4-[2-(4-chlorophenyl)ethenyl]-7-hydroxychromen-2-one | 265986-71-8

• 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-[2-(4-chlorophenyl)ethenyl]-7-hydroxychromen-2-one
• CAS: 265986-71-8
• 化学式: C₁₇H₁₁ClO₃
• 分子量: 298.726
• InChiKey: CZBXMHGXDJVLCB-UHFFFAOYSA-N

物化性质

• 沸点：
  552.6±50.0 °C(predicted)
• 密度：
  1.467±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  羟甲香豆素 、 4-氯苯甲醛 在 哌啶 作用下， 反应 3.0h， 以65%的产率得到4-[2-(4-chlorophenyl)ethenyl]-7-hydroxychromen-2-one
  参考文献：
  名称：

  Stereospecificity of Diels–Alder Reactions Validated Using Ab Initio Calculations: Synthesis of Novel Coumarin and Phenanthridine Derivatives

  摘要：

  A new series of coumarin derivatives (2-5) was synthesized by reaction of phenylsulfonylacetonitrile (1) with 2-hydroxy-1-naphthaldehyde and/or salicyaldehyde. Compounds 3 and 5 were converted to the corresponding phenanthridine analogs 6 and 7, respectively. Compound 9a was treated with different dienophiles to furnish the endo adducts of compounds (11a-d) rather than the exo adducts. Ab initio calculations at the Hartree-Fock (HF) level using the basis set 6-31G (d,p) was used to study and validate the stereospecificity of compounds 11a-d and showed clearly that the endo adducts were thermodynamically favorable. PM3 parameters also showed that the endo adducts are thermodynamically and kinetically favorable. Tetrahydrobenzochromenone (11) was synthesized and allowed to react with different aromatic diazonium salts to give the corresponding 4-arylazo derivatives (13), which were converted to the corresponding diazaindenophenanthrene derivatives (14) by reaction with o-diamines.

  DOI：

  10.1080/00397910802711326