(E)-4-(benzo[b]thiophen-3-yl)-1-phenylbut-2-en-1-one | 1612794-58-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (E)-4-(benzo[b]thiophen-3-yl)-1-phenylbut-2-en-1-one
• 英文别名: (E)-4-(1-benzothiophen-3-yl)-1-phenylbut-2-en-1-one
• CAS: 1612794-58-7
• 化学式: C₁₈H₁₄OS
• 分子量: 278.375
• InChiKey: BZCDXSRYJQYOIK-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(benzo[b]thiophen-3-yl)-1-phenylbut-2-en-1-one 、 N-(4-溴苯基)马来酰亚胺 在 奎宁胺 、 水杨酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以88%的产率得到
  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
• 作为产物：
  描述：

  3-甲醛苯并噻吩 在 sodium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.0h， 生成 (E)-4-(benzo[b]thiophen-3-yl)-1-phenylbut-2-en-1-one
  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.