2-benzyl-1-hydroxy-9,10-anthraquinone | 54454-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-benzyl-1-hydroxy-9,10-anthraquinone
• 英文别名: 2-benzyl-1-hydroxy-anthraquinone；2-Benzyl-1-hydroxy-anthrachinon；2-Benzyl-1-hydroxyanthracene-9,10-dione
• CAS: 54454-84-1
• 化学式: C₂₁H₁₄O₃
• 分子量: 314.34
• InChiKey: ASLVBISTDOYLLH-UHFFFAOYSA-N

物化性质

• 沸点：
  526.1±39.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  2-benzyl-1-hydroxy-9,10-anthraquinone 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 生成 2-Benzyl-1-[[4-(1,3-dioxolan-2-yl)phenyl]-methoxymethoxy]anthracene-9,10-diol
  参考文献：
  名称：

  Photochemistry of 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones in methanol: A facile process for the preparation of aldehydes and ketones

  摘要：

  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.

  DOI：

  10.1021/jo00126a040
• 作为产物：
  描述：

  1-<<<4-(1,3-Dioxolan-2-yl)>benzyl>oxy>-2-benzyl-9,10-anthraquinone 在 air 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2-benzyl-1-hydroxy-9,10-anthraquinone
  参考文献：
  名称：

  Photochemistry of 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones in methanol: A facile process for the preparation of aldehydes and ketones

  摘要：

  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.

  DOI：

  10.1021/jo00126a040

文献信息

• Photochemistry of 1,<i>n</i>-Dibenzyloxy-9,10-anthraquinones
  作者：Saurav J. Sarma、Paul B. Jones

  DOI：10.1021/jo100650u

  日期：2010.6.4

  favored reaction pathway shifting with minor changes in substitution on the anthraquinone. Several types of product require cleavage of the C−O bond on the benzyloxy group and, apparently, follow a photo-Claisen-type mechanism. Others involve the expected 1,5-diradical but do not exhibit the single-electron transfer usually observed in the Blankespoor-type reaction. The results indicate the importance

  研究了一系列具有多个苄氧基取代基的9,10-蒽醌的光化学性质。在极性溶剂中，预期的Blankespoor氧化裂解反应是主要的反应途径，但在大多数情况下，观察到一些次要产物。在非极性溶剂中，这些次要产物的丰度急剧增加。观察到四种类型的产物，其有利的反应路径发生了变化，蒽醌上的取代发生了微小变化。几种类型的产品需要裂解苄氧基上的C-O键，并且显然遵循光克莱森型机理。其他涉及预期的1，5-双自由基，但不表现出通常在布兰克斯珀型反应中观察到的单电子转移。
• Short-Lived 1,5-Biradicals Formed from Triplet 1-Alkoxy- and 1-(Benzyloxy)-9,10-anthraquinones
  作者：Robert P. Smart、Timothy J. Peelen、Ronald L. Blankespoor、Donald L. Ward

  DOI：10.1021/ja962633c

  日期：1997.1.1

  corresponding aldehyde, trans-(2-phenylcyclopropyl)carboxaldehyde. In addition, products resulting from rearrangement of the 1,5-biradical to a homoallylic 1,8-biradical were also obtained. Using the known rate constant for the rearrangement of the phenylcyclopropylmethyl radical to the homoallylic radical and the obse...

  环丙基甲基和（反式-2-苯基环丙基）甲基自由基时钟用于估计由取代的 1-烷氧基-9,10-蒽醌通过光激发和随后的 1,5-氢原子转移形成的三线态双自由基的寿命。1-（环丙基甲氧基）-2-甲基-9,10-蒽醌（1cp）在氩气净化的甲醇中的辐照（350 nm）产生主要的蒽氢醌产物（2）。暴露在空气中后，2 迅速转化为环丙烷甲醛和 1-羟基-2-X-9,10-蒽醌 (3)。相比之下，在类似条件下照射 1-(trans-2-phenylcyclopropyl)methoxy}-2-benzyl-9,10-anthraquinone (1pcp) 只产生少量的 3 和相应的醛，反式-（2-苯基环丙基） ) 甲醛。此外，由 1,5-双基重排为同位烯丙基 1 产生的产物，还获得了8-双自由基。使用已知的速率常数将苯基环丙基甲基基团重排为高烯丙基基团和 ob...
• Accumulation in Dasuopu ice core in Qinghai-Tibet Plateau and solar activity
  作者：Keqin Duan、Ninglian Wang、Yuefang Li、Weizheng Sun

  DOI：10.1007/bf02884987

  日期：2000.6

  The time series of accumulation in recent 300 years correlated well with solar activity in Dasuopu ice core. Results of spectrum analysis on the accumulation time series of the Dasuopu ice core shows that there are some periods that coincide with the periods of solar activity. By comparing the long-time change trend of the accumulation in the Dasuopu ice core with various kinds of indexes of solar activity intensity, a negative correlation is found between the trend and solar activity.
• Novel anthraquinone inhibitors of human leukocyte elastase and cathepsin G
  作者：David E. Zembower、Chih Min Kam、James C. Powers、Leon H. Zalkow

  DOI：10.1021/jm00087a014

  日期：1992.5

  A large series of variously substituted anthraquinones has been synthesized and assayed for inhibitory capacity against human leukocyte elastase (HLE) and cathepsin G (CatG), two serine proteinases implicated in diseases characterized by the abnormal degradation of connective tissue, such as pulmonary emphysema and rheumatoid arthritis. It was found that 2-alkyl-1,8-dihydroxyanthraquinone analogues are competitive inhibitors of HLE with IC50 values ranging from 4 to 10-mu-M, and also inhibit CatG with IC50 values ranging from 25 to 55-mu-M. Consequently, analogues containing the 2-alkyl-1-hydroxy-8-methoxyanthraquinone substitution pattern inhibit HLE to the same magnitude as for the compounds above, but show very little inhibition of CatG. Anthraquinones containing long, hydrophobic n-butyl carbonate moieties in the 1- and 8-positions in conjunction with a third hydrophobic substituent in the 2- or 3-position are highly selective for HLE, with K(i) values in the range of 10(-7) M. All of the inhibitors described are completely reversible, with no evidence of acyl-enzyme formation detected.
• DE583871
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  公开号：——

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