2-Cyano-2-methyl-3-o-toluoyl-2,3-dihydrobenzothiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-Cyano-2-methyl-3-o-toluoyl-2,3-dihydrobenzothiazole
• 英文别名: 2-Methyl-3-(2-methylbenzoyl)-1,3-benzothiazole-2-carbonitrile
• 化学式: C₁₇H₁₄N₂OS
• 分子量: 294.377
• InChiKey: LAJOOUUDQNIVNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻甲基苯甲酰氯 在 三氯化铝 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 3.0h， 生成 2-Cyano-2-methyl-3-o-toluoyl-2,3-dihydrobenzothiazole
  参考文献：
  名称：

  Synthesis and stereochemistry of Reissert compounds from benzothiazole

  摘要：

  Benzothiazole Reissert compounds 1-5 were synthesized, characterized and alkylated to produce 6-9. Conformational analysis of 2 by the use of high resolution (400 MHz) variable temperature NMR spectroscopy indicated that the Z to E amide conformer ratio is 79:21 (+/-3%) in CDCl3 at 213 K (-60-degrees-C) and 57:43 (+/-3%) in C6D5CD3 at 213 K. Aromatic solvent induced shifts were employed to determine the distribution of rotamers and indicated that the alkylated benzothiazole Reissert compound 8 existed in only the Z amide conformation. Hindered aryl-carbonyl rotation was also detected in the Reissert compounds.

  DOI：

  10.1021/jo00062a032

文献信息

• Synthesis and stereochemistry of Reissert compounds from benzothiazole
  作者：Ashish Pandya、Harry W. Gibson

  DOI：10.1021/jo00062a032

  日期：1993.5

  Benzothiazole Reissert compounds 1-5 were synthesized, characterized and alkylated to produce 6-9. Conformational analysis of 2 by the use of high resolution (400 MHz) variable temperature NMR spectroscopy indicated that the Z to E amide conformer ratio is 79:21 (+/-3%) in CDCl3 at 213 K (-60-degrees-C) and 57:43 (+/-3%) in C6D5CD3 at 213 K. Aromatic solvent induced shifts were employed to determine the distribution of rotamers and indicated that the alkylated benzothiazole Reissert compound 8 existed in only the Z amide conformation. Hindered aryl-carbonyl rotation was also detected in the Reissert compounds.