3,8-Bis(acetylamino)-10H-quindoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,8-Bis(acetylamino)-10H-quindoline
• 英文别名: N-(3-acetamido-10H-indolo[3,2-b]quinolin-8-yl)acetamide
• 化学式: C₁₉H₁₆N₄O₂
• 分子量: 332.362
• InChiKey: ZGSIPZVHOSDLSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  86.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,8-Bis(acetylamino)-10H-quindoline 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以89%的产率得到10H-喹啉-3,8-二胺
  参考文献：
  名称：

  Structure Determination and Synthesis of Fluoro Nissl Green: An RNA-Binding Fluorochrome

  摘要：

  The isolation, structure determination, and total synthesis of Fluoro Nissl Green, a novel RNA-binding fluorochrome, are reported. Initially obtained: in only one part per 10(5), via a microwave-induced synthesis from m-phenylenediamine, the structure was determined by spectroscopic methods to be 3,8-diamino-10H-quindoline. The proposed structure was confirmed by a rational synthesis starting from m-phenylene diamine:and 2,4-dinitrobenzaldehyde. The key step employed a Friedlander reaction to construct the quindoline ring system from 1-acetyl-6-(acetylamino)-3-indolinone and 2-amino-4-(acetylamino)benzaldehyde. Histochemical studies with synthetic Fluoro Nissl Green demonstrate selective staining of neuronal perikarya and nucleoli.

  DOI：

  10.1021/jo00116a020
• 作为产物：
  描述：

  2-Amino-4-(acetylamino)benzaldehyde 、 1-Acetyl-6-(acetylamino)-3-indolinone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以49%的产率得到3,8-Bis(acetylamino)-10H-quindoline
  参考文献：
  名称：

  Structure Determination and Synthesis of Fluoro Nissl Green: An RNA-Binding Fluorochrome

  摘要：

  The isolation, structure determination, and total synthesis of Fluoro Nissl Green, a novel RNA-binding fluorochrome, are reported. Initially obtained: in only one part per 10(5), via a microwave-induced synthesis from m-phenylenediamine, the structure was determined by spectroscopic methods to be 3,8-diamino-10H-quindoline. The proposed structure was confirmed by a rational synthesis starting from m-phenylene diamine:and 2,4-dinitrobenzaldehyde. The key step employed a Friedlander reaction to construct the quindoline ring system from 1-acetyl-6-(acetylamino)-3-indolinone and 2-amino-4-(acetylamino)benzaldehyde. Histochemical studies with synthetic Fluoro Nissl Green demonstrate selective staining of neuronal perikarya and nucleoli.

  DOI：

  10.1021/jo00116a020

文献信息

• Structure Determination and Synthesis of Fluoro Nissl Green: An RNA-Binding Fluorochrome
  作者：Craig A. Merlic、Soheil Motamed、Bruce Quinn

  DOI：10.1021/jo00116a020

  日期：1995.6

  The isolation, structure determination, and total synthesis of Fluoro Nissl Green, a novel RNA-binding fluorochrome, are reported. Initially obtained: in only one part per 10(5), via a microwave-induced synthesis from m-phenylenediamine, the structure was determined by spectroscopic methods to be 3,8-diamino-10H-quindoline. The proposed structure was confirmed by a rational synthesis starting from m-phenylene diamine:and 2,4-dinitrobenzaldehyde. The key step employed a Friedlander reaction to construct the quindoline ring system from 1-acetyl-6-(acetylamino)-3-indolinone and 2-amino-4-(acetylamino)benzaldehyde. Histochemical studies with synthetic Fluoro Nissl Green demonstrate selective staining of neuronal perikarya and nucleoli.