1-Hydroxy-2-butyl-9,10-anthraquinone | 131559-12-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Hydroxy-2-butyl-9,10-anthraquinone
• 英文别名: 2-Butyl-1-hydroxyanthra-9,10-quinone；2-butyl-1-hydroxyanthracene-9,10-dione
• CAS: 131559-12-1
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: SBDRWPLVXGADSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  1-Hydroxy-2-butyl-9,10-anthraquinone 在 吡啶 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 120.0h， 生成 2-丁基-1-丁基氨基蒽醌
  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：

  1,2-二羟基蒽醌 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1-Hydroxy-2-butyl-9,10-anthraquinone
  参考文献：
  名称：

  钯催化三氟甲基苯磺酸与锡烷的偶联反应合成蒽醌衍生物。

  摘要：

  钯催化的羟基蒽醌三氟甲磺酸酯与锡烷的偶联可在中性条件下有效地取代羟基蒽醌。

  DOI：

  10.1016/s0040-4039(00)97839-0

文献信息

• Photochemistry of 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones in methanol: A facile process for the preparation of aldehydes and ketones
  作者：Ronald L. Blankespoor、Robert P. Smart、Eric D. Batts、Alan A. Kiste、Rebecca E. Lew、Marc E. Van der Vliet

  DOI：10.1021/jo00126a040

  日期：1995.10

  The facile production of acid sensitive aldehydes and ketones via photochemical intramolecular delta-hydrogen atom transfer in 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones (1) was investigated. Irradiation of 1 in argon purged methanol generates the primary photoproducts, 1-(RCH(OMe)O)-and 1-(ArCH(OMe)O)-9,10-antharahydroquinones (2), respectively. Upon exposure to air, the intermediate anthrahydroquinone is rapidly converted to the corresponding aldehyde and 1-hydroxy-9,10-anthraquinone (3), which can be recycled. Aldehydes containing an acetal or ketal were prepared in high yields using this photoprocess. Apparent rate constants for the photodemethylation of 1-methoxy-2-X-9,10-anthraquinones (X = H, Me, Et, Pr, Bu, i-Bu, and benzyl) were measured and found to vary by a factor of 10 separating the slowest anthraquinone (X = H) and the fastest (X = benzyl), indicating a strong dependency upon the size of the substituent at the a-position. These rate constants are ascribed to equilibrium populations of confonmers in the geometry required for reaction in the n,pi* triplet state.
• Photochemical Synthesis of 3-Alkynals from 1-Alkynoxy-9,10-anthraquinones
  作者：Ronald L. Blankespoor、Peter J. Boldenow、Eric C. Hansen、Jeffrey M. Kallemeyn、Andrew G. Lohse、David M. Rubush、Derek Vrieze

  DOI：10.1021/jo900298y

  日期：2009.5.15

  Photolysis of 1-(3-alkynoxy)-9,10-anthraquinones in deoxygenated methanol leads to moderate yields (35-45%) of 3-alkynals along with the unexpected formation of diacetals. Reaction of these 3-alkynals with Grignard and Wittig reagents occurs nearly quantitatively without rearrangement to their 2,3-dienal isomers.
• TAMAYO, NURIA;ECHAVARREN, ANTONIO M.;PAREDES, M. CARMEN;FARINA, FRANCISCO+, TETRAHEDRON LETT., 31,(1990) N6, C. 5189-5192
  作者：TAMAYO, NURIA、ECHAVARREN, ANTONIO M.、PAREDES, M. CARMEN、FARINA, FRANCISCO+

  DOI：——

  日期：——
• Synthesis of anthraquinone derivatives by palladium-catalyzed coupling of triflates with stannanes.
  作者：Nuria Tamayo、Antonio M. Echavarren、M. Carmen Paredes、Francisco Fariña、Pedro Noheda

  DOI：10.1016/s0040-4039(00)97839-0

  日期：1990.1

  The palladium-catalyzed coupling of hydroxyanthraquinone triflates with stannanes provides an efficient entry into substituted anthraquinones under neutral conditions.

  钯催化的羟基蒽醌三氟甲磺酸酯与锡烷的偶联可在中性条件下有效地取代羟基蒽醌。
• 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.