2-chloro-4,4-ethylenedioxy-3-phenylsulfonylcyclopent-2-en-1-one | 681270-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-chloro-4,4-ethylenedioxy-3-phenylsulfonylcyclopent-2-en-1-one
• 英文别名: 3-phenylsulfonyl-2-chloro-4,4-ethylenedioxycyclopent-2-en-1-one；2-Chloro-3-phenylsulfonyl-4,4-ethylenedioxycyclopent-2-en-1-one；9-(benzenesulfonyl)-8-chloro-1,4-dioxaspiro[4.4]non-8-en-7-one
• CAS: 681270-14-4
• 化学式: C₁₃H₁₁ClO₅S
• 分子量: 314.746
• InChiKey: NVRWAXCKAZOEAL-UHFFFAOYSA-N

物化性质

• 沸点：
  500.6±50.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 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：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-4,4-ethylenedioxy-3-phenylsulfonylcyclopent-2-en-1-one 在 sodium tetrahydroborate 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.33h， 以75%的产率得到4-hydroxy-2-phenylsulfonylcyclopent-2-en-1-ol
  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：

  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

文献信息

• New “sp 2 -bonded” carbanucleosides
  作者：N. A. Ivanova、A. G. Mustafin、F. G. Usmanova、S. P. Ivanov、M. S. Miftakhov

  DOI：10.1134/s1070428009020171

  日期：2009.2

  By reaction of 2,3-dichloro-, 2,3,5-trichloro-, 2,5-dichloro-3-phenylsulfonyl-, 2-chloro-3-phenylsulfonyl-4,4-ethylenedioxycyclopent-2-en-1-ones with uracyl 3- and 2-uracyl derivatives were obtained of the corresponding chlorocyclopentenone.
• Reactions of 2-Chloro-4,4-ethylenedioxy-3-phenylsulfonyl-cyclopent-2-en-1-one with some hydride reducing agents and carbon-centered nucleophiles
  作者：N. A. Ivanova、F. G. Usmanova、M. S. Miftakhov

  DOI：10.1134/s107042800709014x

  日期：2007.9

  2-Chloro-4,4-ethylenedioxy-3-phenylsulfonylcyclopent-2-en-1-one reacts with NaBH4 and LiAlH4 to give, depending on the conditions, 4,4-ethylenedioxy-2-chloro-3-phenylsulfonylcyclopent-2-en-1-ol and 4,4-ethylenedioxy-3-phenylsulfonylcyclopent-2-en-1-ol, as well as 4,4-ethylenedioxy-3-phenylsulfonylcyclopentan- 1-ol. Reactions of the title compound with diethyl malonate under basic conditions occurs at the double-bonded carbon atoms to form a couple of the addition-elimination products at C-2 and C-3.