3-(4-碘苯基)-3H-2-苯并呋喃-1-酮 | 241491-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 3-(4-碘苯基)-3H-2-苯并呋喃-1-酮
• 英文名称: 3-(4'-Iodophenyl)phthalide
• 英文别名: 3-(4-Iodophenyl)isobenzofuran-1(3H)-one；3-(4-iodophenyl)-3H-2-benzofuran-1-one
• CAS: 241491-71-4
• 化学式: C₁₄H₉IO₂
• 分子量: 336.129
• InChiKey: XNWFZRKLJMZTKY-UHFFFAOYSA-N

物化性质

• 熔点：
  102-105 °C
• 沸点：
  426.8±45.0 °C(Predicted)
• 密度：
  1.747±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-碘苯甲酰基)苯甲酸 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 氢气 、 cesium fluoride 作用下， 以 甲醇 、 四氯化碳 、 乙腈 为溶剂， 70.0 ℃ 、2.03 MPa 条件下， 反应 28.0h， 生成 3-(4-碘苯基)-3H-2-苯并呋喃-1-酮
  参考文献：
  名称：

  An Alternative Method for the Synthesis of γ-Lactones by Using Cesium Fluoride-Celite/Acetonitrile Combination

  摘要：

  A variety of 2-(1-bromoalkyl) benzoic acids 4 undergo intramolecular nucleophilic substitution reaction when treated with a CsF-Celite as solid base in acetonitrile under reflux condition to give the corresponding cyclized phthalides in moderate to very good yield. These 2-(1-bromoalkyl) benzoic acids 4 are formed by the alpha-bromination of 2-alkylbenzoic acids 3 using N-bromosuccinimide and a catalytic amount of alpha,alpha'-azoisobutyronitrile in carbon tetrachloride under reflux.

  DOI：

  10.1081/scc-120024003

文献信息

• Reactivity in the formation of lactones from aromatic carboxylic acids with organohypervalent iodine compounds in the Suárez system
  作者：Takahito Muraki、Hideo Togo、Masataka Yokoyama

  DOI：10.1039/a900791a

  日期：——

  The reactivity of various iodanes, such as (diacetoxyiodo)arenes, the Dess–Martin reagent, and (arylsulfonyloxy)benziodoxolones, with (o-alkyl)- and (o-phenyl)arenecarboxylic acids in the presence of iodine (Suárez system) was studied to give the corresponding lactones via oxygen-centered radicals. (Diacetoxyiodo)arenes gave the lactones in good yields, while 1-(arylsulfonyloxy)benziodoxolones gave lactones together with the iodinated lactones. The Dess–Martin reagent also showed the same reactivity as (diacetoxyiodo)arenes to give the lactones. Among them, (diacetoxyiodo)toluene showed the best reactivity for the conversion of these carboxylic acids to the corresponding lactones.

  研究了各种碘试剂，如(二乙酰氧基碘)芳烃、Dess-Martin试剂和(芳磺酰氧基)苯碘氧杂环酮，与(邻烷基)和(邻苯基)芳香羧酸在碘存在下(Suárez系统)的反应活性，经由氧中心自由基生成相应的内酯。(二乙酰氧基碘)芳烃可以高产率地生成内酯，而1-(芳磺酰氧基)苯碘氧杂环酮则同时生成碘代内酯。Dess-Martin试剂与(二乙酰氧基碘)芳烃显示出相同的反应活性，也能生成内酯。其中，(二乙酰氧基碘)甲苯对于这些羧酸转化为相应内酯的反应活性最佳。
• An Alternative Method for the Synthesis of γ-Lactones by Using Cesium Fluoride-Celite/Acetonitrile Combination
  作者：Khan, Khalid Mohammed、Hayat, Safdar、Zia-Ullah、Atta-ur-Rahman、Iqbal-Choudhary、Maharvi, Ghulam Murtaza、Bayert, Ernst

  DOI：10.1081/scc-120024003

  日期：2003.9

  A variety of 2-(1-bromoalkyl) benzoic acids 4 undergo intramolecular nucleophilic substitution reaction when treated with a CsF-Celite as solid base in acetonitrile under reflux condition to give the corresponding cyclized phthalides in moderate to very good yield. These 2-(1-bromoalkyl) benzoic acids 4 are formed by the alpha-bromination of 2-alkylbenzoic acids 3 using N-bromosuccinimide and a catalytic amount of alpha,alpha'-azoisobutyronitrile in carbon tetrachloride under reflux.
• Bayer, Ernst; Hayat, Safdar; Atta-Ur-Rahman, Arzneimittel-Forschung/Drug Research, 2005, vol. 55, # 10, p. 588 - 597
  作者：Bayer, Ernst、Hayat, Safdar、Atta-Ur-Rahman、Choudhary, M. Iqbal、Khan, Khalid Mohammed、Shah, Syed Tasadaque Ali、Imran-Ul-Haq、Anwar, M. Usman、Voelter, Wolfgang

  DOI：——

  日期：——

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