3-benzoyl-2,3-dihydro-2-benzothiazolecarbonitrile | 95479-51-9

• 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: 3-benzoyl-2,3-dihydro-2-benzothiazolecarbonitrile
• 英文别名: 2-Cyano-3-benzoyl-2,3-dihydrobenzothiazole；NSC-378663；3-benzoyl-2H-1,3-benzothiazole-2-carbonitrile
• CAS: 95479-51-9
• 化学式: C₁₅H₁₀N₂OS
• 分子量: 266.323
• InChiKey: ROWVQNNXSKEBKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-2,3-dihydro-2-benzothiazolecarbonitrile 、 1-氯-4-(碘甲基)苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 3.0h， 以100%的产率得到2-Cyano-2-(p-chlorobenzyl)-3-benzoyl-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
• 作为产物：
  描述：

  2-cyano-2,3-dihydro-3-methoxycarbonylbenzothiazole 在 sodium hydroxide 、 三氯化铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 87.0h， 生成 3-benzoyl-2,3-dihydro-2-benzothiazolecarbonitrile
  参考文献：
  名称：

  Uff, Barrie C.; Ho, Yee-Ping; Brown, David S., Journal of Chemical Research, Miniprint, 1989, # 11, p. 2652 - 2681

  摘要：

  DOI：

文献信息

• Reissert compound formation with five-membered ring heterocycles using trimethylsilyl cyanide
  作者：Barrie C. Uff、S. L. Anne、A. Chen、Yee-Ping Ho、Frank D. Popp、Joydeep Kant

  DOI：10.1039/c39840001245

  日期：——

  benzothiazole with trimethylsilyl cyanide and an acid chloride in CH2Cl2 gives the N-acyl-2-cyano-2,3-dihydrobenzothiazole in good yield; benzoxazole similarly is converted into a five-membered ring Reissert compound, providing the first examples in these series.

  在CH 2 Cl 2中用三甲基甲硅烷基氰化物和酰氯处理苯并噻唑，得到的N-酰基-2-氰基-2,3-二氢苯并噻唑具有良好的收率。苯并恶唑类似地被转化为五元环的Reissert化合物，提供了这些系列中的第一个实例。
• UFF, B. C.;CHEN, S. L. A. A.;HO, YEE-PING;POPP, F. D.;KANT, JOYDEEP, J. CHEM. SOC. CHEM. COMMUN., 1984, N 18, 1245-1246
  作者：UFF, B. C.、CHEN, S. L. A. A.、HO, YEE-PING、POPP, F. D.、KANT, JOYDEEP

  DOI：——

  日期：——
• Uff, Barrie C.; Ho, Yee-Ping; Brown, David S., Journal of Chemical Research, Miniprint, 1989, # 11, p. 2652 - 2681
  作者：Uff, Barrie C.、Ho, Yee-Ping、Brown, David S.、Fisher, Ian、Popp, Frank D.、Kant, Joydeep

  DOI：——

  日期：——
• 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.