2-imino-3-phenylsulfonylbenzo[f]chromene | 7605-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-imino-3-phenylsulfonylbenzo[f]chromene
• 英文别名: 2-Benzolsulfonyl-benzochromen-3-imin；2-Benzolsulfonyl-benzo[f]chromen-3-imin；2-(Benzenesulfonyl)benzo[f]chromen-3-imine
• CAS: 7605-49-4
• 化学式: C₁₉H₁₃NO₃S
• 分子量: 335.383
• InChiKey: PCLOPQBTLGVJHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-imino-3-phenylsulfonylbenzo[f]chromene 在 盐酸 作用下， 以 乙醇 为溶剂， 以98%的产率得到3-phenylsulfonyl-2H-benzo[f]-2-chromenone
  参考文献：
  名称：

  Utility of Sulphones in Heterocyclic Synthesis: Synthesis of Some Pyridine, Chromene and Thiophene Derivatives

  摘要：

  当苯磺酰乙腈（1）与α,β-不饱和腈（2a,b）和/或 2-羟基萘反应时，可分别生成吡啶衍生物（3a,b）和/或亚氨基苯并吡喃衍生物（4）。我们还研究了 (1) 对一些 a 卤代化合物的作用。

  DOI：

  10.3390/50500701
• 作为产物：
  描述：

  苯磺酰乙腈 、 2-羟基-1-萘甲醛 在 TEA 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到2-imino-3-phenylsulfonylbenzo[f]chromene
  参考文献：
  名称：

  Utility of Sulphones in Heterocyclic Synthesis: Synthesis of Some Pyridine, Chromene and Thiophene Derivatives

  摘要：

  当苯磺酰乙腈（1）与α,β-不饱和腈（2a,b）和/或 2-羟基萘反应时，可分别生成吡啶衍生物（3a,b）和/或亚氨基苯并吡喃衍生物（4）。我们还研究了 (1) 对一些 a 卤代化合物的作用。

  DOI：

  10.3390/50500701

文献信息

• Utility of Sulphones in Heterocyclic Synthesis: Synthesis of Some Pyridine, Chromene and Thiophene Derivatives
  作者：A. Fadda、Hala Refat、M. Zaki

  DOI：10.3390/50500701

  日期：——

  Phenylsulfonylacetonitrile (1) when reacted with α,β-unsaturated nitriles (2a,b) and/or 2-hydroxynaphthaldehyde yields pyridine derivatives (3a,b) and / or the iminochromene derivative (4) respectively. The behavior of (1) towards some a-halogenated compounds has been investigated.

  当苯磺酰乙腈（1）与α,β-不饱和腈（2a,b）和/或 2-羟基萘反应时，可分别生成吡啶衍生物（3a,b）和/或亚氨基苯并吡喃衍生物（4）。我们还研究了 (1) 对一些 a 卤代化合物的作用。
• Stereospecificity of Diels–Alder Reactions Validated Using Ab Initio Calculations: Synthesis of Novel Coumarin and Phenanthridine Derivatives
  作者：A. El-Shafei、A. A. Fadda、I. I. Abdel-Gawad、E. H. E. Youssif

  DOI：10.1080/00397910802711326

  日期：2009.7.21

  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.