1-(4'-nitrophenyl)indole-2-carboxaldehyde | 343238-34-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4'-nitrophenyl)indole-2-carboxaldehyde
• 英文别名: N-(4'-nitrophenyl)indole-2-carboxaldehyde；1-(4-Nitrophenyl)indole-2-carbaldehyde；1-(4-nitrophenyl)indole-2-carbaldehyde
• CAS: 343238-34-6
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: GEEUDVQMZAACCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4'-nitrophenyl)indole-2-carboxaldehyde 、 甘氨酸乙酯盐酸盐 在 sodium cyanoborohydride 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 3.25h， 以74%的产率得到ethyl N-[1-(4'-nitrophenyl)indol-2-ylmethyl]aminoacetate
  参考文献：
  名称：

  Chemical Confirmation of the Structure of a Mutagenic Aminophenylnorharman, 9-(4’-Aminophenyl)-9H-pyrido[3,4-b]indole: An Authentic Synthesis of 9-(4’-Nitrophenyl)-9H-pyrido[3,4-b]indole as Its Relay Compound

  摘要：

  9-(4'-Aminophenyl)-9H-pyrido[3,4-b]indole 2 is a mutagenic compound produced by non-mutagenic norharman 1 and aniline in the presence of S9 mix. 9-(4'-Nitrophenyl)-9H-pyrido[3,4-b]indole 4, the relay compound for synthesis of 2, was synthesized starting from ethyl indole-2-aldehyde 12 via initial N-(4-nitro)phenylation of the indole nucleus, elongation of the 2-aldehyde substituent, and then construction of the pyridine nucleus in order to ensure the nitrogen substitution in 2.

  DOI：

  10.3987/com-09-s(s)45
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 、 对氟硝基苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以51%的产率得到1-(4'-nitrophenyl)indole-2-carboxaldehyde
  参考文献：
  名称：

  Chemical Confirmation of the Structure of a Mutagenic Aminophenylnorharman, 9-(4’-Aminophenyl)-9H-pyrido[3,4-b]indole: An Authentic Synthesis of 9-(4’-Nitrophenyl)-9H-pyrido[3,4-b]indole as Its Relay Compound

  摘要：

  9-(4'-Aminophenyl)-9H-pyrido[3,4-b]indole 2 is a mutagenic compound produced by non-mutagenic norharman 1 and aniline in the presence of S9 mix. 9-(4'-Nitrophenyl)-9H-pyrido[3,4-b]indole 4, the relay compound for synthesis of 2, was synthesized starting from ethyl indole-2-aldehyde 12 via initial N-(4-nitro)phenylation of the indole nucleus, elongation of the 2-aldehyde substituent, and then construction of the pyridine nucleus in order to ensure the nitrogen substitution in 2.

  DOI：

  10.3987/com-09-s(s)45

文献信息

• Chemical Confirmation of the Structure of a Mutagenic Aminophenylnorharman, 9-(4’-Aminophenyl)-9H-pyrido[3,4-b]indole: An Authentic Synthesis of 9-(4’-Nitrophenyl)-9H-pyrido[3,4-b]indole as Its Relay Compound
  作者：Yasuoki Murakami、Nobuyuki Imai、Tsuyoshi Miura、Takashi Sugimura、Keiji Wakabayashi、Yukari Totsuka、Noriyasu Hada、Yuusaku Yokoyama、Hideharu Suzuki、Katsuyoshi Mitsunaga

  DOI：10.3987/com-09-s(s)45

  日期：——

  9-(4'-Aminophenyl)-9H-pyrido[3,4-b]indole 2 is a mutagenic compound produced by non-mutagenic norharman 1 and aniline in the presence of S9 mix. 9-(4'-Nitrophenyl)-9H-pyrido[3,4-b]indole 4, the relay compound for synthesis of 2, was synthesized starting from ethyl indole-2-aldehyde 12 via initial N-(4-nitro)phenylation of the indole nucleus, elongation of the 2-aldehyde substituent, and then construction of the pyridine nucleus in order to ensure the nitrogen substitution in 2.