2,7-dihydroxy-10-methylacridin-9(10H)one | 156644-25-6

• 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: 2,7-dihydroxy-10-methylacridin-9(10H)one
• 英文别名: 10-Methyl-2,7-dihydroxyacridan-9-one；2,7-dihydroxy-10-methyl-9-acridinone；2,7-Dihydroxy-10-methylacridin-9-one
• CAS: 156644-25-6
• 化学式: C₁₄H₁₁NO₃
• 分子量: 241.246
• InChiKey: QTFHLWJOOBVCHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,7-dihydroxy-10-methylacridin-9(10H)one 、 1,2-bis{2-[2-(2-tosylethoxy)ethoxy]ethoxy}benzene 在 四乙基氢氧化铵 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 以28%的产率得到[2,7-(10-methylacridin-9-one)]-(1',2'-phenyl)-29-crown-8
  参考文献：
  名称：

  Photoswitchable Macrocycles Incorporating Acridane Moieties

  摘要：

  合成了包含一个到三个9-苯基-芴啶单元的新型冠醚，产率适中。大环中的芴啶单元被转化为光活性的N-甲基-9-甲氧基-9-苯基-9,10-二氢芴啶（N-甲基-9-甲氧基-9-苯基芴啶）单元。

  DOI：

  10.1055/s-2007-990829
• 作为产物：
  描述：

  9-氯-2,7-二甲氧基吖啶 在 盐酸 、 sodium hydroxide 、 苄基三乙基氯化铵 、 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 114.0h， 生成 2,7-dihydroxy-10-methylacridin-9(10H)one
  参考文献：
  名称：

  Crown Ethers Derived from 2,7-Dihydroxyacridine and 2,7-Dihydroxyacridan-9-one

  摘要：

  We report the synthesis of nine acridine crown ethers 11a, 11b, 12a, 12b, 13a, 13b, 14b, 15b, and 16b having one or two acridine rings linked by poly(ethylene glycol) chains. Their H-1 and C-13 NMR spectra have been analyzed and the chemical shifts related to conformational aspects of the chain and to the tautomerism of the acridan-9-one ring. The transport rates have been determined for compounds 11b and 12b against a large variety of ions. While compound 11b is devoid of complexing properties, compound 12b transports Fe2+, Cu+, and Ag+ but not alkali-metal cations.

  DOI：

  10.1021/jo00097a016

文献信息

• Vichet Alain, Patellis Anne-Marie, Galy JeanPierre, Galy Anne-Marie, Barb+, J. Org. Chem, 59 (1994) N 18, S 5156-5161
  作者：Vichet Alain, Patellis Anne-Marie, Galy JeanPierre, Galy Anne-Marie, Barb+

  DOI：——

  日期：——
• Photoswitchable Macrocycles Incorporating Acridane Moieties
  作者：Werner Abraham、Marzena Orda-Zgadzaj

  DOI：10.1055/s-2007-990829

  日期：2007.11

  Novel crown ethers incorporating one to three 9-phenyl­acridinium units were synthesized in moderate yields. The acridinium units within the macrocycles were converted into the photoactive N-methyl-9-methoxy-9-phenyl-9,10-dihydroacridine (N-methyl-9-methoxy-9-phenylacridane) units.

  合成了包含一个到三个9-苯基-芴啶单元的新型冠醚，产率适中。大环中的芴啶单元被转化为光活性的N-甲基-9-甲氧基-9-苯基-9,10-二氢芴啶（N-甲基-9-甲氧基-9-苯基芴啶）单元。
• Crown Ethers Derived from 2,7-Dihydroxyacridine and 2,7-Dihydroxyacridan-9-one
  作者：Alain Vichet、Anne-Marie Patellis、Jean-Pierre Galy、Anne-Marie Galy、Jacques Barbe、Jose Elguero

  DOI：10.1021/jo00097a016

  日期：1994.9

  We report the synthesis of nine acridine crown ethers 11a, 11b, 12a, 12b, 13a, 13b, 14b, 15b, and 16b having one or two acridine rings linked by poly(ethylene glycol) chains. Their H-1 and C-13 NMR spectra have been analyzed and the chemical shifts related to conformational aspects of the chain and to the tautomerism of the acridan-9-one ring. The transport rates have been determined for compounds 11b and 12b against a large variety of ions. While compound 11b is devoid of complexing properties, compound 12b transports Fe2+, Cu+, and Ag+ but not alkali-metal cations.