3-phenylmercapto-2-chloro-4,4-ethylenedioxycyclopent-2-en-1-one | 677308-56-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-phenylmercapto-2-chloro-4,4-ethylenedioxycyclopent-2-en-1-one
• 英文别名: 2-chloro-4,4-ethylenedioxy-3-phenylsulfanyl-2-cyclopentenone；1,4-Dioxaspiro[4.4]non-8-en-7-one, 8-chloro-9-(phenylthio)-；8-chloro-9-phenylsulfanyl-1,4-dioxaspiro[4.4]non-8-en-7-one
• CAS: 677308-56-4
• 化学式: C₁₃H₁₁ClO₃S
• 分子量: 282.748
• InChiKey: UFXRJFDWEMMQRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenylmercapto-2-chloro-4,4-ethylenedioxycyclopent-2-en-1-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以72%的产率得到2-chloro-4,4-ethylenedioxy-3-phenylsulfonylcyclopent-2-en-1-one
  参考文献：
  名称：

  Prostanoids: LXXXVII. Synthesis of 3-Hydroxy-2-phenylsulfonyl-2-cyclopentenone and Its Ethylene Acetal

  摘要：

  By oxidation of 3-phenylmercapto-2-chloro-4,4-ethylenedioxycyclopet-2-en-1-one with H2O2 in AcOH (or with m-ClC6H4CO3H in CH2Cl2) was obtained 2-chloro-3-phenylsulfonyl-4,4-ethylenedioxycyclopent-2-en-1-one which on reduction with NaBH4 or LiAlH4 afforded respectively 3-hydroxy-2-phenyl-sulfonylcyclopent-2-en-1-one and its ethyleneketal.

  DOI：

  10.1023/b:rujo.0000013142.41402.19
• 作为产物：
  描述：

  苯硫酚 、 8,9-二氯-1,4-二氧杂螺[4.4]壬-8-烯-7-酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到3-phenylmercapto-2-chloro-4,4-ethylenedioxycyclopent-2-en-1-one
  参考文献：
  名称：

  Prostanoids: LXXXVI. Synthesis and Reductive Transformations of 2-Chloro-4,4-ethylenedioxy-3-phenylsulfanyl-2-cyclopentenone

  摘要：

  The reduction of 2-chloro-4,4-ethylenedioxy-3-phenylsulfanyl-2-cyclopentenone with sodium tetrahydridoborate in ethanol yields 3-chloro-4-hydroxy-2-phenyisulfanyl-2-cyclopentenone, while with the use of lithium aluminum hydride in tetrahydrofuran or the system Zn/NH4Cl in methanol products of more profound reduction are obtained.

  DOI：

  10.1023/b:rujo.0000010567.22691.a5

文献信息

• Prostanoids: LXXXVI. Synthesis and Reductive Transformations of 2-Chloro-4,4-ethylenedioxy-3-phenylsulfanyl-2-cyclopentenone
  作者：N. A. Ivanova、A. A. Khusainova、F. G. Shangiraeva、R. R. Akhmetvaleev、M. S. Miftakhov

  DOI：10.1023/b:rujo.0000010567.22691.a5

  日期：2003.10

  The reduction of 2-chloro-4,4-ethylenedioxy-3-phenylsulfanyl-2-cyclopentenone with sodium tetrahydridoborate in ethanol yields 3-chloro-4-hydroxy-2-phenyisulfanyl-2-cyclopentenone, while with the use of lithium aluminum hydride in tetrahydrofuran or the system Zn/NH4Cl in methanol products of more profound reduction are obtained.
• Prostanoids: LXXXVII. Synthesis of 3-Hydroxy-2-phenylsulfonyl-2-cyclopentenone and Its Ethylene Acetal
  作者：N. A. Ivanova、F. G. Shangiraeva、M. S. Miftakhov

  DOI：10.1023/b:rujo.0000013142.41402.19

  日期：2003.11

  By oxidation of 3-phenylmercapto-2-chloro-4,4-ethylenedioxycyclopet-2-en-1-one with H2O2 in AcOH (or with m-ClC6H4CO3H in CH2Cl2) was obtained 2-chloro-3-phenylsulfonyl-4,4-ethylenedioxycyclopent-2-en-1-one which on reduction with NaBH4 or LiAlH4 afforded respectively 3-hydroxy-2-phenyl-sulfonylcyclopent-2-en-1-one and its ethyleneketal.