2-(ethoxyphenylmethyl)-3-methylbenzo[b]thiophene | 1334400-98-4

• 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: 2-(ethoxyphenylmethyl)-3-methylbenzo[b]thiophene
• 英文别名: 2-[Ethoxy(phenyl)methyl]-3-methyl-1-benzothiophene
• CAS: 1334400-98-4
• 化学式: C₁₈H₁₈OS
• 分子量: 282.406
• InChiKey: FGGSMYHZJCFWQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-疏基苯乙酮 在 溴乙烷 、 偶氮二异丁腈 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 17.0h， 生成 2-(ethoxyphenylmethyl)-3-methylbenzo[b]thiophene
  参考文献：
  名称：

  Synthesis of Benzothiophene Derivatives by Pd-Catalyzed or Radical-Promoted Heterocyclodehydration of 1-(2-Mercaptophenyl)-2-yn-1-ols

  摘要：

  Novel and convenient approaches to benzothiophene derivatives 3 and 5 have been developed, based on heterocyclization reactions of 1-(2-mercaptophenyl)-2-yn-1-is 2 or 4, respectively, readily available from alkynylation of 2-mercaptobenzaldehydes or 1-(2-mercaptophenyl) ketones 1. In particular, 1-(2-mercaptophenyl)-2-yn-1-ols 2, bearing a CH2R substituent on the triple bond (R = alkyl, aryl), were conveniently converted in fair to good yields (55-82%) into (E)-2-(1-alkenyl)benzothiophenes 3 when allowed to react in the presence of catalytic amounts (2 mol %) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10) at 80-100 degrees C in MeCN as the solvent, through a heterocyclodehydration process. On the other hand, 2-alkoxymethylbenzothiophenes 5 were selectively obtained in fair to excellent yields (49-98%) via a radical-promoted substitutive heterocyclodehydration process, by reacting 1-(2-mercaptophenyl)-2-yn-1-ols 4 (bearing an alkyl or aryl substituent on the triple bond) in alcoholic media at 80-100 degrees C in the presence of a radical initiator, such as AIBN.

  DOI：

  10.1021/jo201471k

文献信息

• Synthesis of Benzothiophene Derivatives by Pd-Catalyzed or Radical-Promoted Heterocyclodehydration of 1-(2-Mercaptophenyl)-2-yn-1-ols
  作者：Bartolo Gabriele、Raffaella Mancuso、Elvira Lupinacci、Lucia Veltri、Giuseppe Salerno、Carla Carfagna

  DOI：10.1021/jo201471k

  日期：2011.10.21

  Novel and convenient approaches to benzothiophene derivatives 3 and 5 have been developed, based on heterocyclization reactions of 1-(2-mercaptophenyl)-2-yn-1-is 2 or 4, respectively, readily available from alkynylation of 2-mercaptobenzaldehydes or 1-(2-mercaptophenyl) ketones 1. In particular, 1-(2-mercaptophenyl)-2-yn-1-ols 2, bearing a CH2R substituent on the triple bond (R = alkyl, aryl), were conveniently converted in fair to good yields (55-82%) into (E)-2-(1-alkenyl)benzothiophenes 3 when allowed to react in the presence of catalytic amounts (2 mol %) of PdI2 in conjunction with KI (KI:PdI2 molar ratio = 10) at 80-100 degrees C in MeCN as the solvent, through a heterocyclodehydration process. On the other hand, 2-alkoxymethylbenzothiophenes 5 were selectively obtained in fair to excellent yields (49-98%) via a radical-promoted substitutive heterocyclodehydration process, by reacting 1-(2-mercaptophenyl)-2-yn-1-ols 4 (bearing an alkyl or aryl substituent on the triple bond) in alcoholic media at 80-100 degrees C in the presence of a radical initiator, such as AIBN.