4-Carbomethoxy-2,3-dihydro-3,3-dimethyl-7-methoxybenzofuran

• 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: 4-Carbomethoxy-2,3-dihydro-3,3-dimethyl-7-methoxybenzofuran
• 英文别名: methyl 7-methoxy-3,3-dimethyl-2H-1-benzofuran-4-carboxylate
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: CVZFNSRPJOVFDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-羟基-2-碘-4-甲氧基苯甲醛 在 potassium cyanide 、 manganese(IV) oxide 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 23.0h， 生成 4-Carbomethoxy-2,3-dihydro-3,3-dimethyl-7-methoxybenzofuran
  参考文献：
  名称：

  Inhibition of Rearrangements in Stannane-Mediated Radical Reduction Reactions by Catalytic Quantities of Diphenyl Diselenide. An Example of Polarity Reversal Catalysis

  摘要：

  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.

  DOI：

  10.1021/jo00106a018

文献信息

• Design, synthesis, application and recovery of a minimally fluorous diaryl diselenide for the catalysis of stannane-mediated radical chain reactions
  作者：David Crich、Xiaolin Hao、Mathew Lucas

  DOI：10.1016/s0040-4020(99)00902-3

  日期：1999.12

  diselenide is described. On reduction in situ with tributylstannane this diselenide provides a fluorous selenol which is effective in inhibiting a range of stannane-mediated radical rearrangements, including a cyclopropylcarbinyl ring opening. A method for the recovery of the fluorous diselenide involving continuous extraction in a modified, cooled continuous extractor is described.

  描述了最低氟（52％F）二芳基二硒化物的合成。在用三丁基锡烷原位还原时，该二硒化物提供了一种氟硒醇，其有效抑制了由锡烷介导的自由基重排的范围，包括环丙基羰基的开环。描述了一种回收二硒氟的方法，该方法包括在改良的冷却的连续萃取器中连续萃取。