3-<<(4-fluorophenyl)telluro>methyl>chromanone | 143565-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-<<(4-fluorophenyl)telluro>methyl>chromanone
• 英文别名: 3-{[(4-Fluorophenyl)tellanyl]methyl}-2,3-dihydro-4H-1-benzopyran-4-one；3-[(4-fluorophenyl)tellanylmethyl]-2,3-dihydrochromen-4-one
• CAS: 143565-08-6
• 化学式: C₁₆H₁₃FO₂Te
• 分子量: 383.876
• InChiKey: XUCYUXRIXJIVIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<<(4-fluorophenyl)telluro>methyl>chromanone 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 生成 3-methylenechroman-4-one
  参考文献：
  名称：

  The chemistry of acyl tellurides: generation and trapping of acyl radicals, including aryltellurium group transfer

  摘要：

  DOI：

  10.1021/ja00047a066
• 作为产物：
  描述：

  bis(4-fluorophenyl)ditelluride 在 sodium tetrahydroborate 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 3-<<(4-fluorophenyl)telluro>methyl>chromanone
  参考文献：
  名称：

  Photoinduced Free Radical Chemistry of the Acyl Tellurides: Generation, Inter- and Intramolecular Trapping, and ESR Spectroscopic Identification of Acyl Radicals

  摘要：

  Acyl tellurides are prepared in good to excellent yield by the reaction of sodium aryl tellurides with acyl chlorides, or mixed anhydrides, and are found to be moderately air-stable substances. In contrast to previous literature reports, acyl tellurides of aryl and vinyl carboxylic acids are found to be excellent sources of acyl radicals on photolysis with a simple white light source. The acyl radicals so generated may be trapped intermolecularly by dichalcogenides, or by TEMPO in excellent yield. Trapping by N-tert-butyl-alpha-phenyl nitrone produces a stable nitroxide radical which has been characterized by ESR spectroscopy. The very efficient trapping of acyl radicals by acyl tellurides themselves is demonstrated by a crossover experiment. Acyl tellurides are shown to participate in very efficient radical cyclization reactions onto alkenes with the formation of five-, six-, and eight-membered rings. The immediate products of the cyclizations onto alkenes are alpha-[(aryltelluro)methyl] ketones and the chemistry of these relatively unstable species is briefly described. Treatment with hydrogen peroxide affords alpha-methylene ketones in high yield. When elimination of the aryl telluro group is not possible the alpha-[(aryltelluro)methyl] ketones are stable species that may subsequently be employed in further radical chain reactions, for example with tributyltin hydride and methyl acrylate. Cyclization onto alkynes yields alpha-[(aryltelluro)methylene] ketones which are stable species and which take part in substitution reactions with higher order cuprates or with diphenyl diselenide.

  DOI：

  10.1021/ja00099a011

文献信息

• Photoinduced Free Radical Chemistry of the Acyl Tellurides: Generation, Inter- and Intramolecular Trapping, and ESR Spectroscopic Identification of Acyl Radicals
  作者：David Crich、Chen Chen、Jae-Taeg Hwang、Hongwei Yuan、Aristotle Papadatos、Robert I. Walter

  DOI：10.1021/ja00099a011

  日期：1994.10

  Acyl tellurides are prepared in good to excellent yield by the reaction of sodium aryl tellurides with acyl chlorides, or mixed anhydrides, and are found to be moderately air-stable substances. In contrast to previous literature reports, acyl tellurides of aryl and vinyl carboxylic acids are found to be excellent sources of acyl radicals on photolysis with a simple white light source. The acyl radicals so generated may be trapped intermolecularly by dichalcogenides, or by TEMPO in excellent yield. Trapping by N-tert-butyl-alpha-phenyl nitrone produces a stable nitroxide radical which has been characterized by ESR spectroscopy. The very efficient trapping of acyl radicals by acyl tellurides themselves is demonstrated by a crossover experiment. Acyl tellurides are shown to participate in very efficient radical cyclization reactions onto alkenes with the formation of five-, six-, and eight-membered rings. The immediate products of the cyclizations onto alkenes are alpha-[(aryltelluro)methyl] ketones and the chemistry of these relatively unstable species is briefly described. Treatment with hydrogen peroxide affords alpha-methylene ketones in high yield. When elimination of the aryl telluro group is not possible the alpha-[(aryltelluro)methyl] ketones are stable species that may subsequently be employed in further radical chain reactions, for example with tributyltin hydride and methyl acrylate. Cyclization onto alkynes yields alpha-[(aryltelluro)methylene] ketones which are stable species and which take part in substitution reactions with higher order cuprates or with diphenyl diselenide.
• The chemistry of acyl tellurides: generation and trapping of acyl radicals, including aryltellurium group transfer
  作者：Chen Chen、David Crich、Aristotle Papadatos

  DOI：10.1021/ja00047a066

  日期：1992.10