dimethyl [2-(2,5-dimethoxyphenyl)-2-oxoethyl]phosphonate | 189625-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl [2-(2,5-dimethoxyphenyl)-2-oxoethyl]phosphonate
• 英文别名: dimethyl 2,5-dimethoxyphenacylphosphonate；Phosphonic acid, [2-(2,5-dimethoxyphenyl)-2-oxoethyl]-, dimethyl ester；1-(2,5-dimethoxyphenyl)-2-dimethoxyphosphorylethanone
• CAS: 189625-07-8
• 化学式: C₁₂H₁₇O₆P
• 分子量: 288.237
• InChiKey: IWJSGKHIYZEKPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl [2-(2,5-dimethoxyphenyl)-2-oxoethyl]phosphonate 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 [5-(2,5-Dimethoxy-phenyl)-furan-3-yl]-methanol
  参考文献：
  名称：

  A simple approach to 2-substituted-4-furanmethanol compounds

  摘要：

  A two step synthesis of the title compounds from easily available starting materials is reported. The method involves a Horner-Wadsworth-Emmons reaction between beta-ketophosphonates and 1,3-diacetoxy-2-propanone, followed by mild acid treatment of the gamma,gamma'-diacetoxyenones thus obtained. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00339-0
• 作为产物：
  描述：

  2-二甲氧基磷酸乙酸 、 对苯二甲醚 在 磷酸 、 三氟乙酸酐 作用下， 反应 24.0h， 以54%的产率得到dimethyl [2-(2,5-dimethoxyphenyl)-2-oxoethyl]phosphonate
  参考文献：
  名称：

  An Efficient Preparation of β-Aryl-β-ketophosphonates by the TFAA/H₃PO₄-Mediated Acylation of Arenes with Phosphonoacetic Acids

  摘要：

  [GRAPHICS]beta-Aryl-beta-ketophosphonates can be efficiently prepared in good yield by using a TFAA/85% H(3)PO(4)-mediated acylation of electron-rich arenes with phosphonoacetic acids. The conditions offer advantages over existing methods of preparing these useful compounds by not requiring the use of strong base, cryogenics, or an anhydrous and inert atmosphere. Furthermore, some functional groups not tolerated with the reaction conditions used in existing methods are compatible with the herein described conditions.

  DOI：

  10.1021/jo800973e

文献信息

• [EN] METHODS FOR PREPARING ARYL-SUBSTITUTED KETOPHOSPHONATES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE CÉTOPHOSPHONATES SUBSTITUÉS PAR DES GROUPES ARYLE
  申请人：NEUROGEN CORP

  公开号：WO2008097483A2

  公开（公告）日：2008-08-14

  [EN] Methods are provided for the synthesis of aryl-substituted ketophosphonates of the Formula (I): wherein variables are as described herein. Such compounds are useful as reagents for olefination reactions, and as intermediates in the synthesis of certain biologically active agents.
  [FR] La présente invention a trait à des procédés de synthèse de cétophosphonates substitués par des groupes aryle de formule (I), dans laquelle les variables sont telles que décrites dans les présentes. Lesdits composés se révèlent utiles en tant que réactifs pour les réactions d'oléfination et en tant qu'intermédiaires dans la synthèse de certains agents biologiquement actifs.
• An Efficient Preparation of β-Aryl-β-ketophosphonates by the TFAA/H₃PO₄-Mediated Acylation of Arenes with Phosphonoacetic Acids
  作者：George P. Luke、Christopher K. Seekamp、Zhe-Qing Wang、Bertrand L. Chenard

  DOI：10.1021/jo800973e

  日期：2008.8.1

  [GRAPHICS]beta-Aryl-beta-ketophosphonates can be efficiently prepared in good yield by using a TFAA/85% H(3)PO(4)-mediated acylation of electron-rich arenes with phosphonoacetic acids. The conditions offer advantages over existing methods of preparing these useful compounds by not requiring the use of strong base, cryogenics, or an anhydrous and inert atmosphere. Furthermore, some functional groups not tolerated with the reaction conditions used in existing methods are compatible with the herein described conditions.
• A simple approach to 2-substituted-4-furanmethanol compounds
  作者：Reyna Díaz-Cortés、Ana L. Silva、Luis A. Maldonado

  DOI：10.1016/s0040-4039(97)00339-0

  日期：1997.3

  A two step synthesis of the title compounds from easily available starting materials is reported. The method involves a Horner-Wadsworth-Emmons reaction between beta-ketophosphonates and 1,3-diacetoxy-2-propanone, followed by mild acid treatment of the gamma,gamma'-diacetoxyenones thus obtained. (C) 1997 Elsevier Science Ltd.