI：10.1021/acs.orglett.6b03283

  日期：2016.12.2

  The insertion of arynes into P–O bonds for the preparation of o-hydroxy-substituted arylphosphine oxides, -phosphinates, and -phosphonates is described. This novel reaction leads to the simultaneous formation of C–P and C–O bonds in one step with good yields and regioselectivities under mild and transition-metal-free conditions. The easy follow-up transformations of the resulting o-hydroxyl group extend

  描述了将芳烃插入到P–O键中以制备邻羟基取代的芳基膦氧化物，-次膦酸酯和-膦酸酯。这种新颖的反应可以一步一步同时形成C-P和C-O键，在温和且无过渡金属的条件下，具有良好的收率和区域选择性。所得邻羟基的容易的后续转化将这些反应扩展到其他邻位取代的芳基磷化合物的容易构造。
• N-Doped Semiconducting Material Comprising Phosphine Oxide Matrix and Metal Dopant
  申请人：NOVALED GMBH

  公开号：US20160322568A1

  公开（公告）日：2016-11-03

  The present invention relates to an electrically doped semiconducting material comprising at least one metallic element as n-dopant and at least one electron transport matrix compound comprising at least one phosphine oxide group, a process for its preparation, and an electronic device comprising the electrically doped semiconducting material.

  本发明涉及一种电掺杂半导体材料，包括至少一种金属元素作为n型掺杂剂和至少一种含有至少一个膦氧基团的电子传输基质化合物，以及其制备方法和包括该电掺杂半导体材料的电子器件。
• OPTICAL FUNCTIONAL LAMINATE
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：EP1738897A1

  公开（公告）日：2007-01-03

  There is provided a photofunctional laminated article being excellent in various photofunctionalities, particularly an intensity of light emission, light emitting efficiency and further fluorescence life and light amplifying property. The photofunctional laminated article comprises the transparent substrate (L0), the photofunctional layer (L1) comprising the fluorine-containing polymer (A) and the rare earth metal compound (B) and being formed on the substrate (L0) and the low refractive index layer (L2) formed on the photofunctional layer (L1), and when refractive indices of each layer are assumed to be n(L0), n(L1) and n(L2), the following equation: n(L0) ≥ n(L1) > n(L2) is satisfied.

  本发明提供了一种光功能层压制品，该制品具有各种优异的光功能，尤其是光发射强度、发光效率以及进一步的荧光寿命和光放大性能。该光电功能层压制品包括透明基底（L0）、由含氟聚合物（A）和稀土金属化合物（B）组成并形成于基底（L0）上的光电功能层（L1）以及形成于光电功能层（L1）上的低折射率层（L2），当各层的折射率假定为 n(L0)、n(L1) 和 n(L2)时，满足下式：n(L0) ≥ n(L1) > n(L2)。
• PHOTOFUNCTIONAL LAMINATE
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：EP1738897B1

  公开（公告）日：2011-02-09