4-methoxylphenyl phosphonic acid monoethyl ester | 63818-65-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxylphenyl phosphonic acid monoethyl ester
• 英文别名: Ethoxy-(4-methoxyphenyl)phosphinic acid
• CAS: 63818-65-5
• 化学式: C₉H₁₃O₄P
• 分子量: 216.174
• InChiKey: OCJJSMKYZCOGBA-UHFFFAOYSA-N

物化性质

• 沸点：
  334.2±44.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxylphenyl phosphonic acid monoethyl ester 在 氯化亚砜 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 生成 (3R)-N-benzyloxy-2-[(RS)-ethoxy(4-methoxyphenyl)phosphoryl]-1,2,3,4-tetrahydroisoquinole-3-carboxamide
  参考文献：
  名称：

  Encounter with Unexpected Collagenase-1 Selective Inhibitor: Switchover of Inhibitor Binding Pocket Induced by Fluorine Atom

  摘要：

  Phosphonamide-based inhibitors having trifluoromethyl moiety showed highly selective inhibition against MMP-1. A possible mechanism of the selectivity of MMP-1 inhibitors through the switchover of the binding pocket was speculated by computational calculations. As a consequence of the unexpected selectivity, the specific interaction of CF3 group of the inhibitor and Arg214 in the S1' pocket of MMP-1 conducted a low binding energy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00796-x
• 作为产物：
  描述：

  4-甲氧苯基磷酸二氯 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 生成 4-methoxylphenyl phosphonic acid monoethyl ester
  参考文献：
  名称：

  Encounter with Unexpected Collagenase-1 Selective Inhibitor: Switchover of Inhibitor Binding Pocket Induced by Fluorine Atom

  摘要：

  Phosphonamide-based inhibitors having trifluoromethyl moiety showed highly selective inhibition against MMP-1. A possible mechanism of the selectivity of MMP-1 inhibitors through the switchover of the binding pocket was speculated by computational calculations. As a consequence of the unexpected selectivity, the specific interaction of CF3 group of the inhibitor and Arg214 in the S1' pocket of MMP-1 conducted a low binding energy. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00796-x

文献信息

• Rhodium-Catalyzed Oxidative Cyclization of Arylphosphonic Acid Monoethyl Esters with Alkenes: Efficient Synthesis of Benzoxaphosphole 1-Oxides
  作者：Taekyu Ryu、Jaeeun Kim、Youngchul Park、Sanghyuck Kim、Phil Ho Lee

  DOI：10.1021/ol401775t

  日期：2013.8.2

  Rhodium-catalyzed tandem oxidative alkenylation and an intramolecular oxy-Michael reaction were developed using arylphosphonic acid monoethyl esters and alkenes under aerobic conditions, which produced benzoxaphosphole 1-oxides in good to excellent yields.

  在有氧条件下，使用芳基膦酸单乙酯和烯烃开发了铑催化的串联氧化烯基化反应和分子内的氧-迈克尔反应，从而以良好的收率获得了良好的苯并恶唑1-氧化物。
• Rhodium-Catalyzed Oxidative C-H Activation/Cyclization for the Synthesis of Phosphaisocoumarins and Phosphorous 2-Pyrones
  作者：Youngchul Park、Jungmin Seo、Sangjune Park、Eun Jeong Yoo、Phil Ho Lee

  DOI：10.1002/chem.201302652

  日期：2013.11.25

  Rhodium‐catalyzed cyclization of phosphinic acids and phosphonic monoesters with alkynes has been developed. The oxidative annulation proceeds with complete conversion of phosphinic acid derivatives and allowed the atom‐economic preparation of useful phosphaisocoumarins with high yield and selectivity. The reaction is tolerant of extensive substitution on the phosphinic acid, phosphonic monoester and alkyne, including

