Se-phenyl 2-(allyloxy)selenobenzoate | 122080-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Se-phenyl 2-(allyloxy)selenobenzoate
• 英文别名: Se-Phenyl O-Allylselenosalicylate；Se-phenyl 2-prop-2-enoxybenzenecarboselenoate
• CAS: 122080-54-0
• 化学式: C₁₆H₁₄O₂Se
• 分子量: 317.246
• InChiKey: LPJYOYBTXPODHY-UHFFFAOYSA-N

物化性质

• 沸点：
  442.7±47.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Se-phenyl 2-(allyloxy)selenobenzoate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.5h， 以52%的产率得到3-甲基-2,3-二氢-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  合成中的酰基自由基环化。第2部分进一步的取代基对6-庚烯酰基自由基的环化方式和效率的影响。

  摘要：

  在试图确定的因素影响- / -中的制备，并用三丁基锡氢化物反应的各种杂原子取代的硒醇酯6- heptenoyl自由基环化的选择性。引入7-苯硫基部分导致在-模式下清洁，高产率的环化。有人为6-庚烯基自由基环化的可逆性提供了证据。

  DOI：

  10.1016/s0040-4020(01)89779-9
• 作为产物：
  描述：

  2-allyloxybenzoyl chloride 在 sodium tetrahydroborate 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 Se-phenyl 2-(allyloxy)selenobenzoate
  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

• 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
• Bachi, Mario D.; Denenmark, Daniella, Heterocycles, 1989, vol. 28, # 2, p. 583 - 588
  作者：Bachi, Mario D.、Denenmark, Daniella

  DOI：——

  日期：——
• Inhibition of Rearrangements in Stannane-Mediated Radical Reduction Reactions by Catalytic Quantities of Diphenyl Diselenide. An Example of Polarity Reversal Catalysis
  作者：David Crich、Qingwei Yao

  DOI：10.1021/jo00106a018

  日期：1995.1

  The presence of only 10 mol % of PhSeH, PhSeSePh (reduced in situ to PhSeH), and, to a lesser extent, PhSH has a dramatic effect on the efficiency of stannane-mediated free radical rearrangement reactions owing to the superior hydrogen donating qualities of PhSeH and PhSH. Slow radical rearrangements can be prevented altogether, and the yields of even moderately rapid rearrangements significantly diminished. The addition of 10 mol % of PhSeSePh to stannane-mediated aryl radical cyclizations is advantageous as the initial, rapid, 5-hexenyl rearrangement is not impaired but the subsequent, slower neophyl rearrangement is effectively minimized, resulting in the formation of vastly improved 5-exo/6-endo ratios.
• Carbonyl Radical Cyclizations: Preparation of Some Heterocyclic Ketones
  作者：David Crich、K. Angeline Eustace、Timothy J. Ritchie

  DOI：10.3987/com-88-s27

  日期：——
• CRICH, DAVID;EUSTACE, K. ANGELINE;FORTT, SIMON M.;RITCHIE, TIMOTHY J., TETRAHEDRON, 46,(1990) N, C. 2135-2148
  作者：CRICH, DAVID、EUSTACE, K. ANGELINE、FORTT, SIMON M.、RITCHIE, TIMOTHY J.

  DOI：——

  日期：——