1-(prop-2'-enyloxy)anthraquinone | 64302-83-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(prop-2'-enyloxy)anthraquinone
• 英文别名: 1-allyloxy-9,10-anthraquinone；1-(Allyloxy)anthraquinone；1-(Prop-2-enyloxy)-anthrachinon；1-Allyloxyanthrachinon；1-Allyloxy-anthraquinone；1-prop-2-enoxyanthracene-9,10-dione
• CAS: 64302-83-6
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: QPOGWPCQSCKPCP-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  446.0±34.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(prop-2'-enyloxy)anthraquinone 在 palladium on activated charcoal 葡萄糖 、 四丁基氟化铵 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 13.83h， 生成 2-((E)-3-Hydroxy-oct-1-enyl)-11b-methoxy-4-propyl-11bH-1,3-dioxa-benzo[de]anthracen-7-one
  参考文献：
  名称：

  Caged trans-4-Hydroxy-2-nonenal

  摘要：

  (GRAPHICS)A caged 4-hydroxy-2-nonenal (4-HNE) has been prepared and its photochemistry investigated. Upon photolysis, 1 releases 4-HNE in up to 100% yield. From these photolyses, 4-HNE could be isolated in up to 91% yield. 4-HNE is produced under either aerobic or anaerobic conditions. The caging strategy does not require prior preparation of 4-HNE and, therefore, represents a three-step synthetic route to the bioactive enal in 48% overall yield.

  DOI：

  10.1021/ol048478l
• 作为产物：
  描述：

  1-氯蒽醌 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-(prop-2'-enyloxy)anthraquinone
  参考文献：
  名称：

  使用Podands作为亲核试剂和离去基团对蒽醌进行非凡的亲核取代

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)94332-6

文献信息

• Efficient reductive Claisen rearrangement of prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones with iron powder in ionic liquids
  作者：Nadali, Samaneh、Khoshroo, Ali、Aghapour, Ghasem

  DOI：10.3906/kim-1711-49

  日期：——

  A rapid and selective iron-mediated reductive Claisen rearrangement of various prop-2'-enyloxyanthraquinones and 2'-chloroprop-2'-enyloxyanthraquinones to 1-hydroxy-2-(prop-2'-enyl)anthraquinones and anthrafurandiones is presented. All reactions are carried out in a mixture of ionic liquids, [Bzmim]Cl (1-benzyl-3-methylimidazolium chloride) and [Hmim]BF$_4}$ (1-methylimidazolium tetrafluoroborate), in short reaction times (5-35 min). Our study showed that 1-(prop-2'-enyloxy)anthraquinone is more active than 1-(2'-chloroprop-2'-enyloxy)anthraquinone to perform this rearrangement.

  本研究介绍了铁介导的各种丙-2'-烯氧基蒽醌和 2'-氯丙-2'-烯氧基蒽醌到 1-羟基-2-(丙-2'-烯基)蒽醌和蒽呋喃酮的快速和选择性还原性克莱森重排反应。 所有反应均在离子液体[Bzmim]Cl（1-苄基-3-甲基咪唑氯化物）和[Hmim]BF$_4}$（1-甲基咪唑四氟硼酸盐）的混合物中进行，反应时间短（5-35 分钟）。我们的研究表明，1-(丙-2'-烯氧基)蒽醌比 1-(2'-氯丙-2'-烯氧基)蒽醌在进行这种重排反应时更为活跃。
• Reductive claisen rearrangements of anthraquinone allyl ethers
  作者：Ian K. Boddy、J. Boniface、Richard C. Cambie、Peter A. Craw、David S. Larsen、Hamish McDonald、Peter S. Rutledge、Paul D. Woodgate

  DOI：10.1016/s0040-4039(00)85614-2

  日期：1982.1

  Gentle heating of allyloxyanthraquinones with sodium dithionite in dimethylformanide - water effects a rapid and controlled rearrangement to give high yields of 2-allyanthraquinones.

  将二甲基甲酰胺-水中的连二亚硫酸钠与烯丙氧基蒽醌温和加热，可快速而受控地进行重排，从而获得高产率的2-烯丙基蒽醌。
• 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.
• Boddy, Ian K.; Boniface, Peter J.; Cambie, Richard C., Australian Journal of Chemistry, 1984, vol. 37, # 7, p. 1511 - 1529
  作者：Boddy, Ian K.、Boniface, Peter J.、Cambie, Richard C.、Craw, Peter A.、Huang, Zhen-Dong、et al.

  DOI：——

  日期：——
• Claisen Rearrangement of Allyloxyanthraquinones with Silver/Potassium Iodide in Acetic Acid as a New and Efficient Reagent
  作者：Hashem Sharghi、Ghasem Aghapour

  DOI：10.1021/jo991674z

  日期：2000.5.1