1-hydroxy-2-octyl-9,10-anthraquinone | 90395-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-hydroxy-2-octyl-9,10-anthraquinone
• 英文别名: 1-hydroxy-2-octylanthraquinone；1-Hydroxy-2-octylanthracene-9,10-dione
• CAS: 90395-97-4
• 化学式: C₂₂H₂₄O₃
• 分子量: 336.431
• InChiKey: HXTGXHDAKMEYEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 1-hydroxy-2-octyl-9,10-anthraquinone 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 以603 mg的产率得到
  参考文献：
  名称：

  Facile synthesis of 1-butylamino- and 1,4-bis(butylamino)-2-alkyl-9,10-anthraquinone dyes for improved supercritical carbon dioxide dyeing

  摘要：

  Supercritical carbon dioxide (scCO(2)) has recently been conquering both material sciences and process engineering owing to its intriguing properties like high diffusivity and tuneable (de)solubilizing performance. However, except for impregnation with biocidal preservatives, utilization of scCO(2) for modification of wood including dyeing has been hitherto less explored. Therefore, we recently proposed a green wood dyeing approach that relies on the excellent carrier medium properties of CO2 for non-polar disperse dyes in supercritical conditions and their reversion when leaving the supercritical state. However, using a common disperse dye of the 9,10-anthraquinone family (Disperse Blue, DB-134) without the addition of co-solvent, only a moderate colour change was obtained for the interior of small wood cuboids (1 cm x 1 cm x 2 cm) even after extensive variation of scCO(2) process conditions. Insufficient solubility of the dye in scCO(2) was assumed to be a major hindrance for homogeneous wood dyeing. Therefore, we synthesized a variety of 1-n-butylamino- and 1,4-bis(n-butylamino)-9,10-anthraquinone derivatives carrying different alkyl moieties in 2-position, which was confirmed to improve scCO(2) solubility. Instead of a previously reported seven-step synthesis affording moderate yields only (60% on average), we propose an alternate much simpler synthesis comprising of Marschalk alkylation (2-position) and a sequence of tosylation and n-alkylamination (1-position). The latter proved to pave way to a wide variety of colours and disperse dyes of improved solubility in scCO(2). Moreover, all products were characterized by various techniques including liquid-state H-1 and C-13 NMR and X-ray crystallography. Complementing X-ray diffraction, quantum-mechanical simulations were performed to predict or confirm conformation and colour of selected compounds.

  DOI：

  10.1016/j.dyepig.2019.107991
• 作为产物：
  描述：

  正辛醛 、 1-羟基蒽醌 在 sodium dithionite 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以0.37 g的产率得到1-hydroxy-2-octyl-9,10-anthraquinone
  参考文献：
  名称：

  Facile synthesis of 1-butylamino- and 1,4-bis(butylamino)-2-alkyl-9,10-anthraquinone dyes for improved supercritical carbon dioxide dyeing

  摘要：

  Supercritical carbon dioxide (scCO(2)) has recently been conquering both material sciences and process engineering owing to its intriguing properties like high diffusivity and tuneable (de)solubilizing performance. However, except for impregnation with biocidal preservatives, utilization of scCO(2) for modification of wood including dyeing has been hitherto less explored. Therefore, we recently proposed a green wood dyeing approach that relies on the excellent carrier medium properties of CO2 for non-polar disperse dyes in supercritical conditions and their reversion when leaving the supercritical state. However, using a common disperse dye of the 9,10-anthraquinone family (Disperse Blue, DB-134) without the addition of co-solvent, only a moderate colour change was obtained for the interior of small wood cuboids (1 cm x 1 cm x 2 cm) even after extensive variation of scCO(2) process conditions. Insufficient solubility of the dye in scCO(2) was assumed to be a major hindrance for homogeneous wood dyeing. Therefore, we synthesized a variety of 1-n-butylamino- and 1,4-bis(n-butylamino)-9,10-anthraquinone derivatives carrying different alkyl moieties in 2-position, which was confirmed to improve scCO(2) solubility. Instead of a previously reported seven-step synthesis affording moderate yields only (60% on average), we propose an alternate much simpler synthesis comprising of Marschalk alkylation (2-position) and a sequence of tosylation and n-alkylamination (1-position). The latter proved to pave way to a wide variety of colours and disperse dyes of improved solubility in scCO(2). Moreover, all products were characterized by various techniques including liquid-state H-1 and C-13 NMR and X-ray crystallography. Complementing X-ray diffraction, quantum-mechanical simulations were performed to predict or confirm conformation and colour of selected compounds.

  DOI：

  10.1016/j.dyepig.2019.107991

文献信息

• The Alkylation of 1-Hydroxyanthraquinone with Visible-light Irradiation
  作者：Masahiro Tajima、Haruo Inoue、Mitsuhiko Hida

  DOI：10.1246/bcsj.57.305

  日期：1984.1

  The 2-position of 1-hydroxyanthraquinone was alkylated by the use of tertiary amine or methanol with visible-light irradiation (λ>400 nm).

  在可见光照射（λ>400 nm）下，使用叔胺或甲醇对 1-羟基蒽醌的 2-位进行烷基化。
• TAJIMA, MASAHIRO;INOUE, HARUO;HIDA, MITSUHIKO, BULL. CHEM. SOC. JAP., 1984, 57, N 1, 305-306
  作者：TAJIMA, MASAHIRO、INOUE, HARUO、HIDA, MITSUHIKO

  DOI：——

  日期：——
• Facile synthesis of 1-butylamino- and 1,4-bis(butylamino)-2-alkyl-9,10-anthraquinone dyes for improved supercritical carbon dioxide dyeing
  作者：Julien Jaxel、Hassan Amer、Markus Bacher、Alexander Roller、Matthias Guggenberger、Nele Sophie Zwirchmayr、Christian Hansmann、Falk Liebner

  DOI：10.1016/j.dyepig.2019.107991

  日期：2020.2

  Supercritical carbon dioxide (scCO(2)) has recently been conquering both material sciences and process engineering owing to its intriguing properties like high diffusivity and tuneable (de)solubilizing performance. However, except for impregnation with biocidal preservatives, utilization of scCO(2) for modification of wood including dyeing has been hitherto less explored. Therefore, we recently proposed a green wood dyeing approach that relies on the excellent carrier medium properties of CO2 for non-polar disperse dyes in supercritical conditions and their reversion when leaving the supercritical state. However, using a common disperse dye of the 9,10-anthraquinone family (Disperse Blue, DB-134) without the addition of co-solvent, only a moderate colour change was obtained for the interior of small wood cuboids (1 cm x 1 cm x 2 cm) even after extensive variation of scCO(2) process conditions. Insufficient solubility of the dye in scCO(2) was assumed to be a major hindrance for homogeneous wood dyeing. Therefore, we synthesized a variety of 1-n-butylamino- and 1,4-bis(n-butylamino)-9,10-anthraquinone derivatives carrying different alkyl moieties in 2-position, which was confirmed to improve scCO(2) solubility. Instead of a previously reported seven-step synthesis affording moderate yields only (60% on average), we propose an alternate much simpler synthesis comprising of Marschalk alkylation (2-position) and a sequence of tosylation and n-alkylamination (1-position). The latter proved to pave way to a wide variety of colours and disperse dyes of improved solubility in scCO(2). Moreover, all products were characterized by various techniques including liquid-state H-1 and C-13 NMR and X-ray crystallography. Complementing X-ray diffraction, quantum-mechanical simulations were performed to predict or confirm conformation and colour of selected compounds.