methyl [2-(cyclopent-2-en-1-yl)anilino]acetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl [2-(cyclopent-2-en-1-yl)anilino]acetate
• 英文别名: Methyl [2-(cyclopent-2-en-1-yl)anilino]-acetate；methyl 2-(2-cyclopent-2-en-1-ylanilino)acetate
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: JYADOYKIMXJJDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• 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：

  methyl [2-(cyclopent-2-en-1-yl)anilino]acetate 在 lithium hydroxide monohydrate 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-[N-acetyl-2-(cyclopent-2-en-1-yl)anilino]acetic acid
  参考文献：
  名称：

  Synthesis of Epimethanetriyloxazoloand Epimethanetriylimidazobenzazocinones and -benzazoninones from syn- and anti-Atropisomers of N-Acyl-N-[2-(cycloalk-2-en-1-yl)-6-methylphenyl]glycines

  摘要：

  The major product of intramolecular [3 + 2]-cycloaddition of munchnones generated by heating syn- and anti-atropisomers of N-acetyl-N-[2-(cyclopent-2-en-1-yl)-6-methyl-, 2,4-dimethyl-, 2,5-dimethylphenyl)- and N-acetyl-N-[2-(cyclohex-2-en-1-yl)-6-methylphenyl]glycines with acetic anhydride was that formed from the anti isomer. Isomeric glycine derivatives having no methyl group in the ortho position of the aromatic ring gave rise to (1S*,3aR*,4S*,7S*,13S*)-1-methyl- and (1S*,3aR*,4S*,7S*,13S*)-3a-acetyl-1-methyl-4,5,6,7- tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin-3(3aH)-one as the major product. Treatment of 1,11-dimethyl- and 1,9,11-trimethyl-4,5,6,7-tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin- 3(3aH)-ones with methylamine in methanol on heating in a sealed ampule afforded epimethanetriylimidazobenzazocinones, whereas acid-stable compound with a methanocyclopenta[c]quinoline skeleton was formed under similar conditions from the 1,8,11-trimethyl analog.

  DOI：

  10.1134/s1070428018100147
• 作为产物：
  描述：

  2-环戊-2-烯-1-基苯胺 、 溴乙酸甲酯 在 potassium carbonate 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以48%的产率得到methyl [2-(cyclopent-2-en-1-yl)anilino]acetate
  参考文献：
  名称：

  Synthesis of Epimethanetriyloxazoloand Epimethanetriylimidazobenzazocinones and -benzazoninones from syn- and anti-Atropisomers of N-Acyl-N-[2-(cycloalk-2-en-1-yl)-6-methylphenyl]glycines

  摘要：

  The major product of intramolecular [3 + 2]-cycloaddition of munchnones generated by heating syn- and anti-atropisomers of N-acetyl-N-[2-(cyclopent-2-en-1-yl)-6-methyl-, 2,4-dimethyl-, 2,5-dimethylphenyl)- and N-acetyl-N-[2-(cyclohex-2-en-1-yl)-6-methylphenyl]glycines with acetic anhydride was that formed from the anti isomer. Isomeric glycine derivatives having no methyl group in the ortho position of the aromatic ring gave rise to (1S*,3aR*,4S*,7S*,13S*)-1-methyl- and (1S*,3aR*,4S*,7S*,13S*)-3a-acetyl-1-methyl-4,5,6,7- tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin-3(3aH)-one as the major product. Treatment of 1,11-dimethyl- and 1,9,11-trimethyl-4,5,6,7-tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin- 3(3aH)-ones with methylamine in methanol on heating in a sealed ampule afforded epimethanetriylimidazobenzazocinones, whereas acid-stable compound with a methanocyclopenta[c]quinoline skeleton was formed under similar conditions from the 1,8,11-trimethyl analog.

  DOI：

  10.1134/s1070428018100147

文献信息

• Synthesis of Epimethanetriyloxazoloand Epimethanetriylimidazobenzazocinones and -benzazoninones from syn- and anti-Atropisomers of N-Acyl-N-[2-(cycloalk-2-en-1-yl)-6-methylphenyl]glycines
  作者：L. A. Aleksandrova、A. A. Fatykhov、A. R. Gataullina、E. A. Kantor、R. R. Gataullin

  DOI：10.1134/s1070428018100147

  日期：2018.10

  The major product of intramolecular [3 + 2]-cycloaddition of munchnones generated by heating syn- and anti-atropisomers of N-acetyl-N-[2-(cyclopent-2-en-1-yl)-6-methyl-, 2,4-dimethyl-, 2,5-dimethylphenyl)- and N-acetyl-N-[2-(cyclohex-2-en-1-yl)-6-methylphenyl]glycines with acetic anhydride was that formed from the anti isomer. Isomeric glycine derivatives having no methyl group in the ortho position of the aromatic ring gave rise to (1S*,3aR*,4S*,7S*,13S*)-1-methyl- and (1S*,3aR*,4S*,7S*,13S*)-3a-acetyl-1-methyl-4,5,6,7- tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin-3(3aH)-one as the major product. Treatment of 1,11-dimethyl- and 1,9,11-trimethyl-4,5,6,7-tetrahydro-1,4,7-epimethanetriyl[1,3]oxazolo[3,4-a][1]benzazocin- 3(3aH)-ones with methylamine in methanol on heating in a sealed ampule afforded epimethanetriylimidazobenzazocinones, whereas acid-stable compound with a methanocyclopenta[c]quinoline skeleton was formed under similar conditions from the 1,8,11-trimethyl analog.