N-phenyl 3-(phenylsulfinyl)maleimide | 153615-76-0

• 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: N-phenyl 3-(phenylsulfinyl)maleimide
• 英文别名: N-phenyl-2-(phenylsulphinyl)maleimide；3-(Benzenesulfinyl)-1-phenylpyrrole-2,5-dione
• CAS: 153615-76-0
• 化学式: C₁₆H₁₁NO₃S
• 分子量: 297.334
• InChiKey: YURAGAMCVYWMEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 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：
  73.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-phenyl 3-(phenylsulfinyl)maleimide 在 盐酸 、 对苯二酚 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 4-hydroxy-7-phenyl-1-oxa-7-aza-as-indacene-6,8-dione
  参考文献：
  名称：

  Site Selectivity of the Diels−Alder Reactions of 3-[1-(tert-Butyldimethylsilyloxy)vin-1-yl]furan and 3-(Propen-2-yl)furan. Synthesis of 4-Substituted Benzofurans

  摘要：

  The Diels-Alder reaction of 5-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.

  DOI：

  10.1021/jo951546k
• 作为产物：
  描述：

  1-phenyl-3-(phenylthio)pyrrolidine-2,5-dione 在 N-氯代丁二酰亚胺 、 间氯过氧苯甲酸 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 12.17h， 生成 N-phenyl 3-(phenylsulfinyl)maleimide
  参考文献：
  名称：

  On the [42]Cycloaddition Approach to Indolo[2,3-a]carbazoles

  摘要：

  2,2'-Biindolyl 9 reacts with electron-deficient dienophiles at 100-110 degrees C to give low to moderate yields of Michael addition and formal [4 + 2] cycloaddition products, with the former predominant; the products derived from 9 and 2-(phenylsulphinyl)maleimides 14 and 15 undergo in situ elimination of benzenesulphenic acid, leading to 2,2'-biindolyl-substituted maleimides which can be efficiently photocyclised into indolo[2,3-a]carbazoles.

  DOI：

  10.1016/0040-4020(95)00735-q

文献信息

• On the [4 + 2] cycloaddition approach to indolo[2,3-a]carbazoles
  作者：John F. Barry、Timothy W. Wallace、Nigel D.A. Walshe

  DOI：10.1016/s0040-4039(00)73988-8

  日期：1993.8

  2,2'-Biindolyl 4 reacts with electron-deficient dienophiles at 100-110-degrees-C to give low to moderate yields of Michael addition and formal [4 + 2] cycloaddition products, with the former predominant; the products derived from 4 and 2-(phenylsulphinyl)maleimides 7 and 8 undergo in situ elimination of benzenesulphenic acid, leading to 2,2'-biindolyl-substituted maleimides which can be efficiently photocyclised into indolo[2,3-a]carbazoles.
• Site Selectivity of the Diels−Alder Reactions of 3-[1-(<i>tert</i>-Butyldimethylsilyloxy)vin-1-yl]furan and 3-(Propen-2-yl)furan. Synthesis of 4-Substituted Benzofurans
  作者：Aída Benítez、F. Ruth Herrera、Margarita Romero、Francisco X. Talamás、Joseph M. Muchowski

  DOI：10.1021/jo951546k

  日期：1996.1.1

  The Diels-Alder reaction of 5-vinylfurans 5 and 27 with DMAD, N-phenylmaleimide, and dimethyl maleate afforded products derived both from addition to the furan ring diene system (intraannular addition) and to the furan 2,3-double bond 3-vinyl group diene system (extraannular addition). For example, compounds 6 and 7 were obtained from 5 and DMAD. In contrast, dienophiles containing a phenylsulfinyl group, such as 19-21, gave products derived exclusively from the extraannular reaction mode. These products are useful precursors of 4-substituted benzofurans, especially 4-hydroxybenzofurans.
• On the [42]Cycloaddition Approach to Indolo[2,3-a]carbazoles
  作者：John F. Barry、Timothy W. Wallace、Nigel D.A. Walshe

  DOI：10.1016/0040-4020(95)00735-q

  日期：1995.11

  2,2'-Biindolyl 9 reacts with electron-deficient dienophiles at 100-110 degrees C to give low to moderate yields of Michael addition and formal [4 + 2] cycloaddition products, with the former predominant; the products derived from 9 and 2-(phenylsulphinyl)maleimides 14 and 15 undergo in situ elimination of benzenesulphenic acid, leading to 2,2'-biindolyl-substituted maleimides which can be efficiently photocyclised into indolo[2,3-a]carbazoles.