2-(methoxy(phenyl)methyl)-3-methylbenzo[b]thiophene | 1334400-90-6

• 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-(methoxy(phenyl)methyl)-3-methylbenzo[b]thiophene
• 英文别名: 2-[Methoxy(phenyl)methyl]-3-methyl-1-benzothiophene
• CAS: 1334400-90-6
• 化学式: C₁₇H₁₆OS
• 分子量: 268.379
• InChiKey: RTCHNTQUDJKRDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  苯乙炔 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 10.0h， 生成 2-(methoxy(phenyl)methyl)-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

• Multicomponent Synthesis of Benzothiophen‐2‐acetic Esters by a Palladium Iodide Catalyzed <i>S</i> ‐cyclization – Alkoxycarbonylation Sequence
  作者：Raffaella Mancuso、Melania Lettieri、Ida Ziccarelli、Patrizio Russo、Antonio Palumbo Piccionello、Bartolo Gabriele

  DOI：10.1002/adsc.202100782

  日期：2021.10.5

  S-cyclization-demethylation-alkoxycarbonylation-reduction sequence promoted by the PdI2/KI catalytic system, occurring under relatively mild conditions (40 atm, 80 °C, 15 h). Benzothiophene-2-acetic esters are obtained in moderate to good yields (35–70%) starting from variously substituted substrates in combination with different alcohols as external nucleophiles (17 examples).

  介绍了一种从简单的结构单元 [1-(2-(甲硫基) 苯基)prop-2-yn-1-ols、一氧化碳和醇)] 多组分合成苯并噻吩衍生物的催化羰基化方法。它基于PdI 2 /KI 催化系统促进的S -环化 - 去甲基化 - 烷氧基羰基化 - 还原序列，发生在相对温和的条件下（40 个大气压，80°C，15 小时）。苯并噻吩-2-乙酸酯以中等至良好的产率（35-70%）从各种取代的底物与作为外部亲核试剂的不同醇开始（17 个例子）获得。
• 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.