5,7-dimethyl-2-ethoxy-1,2λ⁵-benzoxaphosphinine 2-oxide | 1571900-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 5,7-dimethyl-2-ethoxy-1,2λ⁵-benzoxaphosphinine 2-oxide
• 英文别名: 2-Ethoxy-5,7-dimethyl-1,2lambda5-benzoxaphosphinine 2-oxide；2-ethoxy-5,7-dimethyl-1,2λ5-benzoxaphosphinine 2-oxide
• CAS: 1571900-45-2
• 化学式: C₁₂H₁₅O₃P
• 分子量: 238.223
• InChiKey: FFVDKNDEOHIUJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,7-dimethyl-2-ethoxy-1,2λ⁵-benzoxaphosphinine 2-oxide 、 丙烯酸甲酯（MA） 在 silver(I) acetate 、 palladium diacetate 、 三甲基乙酸 作用下， 反应 13.0h， 以84%的产率得到(E)-methyl 2-ethoxy-5,7-dimethyl-2-oxo-2H-1,2-benzoxaphosphorine-3-acrylate
  参考文献：
  名称：

  Alkenylation of Phosphacoumarins via Aerobic Oxidative Heck Reactions and Their Synthetic Application to Fluorescent Benzophosphacoumarins

  摘要：

  Alkenylation of phosphacoumarins is developed from the reaction of phosphacoumarins with a variety of activated as well as nonactivated alkenes via aerobic oxidative Heck reactions. In addition, 3-alkenylphosphacoumarins undergo an inverse electron demand Diels-Alder reaction (IEDDA) with enamines in situ generated from ketone and pyrrolidine followed by 1,2-elimination and a dehydrogenation, producing fluorescent benzophosphacoumarins.

  DOI：

  10.1021/acs.orglett.5b00020
• 作为产物：
  描述：

  在 三苯基膦氯金 、 三氟甲磺酸 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 5,7-dimethyl-2-ethoxy-1,2λ⁵-benzoxaphosphinine 2-oxide
  参考文献：
  名称：

  金催化的芳基炔基膦酸酯的氢芳基化反应合成香豆香豆素。

  摘要：

  AbstractIntramolecular hydroarylation using aryl alkynylphosphonates proceeds smoothly with a gold/silver catalyst in the presence of trifluoromethanesulfonic acid (TfOH) in the 6‐endo mode, thus affording a unique synthetic method for phosphacoumarins having various functional groups, which could be a privileged structure and prevalent scaffold in phosphorus heterocycles.magnified image

  DOI：

  10.1002/adsc.201300545

文献信息

• Alkenylation of Phosphacoumarins via Aerobic Oxidative Heck Reactions and Their Synthetic Application to Fluorescent Benzophosphacoumarins
  作者：Cheol-Eui Kim、Jeong-Yu Son、Seohyun Shin、Boram Seo、Phil Ho Lee

  DOI：10.1021/acs.orglett.5b00020

  日期：2015.2.20

  Alkenylation of phosphacoumarins is developed from the reaction of phosphacoumarins with a variety of activated as well as nonactivated alkenes via aerobic oxidative Heck reactions. In addition, 3-alkenylphosphacoumarins undergo an inverse electron demand Diels-Alder reaction (IEDDA) with enamines in situ generated from ketone and pyrrolidine followed by 1,2-elimination and a dehydrogenation, producing fluorescent benzophosphacoumarins.
• Gold-Catalyzed Hydroarylation of Aryl Alkynylphosphonates for the Synthesis of Phosphacoumarins
  作者：Cheol-Eui Kim、Taekyu Ryu、Sanghyuck Kim、Kooyeon Lee、Chang-Hee Lee、Phil Ho Lee

  DOI：10.1002/adsc.201300545

  日期：2013.10.11

  AbstractIntramolecular hydroarylation using aryl alkynylphosphonates proceeds smoothly with a gold/silver catalyst in the presence of trifluoromethanesulfonic acid (TfOH) in the 6‐endo mode, thus affording a unique synthetic method for phosphacoumarins having various functional groups, which could be a privileged structure and prevalent scaffold in phosphorus heterocycles.magnified image