2-methylbenzo[b]thiophene-3-carbonitrile | 39812-03-8

• 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-methylbenzo[b]thiophene-3-carbonitrile
• 英文别名: 2-methyl-1-benzothiophene-3-carbonitrile
• CAS: 39812-03-8
• 化学式: C₁₀H₇NS
• 分子量: 173.238
• InChiKey: WJNWOPKEOZRMPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-cyano-2H-1-benzothiopyran 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.33h， 以25%的产率得到2-methylbenzo[b]thiophene-3-carbonitrile
  参考文献：
  名称：

  The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide

  摘要：

  Two different roles of sodium azide under two different conditions are described here along with the plausible mechanisms. When sodium azide was treated with cyanochromenes under catalyst free conditions, the azide anion acted as a base. Hence, a base mediated rearrangement of cyanochromenes was resulted in formation of benzofuran derivatives. However, in the presence of catalytic amount of CuI the azide anion acted as a diene to produce chromenotetrazoles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.062

文献信息

• Yoshida, Kunihisa; Miyoshi, Kohji, Journal of the Chemical Society. Perkin transactions I, 1992, # 3, p. 333 - 336
  作者：Yoshida, Kunihisa、Miyoshi, Kohji

  DOI：——

  日期：——
• US7915280B2
  申请人：——

  公开号：US7915280B2

  公开（公告）日：2011-03-29
• The study of catalyst free and copper catalyzed reactions of cyanochromenes and sodium azide
  作者：Sachin D. Gawande、Mustafa J. Raihan、Manoj R. Zanwar、Veerababurao Kavala、Donala Janreddy、Chun-Wei Kuo、Mei-Ling Chen、Ting-Shen Kuo、Ching-Fa Yao

  DOI：10.1016/j.tet.2012.12.062

  日期：2013.2

  Two different roles of sodium azide under two different conditions are described here along with the plausible mechanisms. When sodium azide was treated with cyanochromenes under catalyst free conditions, the azide anion acted as a base. Hence, a base mediated rearrangement of cyanochromenes was resulted in formation of benzofuran derivatives. However, in the presence of catalytic amount of CuI the azide anion acted as a diene to produce chromenotetrazoles. (C) 2013 Elsevier Ltd. All rights reserved.