3-fluorobenzylphosphonic acid dimethyl ester | 156745-61-8

• 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-fluorobenzylphosphonic acid dimethyl ester
• 英文别名: 3-Fluorobenzylphosphonic acid, dimethyl ester；1-(dimethoxyphosphorylmethyl)-3-fluorobenzene
• CAS: 156745-61-8
• 化学式: C₉H₁₂FO₃P
• 分子量: 218.165
• InChiKey: LQIMRRJDDSDSAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-fluorobenzylphosphonic acid dimethyl ester 在 dichlorobis(triethylphosphine)palladium(II) 、 氯化亚砜 、 potassium hydrogen bifluoride 、 N-乙酰-L-缬氨酸 、 N,N-二甲基甲酰胺 、 silver(l) oxide 作用下， 以 叔丁醇 为溶剂， 反应 27.0h， 生成 (5-Fluoro-2-phenylphenyl)methyl-methoxyphosphinic acid
  参考文献：
  名称：

  Palladium(II)-Catalyzed Ortho-Arylation of Benzylic Phosphonic Monoesters Using Potassium Aryltrifluoroborates

  摘要：

  The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed orthoarylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-arylation in high yields, and excellent functional group tolerance was also observed.

  DOI：

  10.1021/jo401716p
• 作为产物：
  描述：

  3-氟苄醇 、 三甲氧基磷 在 zinc(II) iodide 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 3-fluorobenzylphosphonic acid dimethyl ester
  参考文献：
  名称：

  Palladium(II)-Catalyzed Ortho-Arylation of Benzylic Phosphonic Monoesters Using Potassium Aryltrifluoroborates

  摘要：

  The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed orthoarylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-arylation in high yields, and excellent functional group tolerance was also observed.

  DOI：

  10.1021/jo401716p

文献信息

• Arylmethylphosphonates and phosphonic acids useful as anti-inflammatory
  申请人：The Upjohn Company

  公开号：US05593980A1

  公开（公告）日：1997-01-14

  This invention provides a new use of acids, esters, and salts of arylmethylphosphonates of Formula I, ##STR1## or a phosphonic acid of Formula II ##STR2## and derivatives as anti-inflammatory and anti-arthritic agents. Representative compounds include 4-dodecyloxybenzylphosphonic acid dimethyl ester, (2-naphthalenylmethyl)phosphonic acid dimethyl ester, and ([1,1'-biphenyl]-2-ylmethyl)phosphonic acid dimethyl ester.

  这项发明提供了一种新的使用方法，将公式I的芳基甲基膦酸酯和盐，或公式II的膦酸和衍生物用作抗炎和抗关节炎药物。代表性化合物包括4-十二烷氧基苯甲基膦酸二甲酯，(2-萘基甲基)膦酸二甲酯和([1,1'-联苯]-2-基)膦酸二甲酯。
• Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins
  作者：Jens Frackenpohl、Luka J.B. Decker、Jan Dittgen、Jörg Freigang、Pierre Génix、Hendrik Helmke、Gudrun Lange、Peter Luemmen、Jana Schmidt、Dirk Schmutzler、Jean-Pierre Vors

  DOI：10.1016/j.bmc.2020.115725

  日期：2020.11

  New phosphorous-containing lead structures against drought stress in crops interacting with RCAR/(PYR/PYL) receptor proteins were identified starting from in-depth SAR studies of related sulfonamide lead structures and protein docking studies. A converging 6-step synthesis via phosphinic chlorides and phosphono chloridates as key intermediates afforded envisaged tetrahydroquinolinyl phosphinamidates and phosphonamidates. Whilst tetrahydroquinolinyl phosphonamidates 13a,b exhibited low to moderate target affinities, the corresponding tetrahydroquinolinyl phosphinamidates 12a,b revealed confirmed strong affinities for RCAR/ (PYR/PYL) receptor proteins in Arabidopsis thaliana on the same level as essential plant hormone abscisic acid (ABA) combined with promising efficacy against drought stress in vivo (broad-acre crops wheat and canola).
• ARYLMETHYLPHOSPHONATES AND PHOSPHONIC ACIDS USEFUL AS ANTI-INFLAMMATORY AGENTS
  申请人：THE UPJOHN COMPANY

  公开号：EP0661978A1

  公开（公告）日：1995-07-12
• US5500417A
  申请人：——

  公开号：US5500417A

  公开（公告）日：1996-03-19
• [EN] ARYLMETHYLPHOSPHONATES AND PHOSPHONIC ACIDS USEFUL AS ANTI-INFLAMMATORY AGENTS<br/>[FR] ARYLMETHYLPHOSPHONATES ET ACIDES PHOSPHONIQUES UTILES EN TANT QU'AGENTS ANTI-INFLAMMATOIRES
  申请人：THE UPJOHN COMPANY

  公开号：WO1994007501A1

  公开（公告）日：1994-04-14

  (EN) This invention provides a new use of acids, esters, and salts of arylmethylphosphonates of formula (I) or phosphonic acids formula of (II) and derivatives as anti-inflammatory and anti-arthritic agents. Representative compounds include 4-dodecyloxybenzylphosphonic acid dimethyl ester, (2-naphthalenylmethyl)phosphonic acid dimethyl ester, and ([1,1'-biphenyl]-2-ylmethyl)phosphonic acid dimethyl ester. The invention also provides novel acids, esters, and salts of arylmethylphosphonic acid, phoshonic acid and derivatives.(FR) Nouvelle utilisation d'acides, d'esters et de sels d'arylméthylphosphonates de la formule (I) ou de l'acide phosphonique de la formule (II) et leurs dérivés en tant qu'agents anti-inflammatoires et antiarthritiques. Des composés représentatifs comprennent de l'ester diméthylique de l'acide 4-dodécyloxybenzylphosphonique, de l'ester diméthylique de l'acide (2-naphtalénylméthyl)phosphonique et de l'ester diméthylique d'acide ([1,1'-biphényl]-2-ylméthyl)phosphonique. La présente invention décrit également de nouveaux acides, esters et sels d'acide arylméthylphosphonique, d'acide phosphonique et de leurs dérivés.