6-bromo-3-(diphenylphosphoryl)-2H-chromen-2-one | 138116-15-1

• 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: 6-bromo-3-(diphenylphosphoryl)-2H-chromen-2-one
• 英文别名: 6-bromo-3-diphenylphosphorylchromen-2-one
• CAS: 138116-15-1
• 化学式: C₂₁H₁₄BrO₃P
• 分子量: 425.218
• InChiKey: SWNYXOUJFMCZOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.28
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  乙基(二苯基磷酰)乙酸酯 、 2-O-acetyl-4-bromosalicylaldehyde 在 盐酸 、 sodium hydroxide 作用下， 生成 6-bromo-3-(diphenylphosphoryl)-2H-chromen-2-one
  参考文献：
  名称：

  Phosphonates and phosphine oxides as reagents in a one-pot synthesis of coumarins

  摘要：

  Diethyl coumarin-3-phosphonates and Diphenyl coumarin-3-phosphinyloxide are obtained in mild conditions in one step, from acetoxysalicylaldehydes and triethyl phosphonoacetate or diphenyl phosphinyloxide acetate, by the use of a liquid/liquid phase transfer process without catalysor.

  DOI：

  10.1016/s0040-4039(00)92380-3

文献信息

• Direct Phosphonation of Quinolinones and Coumarins Driven by the Photochemical Activity of Substrates and Products
  作者：Inwon Kim、Minsik Min、Dahye Kang、Kiho Kim、Sungwoo Hong

  DOI：10.1021/acs.orglett.7b00299

  日期：2017.3.17

  Light-promoted phosphonation of quinolinones and coumarins was developed without the need for an external photocatalyst. Investigations support a mechanism whereby both starting materials and products act as photosensitizers upon excitation using compact fluorescent light sources to photochemically promote the dissociation of the N-O bond in the pyridinium salt by a single electron transfer pathway. A wide range of quinolinone and coumarin substrates can be utilized in the phosphonation process under mild reaction conditions.