1-Propoxyanthraquinone | 81386-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Propoxyanthraquinone
• 英文别名: 1-Propoxyanthracene-9,10-dione
• CAS: 81386-67-6
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: BHJAPOHJYIWVPK-UHFFFAOYSA-N

物化性质

• 熔点：
  151.5-152 °C(Solv: hexane (110-54-3))
• 沸点：
  446.9±34.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.25
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-Propoxyanthraquinone 在 哌啶 、 sodium hydroxide 、 sodium dithionite 、 对甲苯磺酰叠氮 作用下， 生成 10-Diazonio-4-propoxyanthracen-9-olate
  参考文献：
  名称：

  1-烷氧基蒽醌的分子内反应性。卡宾衍生的1,5-双自由基的歧化作用（SET）

  摘要：

  苯中的1-烷氧基-9-重氮蒽酮12的光解会引起侧链中氢的提取，然后使中间的双基20环化（→15→16）或歧化（→17 + 18）。在醇，还原三重anthronylidenes（的3 14→21→22）竞争与地层的20，和分子内电子转移20根引线最终缩醛24。

  DOI：

  10.1016/s0040-4039(98)01398-7
• 作为产物：
  描述：

  1-羟基-9,9-二甲氧基-10-蒽酮 在 盐酸 、 氢氧化钾 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 0.67h， 生成 1-Propoxyanthraquinone
  参考文献：
  名称：

  Popov, S. I.; Volosenko, V. P., Journal of Organic Chemistry USSR (English Translation), 1982, p. 127 - 131

  摘要：

  DOI：

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。
• Alkynes and poly(ethylene glycol) derivatives as nucleophiles and catalysts in substitution reactions of 1-chloroanthraquinones
  作者：Jun Ping Fang、Tianbao Lu、Hyunsook Kim、Isaura Delgado、Philippe Geoffroy、Jerry L. Atwood、George W. Gokel

  DOI：10.1021/jo00025a021

  日期：1991.12

  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.
• Podand-catalyzed nucleophilic aromatic substitutions of anthraquinones: a novel synthetic approach and a mechanistic suggestion from solid-state data
  作者：Tianbao Lu、Hyunsook Kim Yoo、Hongming Zhang、Simon Bott、Jerry L. Atwood、Luis Echegoyen、George W. Gokel

  DOI：10.1021/jo00295a001

  日期：1990.4
• HYUNSOOK, KIM YOO;DAVIS, DAWN M.;CHEN, ZHIHONG;ECHEGOYEN, LUIS;GOKEL, GEO+, TETRAHEDRON LETT., 31,(1990) N, C. 55-58
  作者：HYUNSOOK, KIM YOO、DAVIS, DAWN M.、CHEN, ZHIHONG、ECHEGOYEN, LUIS、GOKEL, GEO+

  DOI：——

  日期：——
• LU, TIANBAO;YOO, HYUNSOOK KIM;ZHANG, HONGMING;BOTT, SIMON;ATWOOD, JERRY L+, J. ORG. CHEM., 55,(1990) N, C. 2269-2270
  作者：LU, TIANBAO、YOO, HYUNSOOK KIM、ZHANG, HONGMING、BOTT, SIMON、ATWOOD, JERRY L+

  DOI：——

  日期：——