(3-Carboxy-phenyl)-diphenyl-phosphinoxid | 2129-29-5

• 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: (3-Carboxy-phenyl)-diphenyl-phosphinoxid
• 英文别名: 3-(diphenylphosphoryl)benzoic acid；Diphenyl-(m-carboxyphenyl)-phosphinoxid；3-Diphenylphosphorylbenzoic acid
• CAS: 2129-29-5
• 化学式: C₁₉H₁₅O₃P
• 分子量: 322.3
• InChiKey: ZENMDFRZJSUIQV-UHFFFAOYSA-N

物化性质

• 熔点：
  232 °C
• 沸点：
  570.4±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-Carboxy-phenyl)-diphenyl-phosphinoxid 在 劳森试剂 、 氯化亚砜 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 生成 2-[3-(diphenylthiophosphoryl)phenyl]-1,3-benzothiazole
  参考文献：
  名称：

  Thiophosphoryl-, Thiophosphoryloxy-, and Thiophosphorylamino-Benzene Derivatives as Novel Classes of Hybrid Pincer Ligands

  摘要：

  The synthetic approaches to novel families of SCE (E = S',N,O) hybrid pincer-type ligands bearing thophosphoryl, thiophosphoryloxy, and thiophosphorylamino groups in various combinations with thiophosphoryl-, thiocarbamoyl-, and imine- (including that of benzothiazole ring) donating functions have been developed. All of the ligands readily undergo direct cyclometallation (metal = Pd(II), Pt(II)) to afford 5,5- or 5,6-membered pincer complexes. Palladium complexes displayed from high to excellent catalytic performance in the Suzuki cross-coupling reaction of aryl bromides and phenylboronic acid and the higher asymmetry for a complex served as a factor of its higher catalytic activity.

  DOI：

  10.1080/10426507.2010.507726
• 作为产物：
  描述：

  3-二苯基磷烷基苯甲酸 在 水 、 2C₅₁H₃₉N₆⁽³⁺⁾*6Br^(1-)*3C₄₈H₄₈N₃₂O₁₆ 作用下， 以73 %的产率得到(3-Carboxy-phenyl)-diphenyl-phosphinoxid
  参考文献：
  名称：

  构建具有活性氧增强性能的超分子有机框架用于光催化有机转化

  摘要：

  超分子有机框架（SOF）的构建经常导致活性氧（ROS）生成效率的大幅降低。因此，创建和构建能够提高 ROS 生成效率的 SOF 光催化剂至关重要。在本研究中，我们开发并生产了化合物TN-3Ny，它是2,4,6-三(吡啶-4-基)-1,3,5-三嗪的衍生物。当该化合物与葫芦[8]脲（CB[8]）相互作用时，能够形成称为 TN-SOF 的超分子有机框架。 TN-3Ny 单体表现出产生单线态氧 (O) 和超氧阴离子自由基 (O) 的能力。由于大环主体分子和骨架结构的限制作用，CB[8]的掺入导致TN-SOF形成过程中产生O和O的效率显着提高。此外，利用O2和O2增强了三环己基膦和苯基硼酸的光催化氧化过程。与 TN-3Ny 单体相比，TN-SOF 表现出优异的光催化活性，因为它具有非凡的产生 O 和 O 的能力。因此，它在水溶液中实现了三环己基膦 91% 和苯基硼酸 90% 的令人印象深刻的产率通

  DOI：

  10.1016/j.mcat.2024.114153

文献信息

• Synthesis of water-soluble phosphine oxides by Pd/C-catalyzed P-C coupling in water
  申请人：Paul Scherrer Institut

  公开号：EP2626362A1

  公开（公告）日：2013-08-14

  Cross-coupling between diphenylphosphine oxide and halogenated benzoic acids catalyzed by Pd/C in water is a green, simple and fast protocol to obtain water-soluble tertiary phosphine oxides without the addition of ligands and additives. Low reaction times, microwave irradiation, and high substrate scope make this method general and excellent for lab- and large-scale synthesis without the need to use organic solvents for neither reaction nor workup.

