(7-bromo-2,3-dihydro-1,4-benzodioxin-6-yl)(thiophen-2-yl)methanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (7-bromo-2,3-dihydro-1,4-benzodioxin-6-yl)(thiophen-2-yl)methanone
• 英文别名: (6-bromo-2,3-dihydro-1,4-benzodioxin-7-yl)-thiophen-2-ylmethanone
• 化学式: C₁₃H₉BrO₃S
• mdl: MFCD09063358
• 分子量: 325.183
• InChiKey: LUQYSWDRKJOMJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (7-bromo-2,3-dihydro-1,4-benzodioxin-6-yl)(thiophen-2-yl)methanone 在 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 8-hydroxy-8-(thiophen-2-yl)-2,3,7,8-tetrahydro-6H-[1,4]dioxino[2,3-f]isoindol-6-one
  参考文献：
  名称：

  o-Acylbenzonitriles: Synthesis and Heterocyclization under Acid Hydrolysis of the Cyano Group

  摘要：

  2-Cyanobenzophenones were synthesized by reaction of 2-bromobenzophenones with copper(I) cyanide in DMF, and their transformations involving acid hydrolysis of the cyano group were studied. Reactions of o-benzoylbenzonitriles with trifluoroacetic acid in the presence or in the absence of sulfuric acid afforded 3-hydroxyphthalimidines in high yields. Under analogous conditions, benzonitriles having no acyl group in the ortho position were converted to the corresponding benzamides. 2-Cyanobenzophenones reacted with sulfuric acid in the absence of trifluoroacetic acid to give only substituted anthraquinones.

  DOI：

  10.1134/s1070428018030065
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 6-溴-1,4-苯并恶烷 在 aluminum (III) chloride 作用下， 以 四氯化碳 为溶剂， 以76%的产率得到(7-bromo-2,3-dihydro-1,4-benzodioxin-6-yl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  o-Acylbenzonitriles: Synthesis and Heterocyclization under Acid Hydrolysis of the Cyano Group

  摘要：

  2-Cyanobenzophenones were synthesized by reaction of 2-bromobenzophenones with copper(I) cyanide in DMF, and their transformations involving acid hydrolysis of the cyano group were studied. Reactions of o-benzoylbenzonitriles with trifluoroacetic acid in the presence or in the absence of sulfuric acid afforded 3-hydroxyphthalimidines in high yields. Under analogous conditions, benzonitriles having no acyl group in the ortho position were converted to the corresponding benzamides. 2-Cyanobenzophenones reacted with sulfuric acid in the absence of trifluoroacetic acid to give only substituted anthraquinones.

  DOI：

  10.1134/s1070428018030065

文献信息

• Direct synthesis of ethers from aldehydes and ketones. One-pot reductive etherification of benzaldehydes, alkyl aryl ketones, and benzophenones
  作者：S. S. Mochalov、A. N. Fedotov、E. V. Trofimova、N. S. Zefirov

  DOI：10.1134/s1070428016040047

  日期：2016.4

  Benzyl alcohols formed by the reduction of benzaldehydes, alkyl aryl ketones, and benzophenones with sodium tetrahydridoborate in alcohols undergo in situ etherification with the solvent in the presence of a catalytic amount of HCl. Thus the process may be regarded as one-pot transformation of carbonyl compounds into the corresponding benzyl ethers. The yields of ethers depend on the substituent nature

  通过在醇中催化量的四氢硼酸钠将苯甲醛，烷基芳基酮和二苯甲酮还原而形成的苄醇在催化量的HCl的存在下与溶剂进行原位醚化。因此，该方法可以被认为是羰基化合物一锅转化为相应的苄基醚。醚的产率取决于初始羰基化合物的芳族片段中的取代基性质以及用作还原介质的醇。
• o-Acylbenzonitriles: Synthesis and Heterocyclization under Acid Hydrolysis of the Cyano Group
  作者：S. S. Mochalov、A. N. Fedotov、E. V. Trofimova、N. S. Zefirov

  DOI：10.1134/s1070428018030065

  日期：2018.3

  2-Cyanobenzophenones were synthesized by reaction of 2-bromobenzophenones with copper(I) cyanide in DMF, and their transformations involving acid hydrolysis of the cyano group were studied. Reactions of o-benzoylbenzonitriles with trifluoroacetic acid in the presence or in the absence of sulfuric acid afforded 3-hydroxyphthalimidines in high yields. Under analogous conditions, benzonitriles having no acyl group in the ortho position were converted to the corresponding benzamides. 2-Cyanobenzophenones reacted with sulfuric acid in the absence of trifluoroacetic acid to give only substituted anthraquinones.