1-Hydroxy-2-propyl-9,10-anthraquinone | 156334-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-Hydroxy-2-propyl-9,10-anthraquinone
• 英文别名: 1-Hydroxy-2-propylanthracene-9,10-dione
• CAS: 156334-29-1
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: TWAWHMMKFBHQLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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-propyl-9,10-anthraquinone 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 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-(4-hydroxy-2-nonenyloxy)-2-propyl-9,10-anthraquinone 以 甲醇 为溶剂， 反应 5.0h， 生成 1-Hydroxy-2-propyl-9,10-anthraquinone
  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

文献信息

• Observation of heavy atom effects in the development of water soluble caged 4-hydroxy-trans-2-nonenal
  作者：Paul B. Jones、Robert G. Brinson、Saurav J. Sarma、Salwa Elkazaz

  DOI：10.1039/b810954k

  日期：——

  anthraquinonyl chromophore to achieve water solubility, we studied the photochemistry of various substituents to understand their effect on the photochemistry. We observed a significant heavy atom effect that severely reduced the rate of oxidative cleavage of the alkoxy group. Based on the results of our substituent study, we designed a new caged 4-HNE that is soluble under physiological conditions, and

  在我们研究1-烷氧基-9,10-蒽醌的光化学过程中，我们开发了第二代笼状的4-羟基-反式-2-壬烯醛（4-HNE）。当我们优化蒽醌基生色团以达到水溶性时，我们研究了各种取代基的光化学，以了解它们对光化学的影响。我们观察到了显着的重原子效应，该效应严重降低了烷氧基的氧化裂解速率。根据我们对取代基的研究结果，我们设计了一种新的笼状4-HNE，该笼在生理条件下可溶，并且可以高产率光化学释放4-HNE。
• 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.
• Glucose Promoted Claisen Rearrangement of 1-Allyloxy Anthraquinones
  作者：Kadiyala V. S. N. Murty、Ranjan Pal、Kalyani Datta、Dipakranjan Mal

  DOI：10.1080/00397919408011730

  日期：1994.5

  Glucose effects the Claisen rearrangement of allyloxy anthraquinones at low temperatures(100-130-degrees-C).
• Caged <i>trans</i>-4-Hydroxy-2-nonenal
  作者：Robert G. Brinson、Paul B. Jones

  DOI：10.1021/ol048478l

  日期：2004.10.1

  (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.