3,5-dimethyl-4-ethoxybenzonitrile | 1396690-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-dimethyl-4-ethoxybenzonitrile
• 英文别名: 4-Ethoxy-3,5-dimethylbenzonitrile
• CAS: 1396690-71-3
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: SUCHZLQVXGIADC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙氧基-1,3-二甲基-苯 在 copper(II) nitrate trihydrate 、 碘 、 二氧化氮 作用下， 以 乙腈 为溶剂， 反应 30.0h， 生成 3,5-dimethyl-4-ethoxybenzonitrile
  参考文献：
  名称：

  氮氧化物催化的芳烃亲电碘化

  摘要：

  AbstractNitrogen dioxide is demonstrated to be an effective catalyst precursor for the iodination of alkoxy‐substituted benzenes and naphthalenes. Different from the transition metal catalysts, nitrogen dioxide can be easily separated from the final products, and is free of heavy metal waste. Although the present catalyst precursor is toxic, it does not stain the final products due to its low‐boiling character. No other reagents apart from 0.5 equiv. of iodine (I2), 6.5 mol% nitrogen dioxide and acetonitrile solvent were used in the iodination, and basically all the iodine atoms in the iodine source were transferred to the iodination products, showing that the presented protocol is highly atom‐economic and practical.magnified image

  DOI：

  10.1002/adsc.201300581

文献信息

• Selective para-Cyanation of Alkoxy- and Benzyloxy-Substituted Benzenes with Potassium Ferricyanide Promoted by Copper(II) Nitrate and Iodine
  作者：Yunlai Ren、Mengjie Yan、Shuang Zhao、Jianji Wang、Junying Ma、Xinzhe Tian、Weiping Yin

  DOI：10.1002/adsc.201200235

  日期：2012.8.13

  A simple method was developed for selective para-cyanation of alkoxy- and benzyloxy-substituted benzenes with 0.5 equivalents of potassium ferricyanide, 0.8 equivalants of copper(II) nitrate and 0.5 equivalents of iodine in acetonitrile. Among various phenyl carbon-hydrogen bonds, those at the para-position with regard to the alkoxy or benzyloxy groups were selectively cyanated in 20% to 87% yields

  一个简单的方法，用于选择性地开发对用0.5当量的铁氰化钾，硝酸铜0.8 equivalants和在乙腈中的0.5当量的碘的烷氧基和苄氧基-取代的苯的-cyanation。在各种苯基碳氢键中，相对于烷氧基或苄氧基处于对位的那些被选择性氰化，产率为20％至87％（23个例子）。本方法使用可商购的试剂，并且可以以十克规模进行。有趣的是，在不存在铁氰化钾的情况下，甲氧基苯以32％的产率氰化，这表明一部分产品的腈基可能来自溶剂乙腈。
• US7622490B2
  申请人：——

  公开号：US7622490B2

  公开（公告）日：2009-11-24
• US7659404B2
  申请人：——

  公开号：US7659404B2

  公开（公告）日：2010-02-09
• Nitrogen Dioxide-Catalyzed Electrophilic Iodination of Arenes
  作者：Yun-Lai Ren、Huantao Shang、Jianji Wang、Xinzhe Tian、Shuang Zhao、Qian Wang、Fuwei Li

  DOI：10.1002/adsc.201300581

  日期：2013.11.25

  AbstractNitrogen dioxide is demonstrated to be an effective catalyst precursor for the iodination of alkoxy‐substituted benzenes and naphthalenes. Different from the transition metal catalysts, nitrogen dioxide can be easily separated from the final products, and is free of heavy metal waste. Although the present catalyst precursor is toxic, it does not stain the final products due to its low‐boiling character. No other reagents apart from 0.5 equiv. of iodine (I2), 6.5 mol% nitrogen dioxide and acetonitrile solvent were used in the iodination, and basically all the iodine atoms in the iodine source were transferred to the iodination products, showing that the presented protocol is highly atom‐economic and practical.magnified image