8a-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-7-phenyl-5,5a,8a,8b-tetrahydro-furo[2,3-e]isoindole-6,8-dione | 174676-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 8a-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-7-phenyl-5,5a,8a,8b-tetrahydro-furo[2,3-e]isoindole-6,8-dione
• 英文别名: 8a-(benzenesulfinyl)-4-[tert-butyl(dimethyl)silyl]oxy-7-phenyl-5a,8b-dihydro-5H-furo[2,3-e]isoindole-6,8-dione
• CAS: 174676-68-7
• 化学式: C₂₈H₃₁NO₅SSi
• 分子量: 521.709
• InChiKey: DMSLSUDDQCYSCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8a-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-7-phenyl-5,5a,8a,8b-tetrahydro-furo[2,3-e]isoindole-6,8-dione 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以60%的产率得到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：

  α-(phenylthio)maleic anhydride 在 sodium acetate 、 乙酸酐 、 对苯二酚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 26.5h， 生成 8a-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-7-phenyl-5,5a,8a,8b-tetrahydro-furo[2,3-e]isoindole-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

文献信息

• 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.