3-(5-bromo-2-thienyl)phthalide | 186000-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-(5-bromo-2-thienyl)phthalide
• 英文别名: 3-(4-bromo-2-thienyl)-1(3H)-isobenzofuranone；3-(5-bromothiophen-2-yl)-3H-2-benzofuran-1-one
• CAS: 186000-49-7
• 化学式: C₁₂H₇BrO₂S
• 分子量: 295.156
• InChiKey: YIVFTJHTQZWUAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(5-bromo-2-thienyl)phthalide 在 劳森试剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 1-(5-bromo-2-thienyl)-3-(2-thienyl)benzo[c]thiophene
  参考文献：
  名称：

  Studies in the Dithienylbenzo[c]thiophene Series

  摘要：

  A number of derivatives of 1,3-dithienylbenzo[c]thiophene have been synthesized. The mono-and dicarboxaldehydes have been elaborated to give new vinylenes and cyanovinylenes. beta-Dodecyl- and hexyl-substituted analogues have been prepared. Results from cyclic voltammetric investigation as well as fluorescence studies are reported.

  DOI：

  10.1021/jo980246a
• 作为产物：
  描述：

  2-(5-bromo-2-thenoyl)benzoic acid 在 盐酸 、 sodium tetrahydroborate 、 碳酸氢钠 作用下， 反应 2.0h， 生成 3-(5-bromo-2-thienyl)phthalide
  参考文献：
  名称：

  Studies in the Dithienylbenzo[c]thiophene Series

  摘要：

  A number of derivatives of 1,3-dithienylbenzo[c]thiophene have been synthesized. The mono-and dicarboxaldehydes have been elaborated to give new vinylenes and cyanovinylenes. beta-Dodecyl- and hexyl-substituted analogues have been prepared. Results from cyclic voltammetric investigation as well as fluorescence studies are reported.

  DOI：

  10.1021/jo980246a

文献信息

• Cr³⁺-Mediated Addition of Arylzincs to Aldehydes
  作者：Yoshihiro Ogawa、Mitsuo Mori、Akihiro Saiga、Kentaro Takagi

  DOI：10.1246/cl.1996.1069

  日期：1996.12

  Addition of arylzincs to aldehydes was achieved by making use of the novel transmetallation of arylzincs into Cr3+ compounds. Various α-substituted benzyl alcohols or 3-substituted 1(3H)-isobenzofuranones, containing reactive functional groups, were synthesized in good yields. Me3SiCl exerted beneficial effects on the reaction.

  通过将芳基锌转化为 Cr3+ 化合物的新型转金属化反应，实现了芳基锌对醛的加成。采用多种包含反应性官能团的 α-取代苄醇或 3-取代 1(3H)-异苯并呋喃酮，在良好的产率下被合成。Me3SiCl 对反应产生了有益的影响。
• Nucleophilic Additions of Arylzinc Compounds to Aldehydes Mediated by CrCl₃:  Efficient and Facile Synthesis of Functionalized Benzhydrols, 1(3<i>H</i>)-Isobenzofuranones, Benzyl Alcohols, or Diaryl Ketones
  作者：Yoshihiro Ogawa、Akihiro Saiga、Mitsuo Mori、Takanori Shibata、Kentaro Takagi

  DOI：10.1021/jo991444k

  日期：2000.2.1

  benzhydrols 4a-f in good yields. From arylzinc compounds 1a,b, 3-aryl-1(3H)-isobenzofuranones 3a-f were given by the CrCl(3)-mediated reaction with arylaldehydes 2a-f. Diaryl ketones 5a-e were obtained in good yields by the addition of excess amount of benzaldehyde as an oxidant to the resulting solution after the CrCl(3)-mediated reaction between arylzinc compounds 1c-g and arylaldehydes 2b,g was completed

  在化学计量的CrCl（3）和三甲基氯硅烷（TMSCl）的存在下，芳基锌化合物1c-h向芳基醛2a，b，g的亲核加成反应在室温下平稳进行，以良好的收率得到相应的苯甲醇4a-f。从芳基锌化合物1a，b通过CrCl（3）介导的与芳基醛2a-f的反应得到3-芳基-1（3H）-异苯并呋喃酮3a-f。在芳基锌化合物1c-g与芳基醛2b，g之间完成CrCl（3）介导的反应后，通过向所得溶液中添加过量的苯甲醛作为氧化剂，以高收率获得二芳基酮5a-e。在芳基锌化合物1a，d，f与烷基6b-f的亲核加成中，在添加醛之前，需要用CrCl（3）处理芳基锌化合物，以防止可烯化的醛对芳基锌化合物的快速原型脱锌。在这些CrCl（3）介导的芳基锌化合物与醛的亲核加成反应中，芳基铬（III）可能是反应性中间体。
• Studies in the Dithienylbenzo[<i>c</i>]thiophene Series
  作者：A. K. Mohanakrishnan、M. V. Lakshmikantham、Carol McDougal、Michael P. Cava、Jeffrey W. Baldwin、Robert M. Metzger

  DOI：10.1021/jo980246a

  日期：1998.5.1

  A number of derivatives of 1,3-dithienylbenzo[c]thiophene have been synthesized. The mono-and dicarboxaldehydes have been elaborated to give new vinylenes and cyanovinylenes. beta-Dodecyl- and hexyl-substituted analogues have been prepared. Results from cyclic voltammetric investigation as well as fluorescence studies are reported.