3-n-hexyl-1H-cinnolin-4-one | 1342948-22-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-n-hexyl-1H-cinnolin-4-one
• 英文别名: 3-hexyl-1H-cinnolin-4-one
• CAS: 1342948-22-4；664321-92-0
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: XKTXGKWPMXLJNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-n-hexyl-1H-cinnolin-4-one 在 盐酸 、 tin 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 0.25h， 以70%的产率得到3-n-hexyl-1,4-dihydro-cinnoline
  参考文献：
  名称：

  A convenient and efficient protocol for the synthesis of 4(1H)-cinnolones, 1,4-dihydrocinnolines, and cinnolines in aqueous medium: application for detection of nitrite ions

  摘要：

  3-Aryl/alkyl-4(1H)-cinnolones are obtained in one step from 2-aryl/alkylethynyl aniline by reaction with sodium nitrite and dilute hydrochloric acid via Richter cyclization. The alkyl cinnolones on reduction with Sn/HCl furnish 1,4-dihydro-3-alkylcinnolines, which are converted to 3-alkylcinnolines by treatment with NaNO2/HCl/KI. The whole process is carried out in aqueous medium at ambient temperature within a short reaction period. The reaction of 2-phenylethynyl aniline exhibits yellow color with UV absorbance at 391 nm and has been successfully tested for the detection of nitrite ions in water at parts per million concentration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.016
• 作为产物：
  描述：

  2-(oct-1-yn-1-yl)aniline 在 盐酸 、 水 、 sodium nitrite 作用下， 反应 0.17h， 以83%的产率得到3-n-hexyl-1H-cinnolin-4-one
  参考文献：
  名称：

  A convenient and efficient protocol for the synthesis of 4(1H)-cinnolones, 1,4-dihydrocinnolines, and cinnolines in aqueous medium: application for detection of nitrite ions

  摘要：

  3-Aryl/alkyl-4(1H)-cinnolones are obtained in one step from 2-aryl/alkylethynyl aniline by reaction with sodium nitrite and dilute hydrochloric acid via Richter cyclization. The alkyl cinnolones on reduction with Sn/HCl furnish 1,4-dihydro-3-alkylcinnolines, which are converted to 3-alkylcinnolines by treatment with NaNO2/HCl/KI. The whole process is carried out in aqueous medium at ambient temperature within a short reaction period. The reaction of 2-phenylethynyl aniline exhibits yellow color with UV absorbance at 391 nm and has been successfully tested for the detection of nitrite ions in water at parts per million concentration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.016

文献信息

• A convenient and efficient protocol for the synthesis of 4(1H)-cinnolones, 1,4-dihydrocinnolines, and cinnolines in aqueous medium: application for detection of nitrite ions
  作者：Raju Dey、Brindaban C. Ranu

  DOI：10.1016/j.tet.2011.09.016

  日期：2011.11

  3-Aryl/alkyl-4(1H)-cinnolones are obtained in one step from 2-aryl/alkylethynyl aniline by reaction with sodium nitrite and dilute hydrochloric acid via Richter cyclization. The alkyl cinnolones on reduction with Sn/HCl furnish 1,4-dihydro-3-alkylcinnolines, which are converted to 3-alkylcinnolines by treatment with NaNO2/HCl/KI. The whole process is carried out in aqueous medium at ambient temperature within a short reaction period. The reaction of 2-phenylethynyl aniline exhibits yellow color with UV absorbance at 391 nm and has been successfully tested for the detection of nitrite ions in water at parts per million concentration. (C) 2011 Elsevier Ltd. All rights reserved.