(3aS,4S,10aS,10bR)-2-(4-bromophenyl)-4-(2-phenyl-2-thioxoethyl)-3a,4,10a,10b-tetrahydro-1H-benzo[4,5]thieno[2,3-e]isoindole-1,3(2H)-dione | 1612794-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,10aS,10bR)-2-(4-bromophenyl)-4-(2-phenyl-2-thioxoethyl)-3a,4,10a,10b-tetrahydro-1H-benzo[4,5]thieno[2,3-e]isoindole-1,3(2H)-dione
• 英文别名: (3aS,4S,10aS,10bR)-2-(4-bromophenyl)-4-phenacyl-3a,4,10a,10b-tetrahydro-[1]benzothiolo[2,3-e]isoindole-1,3-dione
• CAS: 1612794-68-9
• 化学式: C₂₈H₂₀BrNO₃S
• 分子量: 530.442
• InChiKey: AHIGLYQTOHEGEZ-VDKXGUEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲醛苯并噻吩 在 奎宁胺 、 sodium 、 水杨酸 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 34.0h， 生成 (3aS,4S,10aS,10bR)-2-(4-bromophenyl)-4-(2-phenyl-2-thioxoethyl)-3a,4,10a,10b-tetrahydro-1H-benzo[4,5]thieno[2,3-e]isoindole-1,3(2H)-dione 、 2-(4-bromophenyl)-4-(2-phenyl-2-thioxoethyl)-3a,4,10a,10b-tetrahydro-1H-benzo[4,5]thieno[2,3-e]isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Asymmetric Dearomatic Diels–Alder Reactions of Diverse Heteroarenes via π-System Activation

  摘要：

  An asymmetric dearomatic Diels-Alder protocol for various heteroarenes, such as benzofuran, benzothiophene, or even furan, has been developed via pi-system activation. This method involves in situ generation of formal trienamine species embedding a heteroaromatic moiety, and an array of chiral fused frameworks with high molecular complexity and skeletal diversity were efficiently constructed in good to excellent stereoselectivity by the catalysis of a cinchona-based primary amine.

  DOI：

  10.1021/ol501217u

文献信息

• Asymmetric Dearomatic Diels–Alder Reactions of Diverse Heteroarenes via π-System Activation
  作者：You-Cai Xiao、Cai-Zhen Yue、Peng-Qiao Chen、Ying-Chun Chen

  DOI：10.1021/ol501217u

  日期：2014.6.20

  An asymmetric dearomatic Diels-Alder protocol for various heteroarenes, such as benzofuran, benzothiophene, or even furan, has been developed via pi-system activation. This method involves in situ generation of formal trienamine species embedding a heteroaromatic moiety, and an array of chiral fused frameworks with high molecular complexity and skeletal diversity were efficiently constructed in good to excellent stereoselectivity by the catalysis of a cinchona-based primary amine.