4-chloro-3-[(α-dimethoxyphosphoryl-α-hydroxy)methyl]coumarin | 677737-41-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-chloro-3-[(α-dimethoxyphosphoryl-α-hydroxy)methyl]coumarin
• 英文别名: 4-Chloro-3-[dimethoxyphosphoryl(hydroxy)methyl]chromen-2-one
• CAS: 677737-41-6
• 化学式: C₁₂H₁₂ClO₆P
• 分子量: 318.65
• InChiKey: GQBXDWHBQJREQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  151-153 °C
• 沸点：
  489.8±45.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-甲氧基乙胺 、 4-chloro-3-[(α-dimethoxyphosphoryl-α-hydroxy)methyl]coumarin 以 甲醇 为溶剂， 反应 2.0h， 以65%的产率得到4-(2-methoxyethylamino)-2-oxochromene-3-carbaldehyde
  参考文献：
  名称：

  Phosphorylation and Amine-induced Dephosphorylation of 4-Chlorocoumarin-3-carboxaldehyde and 4-Chloro-3-(β,β-dicyanoethenylidene)coumarin

  摘要：

  4-Chlorocoumarin-3-carboxaldehyde (1) and 4-chloro-3-(beta,beta-dicyanoethenylidene)coumarin (2) produce their respective 1:1 phosphonate adducts (5a-c) and (6a-c) upon reaction with the appropriate dialkylphosphonates (3a-c). Compounds 5 undergo dechlorination and dephosphorylation upon reaction with certain primary aliphatic amines to yield 9 (or 10) according to the nature of the amine used. Compounds 1 and 2 undergo dechlorination through reaction with hexamethyl-phosphorustriamide 4 to give the respective 4-dimethylamino-derivatives (11a and 11b). Structural reasonings for the new compounds are based on compatible analytical and spectroscopic measurements. The mechanism for formation of compounds 11 also is discussed.

  DOI：

  10.1080/713744562
• 作为产物：
  描述：

  4-氯-3-甲酰基香豆素 、 亚磷酸氢二甲酯 以80%的产率得到4-chloro-3-[(α-dimethoxyphosphoryl-α-hydroxy)methyl]coumarin
  参考文献：
  名称：

  Phosphorylation and Amine-induced Dephosphorylation of 4-Chlorocoumarin-3-carboxaldehyde and 4-Chloro-3-(β,β-dicyanoethenylidene)coumarin

  摘要：

  4-Chlorocoumarin-3-carboxaldehyde (1) and 4-chloro-3-(beta,beta-dicyanoethenylidene)coumarin (2) produce their respective 1:1 phosphonate adducts (5a-c) and (6a-c) upon reaction with the appropriate dialkylphosphonates (3a-c). Compounds 5 undergo dechlorination and dephosphorylation upon reaction with certain primary aliphatic amines to yield 9 (or 10) according to the nature of the amine used. Compounds 1 and 2 undergo dechlorination through reaction with hexamethyl-phosphorustriamide 4 to give the respective 4-dimethylamino-derivatives (11a and 11b). Structural reasonings for the new compounds are based on compatible analytical and spectroscopic measurements. The mechanism for formation of compounds 11 also is discussed.

  DOI：

  10.1080/713744562

文献信息

• Phosphorylation and Amine-induced Dephosphorylation of 4-Chlorocoumarin-3-carboxaldehyde and 4-Chloro-3-(β,β-dicyanoethenylidene)coumarin
  作者：Maha Darwish Khidre

  DOI：10.1080/713744562

  日期：2003.10.1

  4-Chlorocoumarin-3-carboxaldehyde (1) and 4-chloro-3-(beta,beta-dicyanoethenylidene)coumarin (2) produce their respective 1:1 phosphonate adducts (5a-c) and (6a-c) upon reaction with the appropriate dialkylphosphonates (3a-c). Compounds 5 undergo dechlorination and dephosphorylation upon reaction with certain primary aliphatic amines to yield 9 (or 10) according to the nature of the amine used. Compounds 1 and 2 undergo dechlorination through reaction with hexamethyl-phosphorustriamide 4 to give the respective 4-dimethylamino-derivatives (11a and 11b). Structural reasonings for the new compounds are based on compatible analytical and spectroscopic measurements. The mechanism for formation of compounds 11 also is discussed.