3-(Benzenesulfonyl)-1-phenylpyrrole-2,5-dione | 1312542-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-(Benzenesulfonyl)-1-phenylpyrrole-2,5-dione
• CAS: 1312542-01-0
• 化学式: C₁₆H₁₁NO₄S
• 分子量: 313.334
• InChiKey: PBCDSAYFLWUQIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(Benzenesulfonyl)-1-phenylpyrrole-2,5-dione 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 samarium diiodide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.33h， 生成 (1S,2S,3R,6S,8R,10S,11R)-11-[tert-butyl(dimethyl)silyl]oxy-3-methyl-5-phenyl-8-triethylsilyloxy-7-oxa-5-azatetracyclo[6.4.0.02,6.03,10]dodecan-4-one
  参考文献：
  名称：

  Controlling the Facial Selectivity of Asymmetric [4 + 2] Cyclo-additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B

  摘要：

  Reglo-, stereo-, and facial selective [4 + 2] cycloadditions between highly activated vinyl sulfones and 1,3-dienes derived from (R)-4-tert-wbutyldimethylsilyloxy-2-cyclohexen-1-one provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. This new methodology has been successfully applied to the asymmetric synthesis of the cis-decalin core structure of the potent anticancer marine natural products superstolides A and B.

  DOI：

  10.1021/ol201095b

文献信息

• Controlling the Facial Selectivity of Asymmetric [4 + 2] Cyclo-additions: A Concise Synthesis of the <i>cis</i>-Decalin Core Structure of Superstolides A and B
  作者：Lei Chen、Zhengmao Hua、Gangqin Li、Zhendong Jin

  DOI：10.1021/ol201095b

  日期：2011.7.15

  Reglo-, stereo-, and facial selective [4 + 2] cycloadditions between highly activated vinyl sulfones and 1,3-dienes derived from (R)-4-tert-wbutyldimethylsilyloxy-2-cyclohexen-1-one provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. This new methodology has been successfully applied to the asymmetric synthesis of the cis-decalin core structure of the potent anticancer marine natural products superstolides A and B.