3-acetyl-6-nitro-2H-thiochromene | 136489-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫色烯
• 英文名称: 3-acetyl-6-nitro-2H-thiochromene
• 英文别名: 1-(6-nitro-2H-thiochromen-3-yl)ethanone
• CAS: 136489-33-3
• 化学式: C₁₁H₉NO₃S
• 分子量: 235.263
• InChiKey: ZORMDOWAZLBDEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-Mercapto-5-nitro-benzaldehyd-tert-butylimin 、 丁烯酮 以 苯 为溶剂， 以85%的产率得到3-acetyl-6-nitro-2H-thiochromene
  参考文献：
  名称：

  Zur Synthese von 6-nitrosubstituierten 2H-Benzo[b]thiopyran-Derivaten aus 2-Mercapto-5-nitro-benzaldehyd

  摘要：

  Benzene derivatives useful as C3S-building blocks for the synthesis of 2H-benzo[b]thiopyrans are not easily available. The synthesis starting with 2-chloro-benzaldehyde via 2-chloro-5-nitro-benzaldehyde to 2-mercapto-5-nitro-benzaldehyde-tert-butylimin 1 b and its cyclisation to 2H-benzo[b]thiopyrans (2 a-h) and (3 a-d) is described. By reaction with acceptor substituted alkenes, e.g. acroleine or omega-nitrostyrene respectively 2-chloro-propenes, e.g. substituted beta-chloroacroleines or 2-chloro-propene-1,3-dicarboxylates the compounds 2 a-h and 3 a-d are obtained. Vilsmeier's reaction of the diester 3 d with DMF/POCl3 yields the formyl compound 4.

  DOI：

  10.1002/prac.19923340209

文献信息

• One-pot synthesis of 2<i>H</i>-thiochromenes<i>via</i>TiCl₄-promoted reaction of 2-<i>tert</i>-butylthiobenzaldehydes with activated alkenes
  作者：Chang Hoon Lee、Kee-Jung Lee

  DOI：10.1002/jhet.182

  日期：2009.9

  A facile synthesis of 2H-thiochromenes through TiCl4-promoted reaction of 2-tert-butylthiobenzaldehydes with activated alkenes is described. J. Heterocyclic Chem., (2009).

  描述了通过TiCl 4促进的2-叔丁基硫代苯甲醛与活化的烯烃的反应，轻松合成2 H-硫代色酮。J.杂环化​​学，（2009）。
• Zur Synthese von 6-nitrosubstituierten 2H-Benzo[b]thiopyran-Derivaten aus 2-Mercapto-5-nitro-benzaldehyd
  作者：M. Wei�enfels、M. Pulst、D. Greif

  DOI：10.1002/prac.19923340209

  日期：——

  Benzene derivatives useful as C3S-building blocks for the synthesis of 2H-benzo[b]thiopyrans are not easily available. The synthesis starting with 2-chloro-benzaldehyde via 2-chloro-5-nitro-benzaldehyde to 2-mercapto-5-nitro-benzaldehyde-tert-butylimin 1 b and its cyclisation to 2H-benzo[b]thiopyrans (2 a-h) and (3 a-d) is described. By reaction with acceptor substituted alkenes, e.g. acroleine or omega-nitrostyrene respectively 2-chloro-propenes, e.g. substituted beta-chloroacroleines or 2-chloro-propene-1,3-dicarboxylates the compounds 2 a-h and 3 a-d are obtained. Vilsmeier's reaction of the diester 3 d with DMF/POCl3 yields the formyl compound 4.