  已经开发了炔烃对次膦酸和膦酸单酯进行铑催化的环化反应。氧化环化反应可进行次膦酸衍生物的完全转化，从而可以经济高效地制备有用的磷化异香豆素，并实现了原子经济的制备。该反应耐受在次膦酸，膦酸单酯和炔烃上的广泛取代，包括卤化物，酮和羟基作为取代基。此外，我们发现烯基膦酸单酯通过与炔烃的氧化环化作用继续生成各种磷2-吡喃酮。机理研究表明，CH键金属化是限速步骤。
• NOVEL PHOSPHININE OXIDE DERIVATIVE AND PREPARATION METHOD THEREOF
  申请人：KNU-INDUSTRY COOPERATION FOUNDATION

  公开号：US20150344506A1

  公开（公告）日：2015-12-03

  Provided are a novel phosphinine oxide derivative and a preparation method thereof, and more specifically, the phosphinine oxide derivative includes an oxaphosphinine oxide derivative and an azaphosphinine oxide derivative. The phosphinine oxide derivative according to the present invention may have a pharmacological activity and a physiological activity, and may be used as a basic framework of a natural product and may be used for development of new drug and synthesis of various medical supplies. In addition, according to the preparation method of the phosphinine oxide derivative according to the present invention, various phosphinine oxide derivatives with a high yield may be prepared by a simple synthesis process using an intramolecular annulation between a phosphinic derivative and an alkyne derivative in the presence of a rhodium (Rh) catalyst or a ruthenium (Ru) catalyst and an oxidant.

  提供了一种新型的膦氧衍生物及其制备方法，更具体地说，该膦氧衍生物包括氧代膦环氧衍生物和氮代膦环氧衍生物。根据本发明的膦氧衍生物可能具有药理活性和生理活性，并可用作天然产物的基本框架，可用于新药的开发和各种医疗用品的合成。此外，根据本发明的膦氧衍生物的制备方法，可以通过在铑（Rh）催化剂或钌（Ru）催化剂和氧化剂存在下使用磷酸衍生物和炔烃衍生物之间的分子内环化的简单合成过程来制备各种收率高的膦氧衍生物。
• Photoredox/Cobalt-Catalyzed Phosphinyloxy Radical Addition/Cyclization Cascade: Synthesis of Phosphaisocoumarins
  作者：Ming-Ming Qiao、Yi-Yin Liu、Sheng Yao、Tian-Cong Ma、Zi-Long Tang、De-Qing Shi、Wen-Jing Xiao

  DOI：10.1021/acs.joc.9b00570

  日期：2019.6.7

  A novel visible-light photoredox-catalyzed phosphinyloxy radical addition/cyclization cascade of arylphosphinic acids or arylphosphonic acid monoesters with alkynes has been developed, which provides an efficient and practical access to various phosphaisocoumarins by using a dual catalytic system containing an acridinium photosensitizer and a cobaloxime proton-reducing catalyst [Co(dmgH)2]PyCl at ambient

  已开发出一种新型的可见光光氧化还原催化的芳基次膦酸或芳基膦酸单酯与炔烃的次膦酰氧基自由基加成/环化级联反应，通过使用包含a啶光敏剂和钴肟的双催化体系，可以有效而实用地获得各种磷杂香豆素。室温下质子还原催化剂[Co（dmgH ）2 ] PyCl。该方法具有底物范围广，条件温和且无牺牲氧化剂的优点。
• Rhodium-catalyzed oxidative coupling through C–H activation and annulation directed by phosphonamide and phosphinamide groups
  作者：Sangjune Park、Boram Seo、Seohyun Shin、Jeong-Yu Son、Phil Ho Lee

  DOI：10.1039/c3cc44995e

  日期：——

  Rhodium-catalyzed oxidative coupling reactions via C-H activation and annulation directed by phosphonamide and phosphinamide groups were developed under aerobic conditions, which produced benzazaphosphole 1-oxides and phosphaisoquinolin-1-oxides.

  在好氧条件下，通过CH活化和膦酰胺和次膦酰胺基团的环化作用，进行了铑催化的氧化偶联反应，生成了苯并氮杂磷1氧化物和磷异喹啉1氧化物。