10-methyl-4-[(2S,12S)-2,12-dimethyl-1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-ylmethyl]acridin-9(10H)-one | 1207460-12-5

• 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: 10-methyl-4-[(2S,12S)-2,12-dimethyl-1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-ylmethyl]acridin-9(10H)-one
• 英文别名: 4-[[(2S,12S)-2,12-dimethyl-1,4,7,10,13-pentaoxa-16-azacyclooctadec-16-yl]methyl]-10-methylacridin-9-one
• CAS: 1207460-12-5
• 化学式: C₂₉H₄₀N₂O₆
• 分子量: 512.646
• InChiKey: ZNSWGZAWJQVUGD-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2S,12S)-2,12-dimethyl-1,4,7,10,13-pentaoxa-16-azacyclooctadecane 、 4-chloromethyl-10-methylacridin-9(10H)-one 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以37%的产率得到10-methyl-4-[(2S,12S)-2,12-dimethyl-1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-ylmethyl]acridin-9(10H)-one
  参考文献：
  名称：

  Synthesis and optical characterization of novel azacrown ethers containing an acridinone or an N-methylacridinone unit as potential fluorescent chemosensors

  摘要：

  Four new achiral and four new chiral monoazacrown ethers containing an acridinone or an N-methylacridinone fluorescent signalling unit were prepared by reacting chloromethyl-substituted acridinone derivatives with achiral monoazacrown ethers with different cavity sizes and enantiopure monoaza-18-crown-6 ethers having two methyl and two isobutyl groups on their chiral centres, respectively. The operation of these chemosensors is based on the photoinduced electron transfer (PET) process, thus they show fluorescence enhancement in the presence of cationic guests. Their fluorescent behaviour as well as their complexation properties towards selected metal ions and the enantiomers of alpha-(1-naphthyl)-ethylammonium perchlorate and potassium mandelate were examined. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.10.076

文献信息

• Synthesis and optical characterization of novel azacrown ethers containing an acridinone or an N-methylacridinone unit as potential fluorescent chemosensors
  作者：Ildikó Móczár、Péter Huszthy、András Mezei、Mihály Kádár、József Nyitrai、Klára Tóth

  DOI：10.1016/j.tet.2009.10.076

  日期：2010.1

  Four new achiral and four new chiral monoazacrown ethers containing an acridinone or an N-methylacridinone fluorescent signalling unit were prepared by reacting chloromethyl-substituted acridinone derivatives with achiral monoazacrown ethers with different cavity sizes and enantiopure monoaza-18-crown-6 ethers having two methyl and two isobutyl groups on their chiral centres, respectively. The operation of these chemosensors is based on the photoinduced electron transfer (PET) process, thus they show fluorescence enhancement in the presence of cationic guests. Their fluorescent behaviour as well as their complexation properties towards selected metal ions and the enantiomers of alpha-(1-naphthyl)-ethylammonium perchlorate and potassium mandelate were examined. (C) 2009 Elsevier Ltd. All rights reserved.