ethyl 4-cyano-3-(1,1-dimethylethyl)benzoate

• 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: ethyl 4-cyano-3-(1,1-dimethylethyl)benzoate
• 英文别名: Ethyl 3-tert-butyl-4-cyanobenzoate
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: LRWMQWUDGUQGBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氰基苯甲酸乙酯 、 溴代叔丁烷 在 三乙烯二胺 、 六正丁基二锡 作用下， 以 苯 为溶剂， 反应 100.0h， 以70%的产率得到ethyl 4-cyano-3-(1,1-dimethylethyl)benzoate
  参考文献：
  名称：

  Homolytic Base-Promoted Aromatic Alkylations by Alkyl Halides¹

  摘要：

  Electron-transfer chain reactions leading to regioselective alkylations of benzenes bearing electron-withdrawing substituents can be observed with alkyl halides in the presence of the radical initiator (Bu3Sn)(2) and the proton acceptor 1,4-diazabicyclo[2.2.2]octane (DABCO). Yields vary from low to high depending on the benzene derivatives. The role of DABCO is to abstract a proton from the substituted cyclohexadienyl adduct radical to form a radical anion which then transfers an electron to RX and is converted to the alkylated product itself. The rate of this electron-transfer step is probably not fast enough to sustain a good radical chain reaction so that further generation of R-. from excess (Bu3Sn)(2) and RX is necessary.

  DOI：

  10.1021/jo9818982

文献信息

• Homolytic Base-Promoted Aromatic Alkylations by Alkylmercury Halides¹
  作者：Glen A. Russell、Ping Chen、Byeong Hyo Kim、Ragine Rajaratnam

  DOI：10.1021/ja971809n

  日期：1997.9.1

  Electron transfer chain reactions leading to substitution in electronegatively substituted benzene derivatives can be observed with alkylmercury halides in the presence of proton acceptors such as ...

  在质子受体的存在下，可以用烷基汞卤化物观察到导致电负性取代的苯衍生物取代的电子转移链反应，例如……
• Homolytic Base-Promoted Aromatic Alkylations by Alkyl Halides¹
  作者：Chen Wang、Glen A. Russell、Walter S. Trahanovsky

  DOI：10.1021/jo9818982

  日期：1998.12.1

  Electron-transfer chain reactions leading to regioselective alkylations of benzenes bearing electron-withdrawing substituents can be observed with alkyl halides in the presence of the radical initiator (Bu3Sn)(2) and the proton acceptor 1,4-diazabicyclo[2.2.2]octane (DABCO). Yields vary from low to high depending on the benzene derivatives. The role of DABCO is to abstract a proton from the substituted cyclohexadienyl adduct radical to form a radical anion which then transfers an electron to RX and is converted to the alkylated product itself. The rate of this electron-transfer step is probably not fast enough to sustain a good radical chain reaction so that further generation of R-. from excess (Bu3Sn)(2) and RX is necessary.