1-((9,10-dioxo-1-oxanthracenyl)methyl)-18-crown-6 | 118921-90-7

• 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)-18-crown-6
• 英文别名: 1-(1,4,7,10,13,16-hexaoxacyclooctadec-2-ylmethoxy)anthracene-9,10-dione
• CAS: 118921-90-7
• 化学式: C₂₇H₃₂O₉
• 分子量: 500.546
• InChiKey: AIGRGYZQRZKIBR-UHFFFAOYSA-N

物化性质

• 沸点：
  704.7±60.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-((9,10-dioxo-1-oxanthracenyl)methyl)-18-crown-6 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-18-冠-6 在 sodium hydride 作用下， 生成 1-((9,10-dioxo-1-oxanthracenyl)methyl)-18-crown-6
  参考文献：
  名称：

  使用蒽醌衍生的套索醚和 podands 进行阳离子传输：电化学开启/关闭激活/失活的第一个例子

  摘要：

  蒽醌经历单电子和双电子还原以形成自由基阴离子或二价阴离子。当连接冠醚型大环或聚氧乙烯侧链时，还原的芳香族和氧供体基团协同结合阳离子。当蒽醌还原时，Li + 或Na + 的结合更大，因为它与阳离子之间存在电荷-电荷相互作用。该物业已用于方便运输。因此，源相的还原增强了阳离子的结合，而接收相的氧化诱导了阳离子的释放

  DOI：

  10.1021/ja00189a011

文献信息

• Carbon-oxygen bond-cleavage reactions by electron transfer. 4. Electrochemical and alkali-metal reductions of phenoxynaphthalenes
  作者：Todd A. Thornton、Gerald A. Ross、Dilip Patil、Kenichi Mukaida、Jeffrey O. Warwick、Neil F. Woolsey、Duane E. Bartak

  DOI：10.1021/ja00189a010

  日期：1989.3

  cleavage to produce phenol and naphthalene. The intermediacy of the naphthyl radical or the naphthyl anion in the reductive pathway was tested by the use of an intramolecular radical trap in the form of a 2-(3'-butenyl) substituent, i.e., 2-(3'-butenyl)-1-phenoxynaphthalene (3). Formation of 1-methylbenz(e)indan (4) upon the electrochemical reduction of 3 in the absence and presence of Dsub 2}O confirmed

  在 minus}2.42 和 minus}2.48 V vs SCE 观察到 1- (1) 和 2-苯氧基萘 (2) 还原为其各自的自由基阴离子。循环伏安法和计时电流法研究表明，两种自由基阴离子在干燥的 N,N-二甲基甲酰胺中的半衰期都大于 100 秒。醚的受控电位电解导致相对缓慢的区域选择性碳-氧键断裂以产生苯酚和萘。还原途径中萘基或萘基阴离子的中间体通过使用2-(3'-丁烯基)取代基，即2-(3'-丁烯基)-形式的分子内自由基阱来测试1-苯氧基萘 (3)。在不存在和存在 Dsub 2}O 的情况下通过电化学还原 3 形成 1-甲基苯 (e) 茚满 (4) 证实了 2-(3' -丁烯基)萘基自由基在自由基-阴离子裂解机制中。在四氢呋喃中用 Na/HMPA 还原苯氧基萘导致缓慢的区域选择性裂解，而用 Na-K 合金/四甘醇二甲醚还原使醚键定量裂解更快。通过在 Na-K 合金还原中通过
• 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。