2-[(4-chlorophenyl)(phenylthio)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone | 1609076-47-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-[(4-chlorophenyl)(phenylthio)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone
• 英文别名: 2-[(4-Chlorophenyl)-phenylsulfanylmethyl]-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one
• CAS: 1609076-47-2
• 化学式: C₂₁H₂₁ClO₂S
• 分子量: 372.916
• InChiKey: BSPQDOVKKUCUGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  安替比林 、 2-[(4-chlorophenyl)(phenylthio)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone 在 manganese(II) chloride tetrahydrate 作用下， 以 硝基甲烷 为溶剂， 反应 6.0h， 以93%的产率得到4-[(4-chlorophenyl)(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
  参考文献：
  名称：

  芳香醛与两种不同亲核试剂的三组分反应及其离解能力的下游转化率决定

  摘要：

  AbstractMany three‐component reactions of aromatic aldehydes with activated methylene derivatives and an associated nucleophile have been developed by using L‐proline as the catalyst. Nucleophiles, such as indoles, thiophenols, mercaptans, 2‐methylfuran and benzenesulfinic acid, could be successfully used in the reactions while the activated methylene derivatives can be 1,3‐cyclohexanedione, dimedone, 1,3‐cyclopentanedione, 1‐phenyl‐3‐methyl‐5‐pyrazolone, 4‐hydroxycoumarin, 4,6‐dihydroxy‐2‐mercaptopyrimidine, 4‐hydroxy‐1‐methyl‐2quinolone, 4‐hydroxy‐6‐methyl‐2‐pyrone and 2‐hydroxy‐1,4‐naphthoquinone. Investigation of the downstream utilization of the products from the above multicomponent reactions (MCRs) revealed that selective cleavages of carbon‐carbon and carbon‐heteroatom bonds in these molecules are indeed possible, which opens an avenue to access some new SN1‐type reactions. Particularly, when the MCR product of an aromatic aldehyde, dimedone and thiophenol was treated with an acid catalyst in the presence of an appropriate nucleophile, cleavage of the carbon‐sulfur bond occurred preferentially, thus providing many complex molecules that cannot be attained by other known methods.magnified image

  DOI：

  10.1002/adsc.201300790
• 作为产物：
  描述：

  4-氯苯甲醛 、 5,5-二甲基-1,3-环己二酮 、 苯硫酚 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以99%的产率得到2-[(4-chlorophenyl)(phenylthio)methyl]-3-hydroxy-5,5-dimethylcyclohex-2-enone
  参考文献：
  名称：

  芳香醛与两种不同亲核试剂的三组分反应及其离解能力的下游转化率决定

  摘要：

  AbstractMany three‐component reactions of aromatic aldehydes with activated methylene derivatives and an associated nucleophile have been developed by using L‐proline as the catalyst. Nucleophiles, such as indoles, thiophenols, mercaptans, 2‐methylfuran and benzenesulfinic acid, could be successfully used in the reactions while the activated methylene derivatives can be 1,3‐cyclohexanedione, dimedone, 1,3‐cyclopentanedione, 1‐phenyl‐3‐methyl‐5‐pyrazolone, 4‐hydroxycoumarin, 4,6‐dihydroxy‐2‐mercaptopyrimidine, 4‐hydroxy‐1‐methyl‐2quinolone, 4‐hydroxy‐6‐methyl‐2‐pyrone and 2‐hydroxy‐1,4‐naphthoquinone. Investigation of the downstream utilization of the products from the above multicomponent reactions (MCRs) revealed that selective cleavages of carbon‐carbon and carbon‐heteroatom bonds in these molecules are indeed possible, which opens an avenue to access some new SN1‐type reactions. Particularly, when the MCR product of an aromatic aldehyde, dimedone and thiophenol was treated with an acid catalyst in the presence of an appropriate nucleophile, cleavage of the carbon‐sulfur bond occurred preferentially, thus providing many complex molecules that cannot be attained by other known methods.magnified image

  DOI：

  10.1002/adsc.201300790