  二苯基膦氧化物与卤代苯甲酸在水中由Pd/C催化的交叉偶联是一种绿色、简单和快速的方法，可获得可溶于水的三级膦氧化物，无需添加配体和添加剂。低反应时间、微波辐射和广泛的底物范围使得这种方法在实验室和大规模合成中通用且优秀，既不需要使用有机溶剂进行反应也不需要进行后处理。
• [EN] SYNTHESIS OF WATER-SOLUBLE PHOSPHINE OXIDES BY PD/C-CATALYZED P-C COUPLING IN WATER<br/>[FR] SYNTHÈSE D'OXYDES DE PHOSPHINE SOLUBLES DANS L'EAU PAR COUPLAGE P-C CATALYSÉ PAR PD/C DANS L'EAU
  申请人：SCHERRER INST PAUL

  公开号：WO2013117440A1

  公开（公告）日：2013-08-15

  Cross-coupling between diphenylphosphine oxide and halogenated benzoic acids catalyzed by Pd/C in water is a green, simple and fast protocol to obtain water-soluble tertiary phosphine oxides without the addition of ligands and additives. Low reaction times, microwave irradiation, and high substrate scope make this method general and excellent for lab- and large-scale synthesis without the need to use organic solvents for neither reaction nor workup.

  在水中，由Pd/C催化的二苯基膦氧化物与卤代苯甲酸之间的交叉偶联是一种绿色、简单且快速的协议，可获得可溶于水的三级膦氧化物，无需添加配体和添加剂。低反应时间、微波辐射和广泛的底物范围使得这种方法普适且非常适用于实验室和大规模合成，无需使用有机溶剂进行反应或工作。
• Synthesis of tertiary phosphine oxides by alkaline hydrolysis of quaternary phosphonium zwitterions using excess <i>t</i>-BuOK and stoichiometric water
  作者：Chun-Hong Zhong、Wenhua Huang

  DOI：10.1080/00397911.2020.1868006

  日期：——

  Abstract Hydrolysis of quaternary arylphosphonium zwitterions bearing COO− and those in situ generated from the corresponding salts bearing Ac or OH at the aryl ring by using excess t-BuOK and stoichiometric water affords tertiary arylphosphine oxides in moderate to excellent yield, in contrast to hydrolysis of these zwittertion or salts in aqueous NaOH that mainly provides phosphine oxides with the

  摘要 季芳基鏻两性离子轴承COO的水解-和那些在从轴承AC或OH在芳基环的相应的盐原位产生通过使用过量吨-BuOK和化学计量的水，得到的叔芳基膦氧化物在中度至良好产率，相反，这些水解在NaOH水溶液中的两性离子或盐，主要提供氧化膦，但失去了芳基。在t- BuOK /水条件下，部分以磷烯醇phospho形式存在的羰基稳定化的烷基化物Ph 3 P = CHCOR（R = Ph，Me和OEt）的水解更倾向于生成Ph 2 P（O）CH 2 COR。Ph 2 P（O）CH 2的进一步还原PhSiH 3的COMe可以43％的收率制备Ph 2 PCH 2 COMe。
• 새로운 구조의 포스포릴 유도체 및 이를 이용한 유기 전자 소자
  申请人：inje university industry-academic cooperation foundation 인제대학교 산학협력단(220050129079) BRN ▼615-82-06286

  公开号：KR20170034256A

  公开（公告）日：2017-03-28

  본 발명은 새로운 구조의 포스포릴 유도체 및 이를 이용한 유기 전자 소자에 관한 것으로, 보다 상세하게는 포스핀 옥사이드(phosphine oxide)와 옥사졸(oxazole), 이미다졸(imidazole), 싸이아졸(thiazole) 구조를 지닌 새로운 구조의 포스핀 유도체 및 이를 이용한 유기 전자 소자에 관한 것이다.

  这项发明涉及一种新型结构的磷氧化物衍生物以及用于有机电子器件的磷衍生物，更详细地说，涉及具有磷氧化物、氧唑、咪唑、噻唑结构的新型磷衍生物及其在有机电子器件中的应用。
• Synthesis of Water-Soluble Phosphine Oxides by Pd/C-Catalyzed P–C Coupling in Water
  作者：Stephan M. Rummelt、Marco Ranocchiari、Jeroen A. van Bokhoven

  DOI：10.1021/ol300582y

  日期：2012.4.20

  Cross-coupling between diphenylphosphine oxide and halogenated benzoic acids catalyzed by Pd/C in water is a green, simple, and fast protocol to obtain water-soluble tertiary phosphine oxides without the addition of ligands and additives. Low reaction times and microwave irradiation make this method general and excellent for laboratory and large-scale synthesis without the need to use organic solvents in reactions and workup.