ethyl 4-[(1,1-dimethylallyl)amino]benzoate | 288098-52-2

• 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-[(1,1-dimethylallyl)amino]benzoate
• 英文别名: ethyl 4-(2-methylbut-3-en-2-ylamino)benzoate
• CAS: 288098-52-2
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: KFYKDCQBIRZKRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-[(1,1-dimethylallyl)amino]benzoate 在 mercury(II) diacetate 、 对甲苯磺酸 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 反应 16.17h， 生成 ethyl 2,2-dimethyl-3,4-dihydro-1H-quinoline-6-carboxylate
  参考文献：
  名称：

  摘要：

  Cyclization of the carbamate of 2-(dimethylallyl)aniline with phenylselanyl chloride (benzeneselenenyl chloride) gave a 1:1 mixture of a dihydroindole and a tetrahydroquinoline. With phenylselanyl bromide only the dihydroindole was obtained. Addition of methanol to the silica used in the procedure trapped the reaction at the non-cyclized stage forming a 3-methoxy-3-methyl-2-(phenylselanyl)butyl side chain. The sulfonamide of 2-(dimethylallyl)aniline only formed the dihydroindole with phenylselanyl chloride. The corresponding trifluoroacetamide derivative did not form any cyclized product under the same conditions. The dihydroindole could be converted into the corresponding alkene by oxidative removal of the phenylseleno group. 4-Ethoxycarbonyl-2-(3,3-dimethylallyl)aniline cyclized with mercuric nitrate to give, after a reductive workup, a 2,2-dimethyltetrahydroquinoline. The X-ray crystal structures of ethyl N-{2-[3-methoxy-3-methyl-2-(phenylselanyl)butyl] phenyl} carbamate and 2-[1-methyl-1-(phenylselanyl)ethyl]-1-[(4-methylphenyl)sulfonyl]indoline are reported.

  DOI：

  10.1071/ch99109
• 作为产物：
  描述：

  Ethyl 4-(2-methylbut-3-yn-2-ylamino)benzoate 在 Lindlar's catalyst 氢气 作用下， 以 乙醚 为溶剂， 以91%的产率得到ethyl 4-[(1,1-dimethylallyl)amino]benzoate
  参考文献：
  名称：

  Cooper; Lucas; Taylor, Synthesis, 2001, # 4, p. 621 - 625

  摘要：

  DOI：

文献信息

• Cooper; Lucas; Taylor, Synthesis, 2001, # 4, p. 621 - 625
  作者：Cooper、Lucas、Taylor、Ward、Williamson

  DOI：——

  日期：——
• ——
  作者：Matthew A. Cooper、Craig L. Francis、Jeffrey W. Holman、Bruno Kasum、Thomas Taverner、Edward R. T. Tiekink、A. David Ward

  DOI：10.1071/ch99109

  日期：——

  Cyclization of the carbamate of 2-(dimethylallyl)aniline with phenylselanyl chloride (benzeneselenenyl chloride) gave a 1:1 mixture of a dihydroindole and a tetrahydroquinoline. With phenylselanyl bromide only the dihydroindole was obtained. Addition of methanol to the silica used in the procedure trapped the reaction at the non-cyclized stage forming a 3-methoxy-3-methyl-2-(phenylselanyl)butyl side chain. The sulfonamide of 2-(dimethylallyl)aniline only formed the dihydroindole with phenylselanyl chloride. The corresponding trifluoroacetamide derivative did not form any cyclized product under the same conditions. The dihydroindole could be converted into the corresponding alkene by oxidative removal of the phenylseleno group. 4-Ethoxycarbonyl-2-(3,3-dimethylallyl)aniline cyclized with mercuric nitrate to give, after a reductive workup, a 2,2-dimethyltetrahydroquinoline. The X-ray crystal structures of ethyl N-2-[3-methoxy-3-methyl-2-(phenylselanyl)butyl] phenyl} carbamate and 2-[1-methyl-1-(phenylselanyl)ethyl]-1-[(4-methylphenyl)sulfonyl]indoline are reported.