3-Hydroxy-2-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one | 150111-61-8

• 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: 3-Hydroxy-2-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one
• 英文别名: 2-(Benzenesulfonylmethyl)-3-hydroxycyclopent-2-en-1-one；2-(benzenesulfonylmethyl)-3-hydroxycyclopent-2-en-1-one
• CAS: 150111-61-8
• 化学式: C₁₂H₁₂O₄S
• 分子量: 252.291
• InChiKey: XAQBCSBNUOYAKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-2-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one 在 双(乙腈)氯化钯(II) 三乙胺 、 lithium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3-((E)-3-Hydroxy-oct-1-enyl)-2-phenylsulfanylmethyl-cyclopent-2-enone
  参考文献：
  名称：

  Synthesis of PGB1 analogs by radical chain substitution reaction

  摘要：

  PGB1 analogues with functionalized or sulfur atom-containing alpha-side chains have been synthesized in several steps from 1,3-cyclopentanedione. Introduction of alpha- and omega-side chains into the PGB1 cyclopentenone skeleton has been accomplished by replacement of an allylic sulfonyl group in 3-substituted 2-[(phenylsulfonyl)methyl]-2-cyclopenten-1-one by stabilized carbanions or thiolate ions and Pd(0)-catalyzed cross-coupling reaction between the vinylic iodide moiety in 2-substituted 3-iodo-2-cyclopenten-1-ones and a vinyltin reagent or an alkyne, respectively. The former substitution reaction with stabilized carbanions has been confirmed to proceed via a radical chain mechanism of S(RN)1 type by investigating the effects of a radical scavenger and by the ESR studies. Further, comparison of the reduction potentials of substrates with those of products supports a single electron transfer mechanism.

  DOI：

  10.1021/jo00067a030
• 作为产物：
  描述：

  聚合甲醛 、 1,3-环戊二酮 、 sodium benzenesulfonate 在 溶剂黄146 作用下， 反应 5.0h， 以86%的产率得到3-Hydroxy-2-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one
  参考文献：
  名称：

  Synthesis of PGB1 analogs by radical chain substitution reaction

  摘要：

  PGB1 analogues with functionalized or sulfur atom-containing alpha-side chains have been synthesized in several steps from 1,3-cyclopentanedione. Introduction of alpha- and omega-side chains into the PGB1 cyclopentenone skeleton has been accomplished by replacement of an allylic sulfonyl group in 3-substituted 2-[(phenylsulfonyl)methyl]-2-cyclopenten-1-one by stabilized carbanions or thiolate ions and Pd(0)-catalyzed cross-coupling reaction between the vinylic iodide moiety in 2-substituted 3-iodo-2-cyclopenten-1-ones and a vinyltin reagent or an alkyne, respectively. The former substitution reaction with stabilized carbanions has been confirmed to proceed via a radical chain mechanism of S(RN)1 type by investigating the effects of a radical scavenger and by the ESR studies. Further, comparison of the reduction potentials of substrates with those of products supports a single electron transfer mechanism.

  DOI：

  10.1021/jo00067a030

文献信息

• Synthesis of PGB1 analogs by radical chain substitution reaction
  作者：Rui Tamura、Masatoshi Kohno、Sei Utsunomiya、Kunihiko Yamawaki、Nagao Azuma、Akira Matsumoto、Yasutaka Ishii

  DOI：10.1021/jo00067a030

  日期：1993.7

  PGB1 analogues with functionalized or sulfur atom-containing alpha-side chains have been synthesized in several steps from 1,3-cyclopentanedione. Introduction of alpha- and omega-side chains into the PGB1 cyclopentenone skeleton has been accomplished by replacement of an allylic sulfonyl group in 3-substituted 2-[(phenylsulfonyl)methyl]-2-cyclopenten-1-one by stabilized carbanions or thiolate ions and Pd(0)-catalyzed cross-coupling reaction between the vinylic iodide moiety in 2-substituted 3-iodo-2-cyclopenten-1-ones and a vinyltin reagent or an alkyne, respectively. The former substitution reaction with stabilized carbanions has been confirmed to proceed via a radical chain mechanism of S(RN)1 type by investigating the effects of a radical scavenger and by the ESR studies. Further, comparison of the reduction potentials of substrates with those of products supports a single electron transfer mechanism.