1-((9,10-dioxo-1-oxanthracenyl)methyl)-15-crown-5 | 104084-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-((9,10-dioxo-1-oxanthracenyl)methyl)-15-crown-5
• 英文别名: 1-((1-oxaanthracene-9,10-dione)methyl)-15-crown-5；1-(1,4,7,10,13-Pentaoxacyclopentadec-2-ylmethoxy)anthracene-9,10-dione
• CAS: 104084-69-7
• 化学式: C₂₅H₂₈O₈
• 分子量: 456.493
• InChiKey: ISMYRVVBVJXXKO-UHFFFAOYSA-N

物化性质

• 沸点：
  668.3±55.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-((9,10-dioxo-1-oxanthracenyl)methyl)-15-crown-5 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-Butoxy-9,10-anthraquinone
  参考文献：
  名称：

  Alkynes and poly(ethylene glycol) derivatives as nucleophiles and catalysts in substitution reactions of 1-chloroanthraquinones

  摘要：

  Two synthetically useful approaches to 1-substituted anthraquinone derivatives are reported. Application of these methods afforded the following 1-anthraquinyl ethers: n-propyl, n-butyl, n-octyl, n-nonyl, n-hexadecyl, isoamyl, allyl, 2-butenyl, (E)-2-hexenyl, (E)-2-tridecyl, benzyl, phenyl, 4-methylphenyl, 2-butynyl, 2-pentynyl, 2-hexynyl, 3-pentynyl, 3-hexynyl, 3-heptynyl, 3-nonynyl, 4-hexynyl, 4-heptynyl, 5-heptynyl, 5-octynyl, 5-nonynyl, 2-methoxyethyl, 2-(2-methoxyethoxy)ethyl, 2-[2-[2-(octadecyloxy)ethoxy]ethoxy]ethyl, 2-(methylthio)ethyl, 2-(1-piperidino)ethyl, and 2-(1-morpholino)ethyl. The results of about 100 nucleophilic substitution reactions (a number were duplicates) are presented. Most of these reactions involve either a new approach, new products, or both. Included are displacements of chloride by alkanols, alkenols, and alkynols. Of the three, only the latter afford acceptable yields of product, although lower yields are observed as the distance between hydroxyl and triple bond increases. Nucleophiles of the type RO(CH2CH2O)nOH proved remarkably effective. Alkynyl ethers and poly(oxyethylene) ethers also proved to be excellent leaving groups. Both alkynols and oligoethylene glycol monoethers were found to be catalysts for the conversion of 1-chloroanthraquinone into 1-anthraquinyl ethers. In an attempt to understand the mechanism of this reaction, solid-state structures of four anthraquinone derivatives have been obtained. These have poly(ethyleneoxy), morpholino, or alkynyl side arms.

  DOI：

  10.1021/jo00025a021
• 作为产物：
  描述：

  1-氯蒽醌 、 2-羟甲基-15-冠-5 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以40%的产率得到1-((9,10-dioxo-1-oxanthracenyl)methyl)-15-crown-5
  参考文献：
  名称：

  蒽醌取代的碳枢轴套索醚和豆荚中的电化学开关：几何和电子协同中的链长效应

  摘要：

  Synthese d'une serie d'anthraquinones substituees en -1 (ou Ar) par le substituant E=−CH 2 CH 2 - avec 形成 d'Ar-OCH 3 , Ar-OEOEOCH 3 , Ar-OEOEOEOCH 3 , Ar-OEOEOEOCH 3 ，Ar-OEOEOEOEOEOCH 3 ，Ar-OEOEOEO-Ar 和 d'Ar-O-CH 2 -15-crown-5。Mise en evidence de l'existence de Couples redox a un ou 2 electrons (voltammetrie cyclique) dans le cas des differents systemes lors de l'addition d'ions Li + , Na + et K +

  DOI：

  10.1021/ja00284a019

文献信息

• The remarkable nucleophilic substitutions of anthraquinones using podands as nucleophiles and leaving groups
  作者：Kim Yoo Hyunsook、Dawn M. Davis、Chen Zhihong、Luis Echegoyen、George W. Gokel

  DOI：10.1016/s0040-4039(00)94332-6

  日期：——

  Nucleophilic aromatic substitution reactions between saturated alcohols and 1-chloroanthraquinones are generally poor but high yields are obtained when polyethylene glycol monomethyl ethers are used as nucleophiles or when an alcohol is the nucleophiles and the podand is the leaving group.

  饱和醇和1-氯蒽醌之间的亲核芳族取代反应通常较差，但当使用聚乙二醇单甲醚作为亲核试剂或以醇为亲核试剂且podand为离去基团时，收率较高。
• Electrochemical switching of lariat ethers: enhanced cation binding by one- and two-electron reduction of an anthraquinone sidearm
  作者：Luis Echegoyen、Deborah A. Gustowski、Vincent J. Gatto、George W. Gokel

  DOI：10.1039/c39860000220

  日期：——

  The first example of cation binding enhancement by electrochemical switching in a lariat ether, accomplished by one- or two-electron reduction of a quinone sidearm, is presented.

  提出了通过在套索状醚中进行电化学转换来增强阳离子结合力的第一个例子，该反应通过醌侧臂的一电子或二电子还原来实现。