N-acetyl-5-acetylamino-1-methoxytryptamine | 1006607-57-3

• 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: N-acetyl-5-acetylamino-1-methoxytryptamine
• 英文别名: N(b)-acetyl-5-acetylamino-1-methoxytryptamine；N-[2-(5-acetamido-1-methoxyindol-3-yl)ethyl]acetamide
• CAS: 1006607-57-3
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: ZXMYHZSJAWVMCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-acetyl-1-methoxy-5-nitrotryptamine 、 乙酸酐 在 tin 、 溶剂黄146 作用下， 生成 N-acetyl-5-acetylamino-1-methoxytryptamine
  参考文献：
  名称：

  Substituent Effects on Ultraviolet Absorption Spectra of 5-Substituted Nb-Acetyl-1-methoxytryptamines Studied by Density Functional Theory Calculations

  摘要：

  Density functional theory (DFT) calculations were performed for twelve 5-substituted N-b-acetyl-1-methoxytryptamines (5-X: NO2, SO2CH3, CN, CF3, Cl, H, CH3, OH, OCH3, NHCOCH3, NH2, N(CH3)(2)) in methanol. The respective HOMO -> LUMO and HOMO-1 -> LUMO singly excited configurations are mainly responsible for the lowest and the second singlet excited states (S-1 and S-2)Observed UV absorption spectra of 5-H, 5-NHAc, and 5-CH3 derivatives are well predicted by simple time-dependent DFT calculations. Distinct substituent effects are found with respect to the energies of MOs responsible for S-1 <- S-0 and S-2 <- S-0 transitions. Both HOMO-1 and HOMO are destabilized by electron-donating groups, and stabilized by electron-withdrawing groups. LUMO+1 of 5-NO2 derivative should be classified into normal LUMO, which are found for eleven other derivatives as well as indole. Normal LUMO is not significantly affected in energy by electron-donating groups, but stabilized by electron-withdrawing groups.

  DOI：

  10.3987/com-07-s(u)2

文献信息

• Substituent Effects on Ultraviolet Absorption Spectra of 5-Substituted Nb-Acetyl-1-methoxytryptamines Studied by Density Functional Theory Calculations
  作者：Kunihiro Tokumura、Kenta Imai、Akio Hayashi、Tomonori Ida、Masanori Somei

  DOI：10.3987/com-07-s(u)2

  日期：——

  Density functional theory (DFT) calculations were performed for twelve 5-substituted N-b-acetyl-1-methoxytryptamines (5-X: NO2, SO2CH3, CN, CF3, Cl, H, CH3, OH, OCH3, NHCOCH3, NH2, N(CH3)(2)) in methanol. The respective HOMO -> LUMO and HOMO-1 -> LUMO singly excited configurations are mainly responsible for the lowest and the second singlet excited states (S-1 and S-2)Observed UV absorption spectra of 5-H, 5-NHAc, and 5-CH3 derivatives are well predicted by simple time-dependent DFT calculations. Distinct substituent effects are found with respect to the energies of MOs responsible for S-1 <- S-0 and S-2 <- S-0 transitions. Both HOMO-1 and HOMO are destabilized by electron-donating groups, and stabilized by electron-withdrawing groups. LUMO+1 of 5-NO2 derivative should be classified into normal LUMO, which are found for eleven other derivatives as well as indole. Normal LUMO is not significantly affected in energy by electron-donating groups, but stabilized by electron-withdrawing groups.