4-demethoxy-7,9-dideoxydaunomycinone | 67122-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 4-demethoxy-7,9-dideoxydaunomycinone
• 英文别名: 8-Acetyl-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione
• CAS: 67122-26-3
• 化学式: C₂₀H₁₆O₅
• 分子量: 336.344
• InChiKey: HIIVCLZCYLLSFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-demethoxy-7,9-dideoxydaunomycinone 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 potassium tert-butylate 、 氧气 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 亚磷酸三乙酯 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 18.5h， 生成 (7S,9S)9-乙酰基-7,8,9,10-四氢-6,7,9,11-四羟基-5,12-并四苯二酮
  参考文献：
  名称：

  Facile Total Syntheses of Idarubicinone‐7‐β‐D‐glucuronide: Convenient Preparations of AB‐Ring Synthon Using Some Carboxylic Acid Derivatives

  摘要：

  Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (+/-)-idarubicinone 3b by general methods. Esterification of (+/-)-3b with (S)-(+)-O-acetylmandelic acid with subsequent separation and deprotection gave (+)-3b and (-)-3b. Reaction of separated two stereoisomers with acetobromo-alpha-D-glucuronic acid methyl ester respective followed by hydrolysis using lithium hydroxide and amberite cation exchange resin furnished two kinds of idarubicinone-7-beta-D-glucuronide (20 and 21) that are coupled at C-7 position of idarubicinone.

  DOI：

  10.1081/scc-120030758
• 作为产物：
  描述：

  2-Acetyl-1,2,3,4-tetrahydro-5,8-naphthoquinone 在 三氯化铝 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 4-demethoxy-7,9-dideoxydaunomycinone
  参考文献：
  名称：

  Mehendale, A. R.; Gupta, M.; Nagarajan, G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 205 - 207

  摘要：

  DOI：

文献信息

• A regioselective synthesis of 8,10-dideoxycarminomycinone
  作者：Allison E. Ashcroft、James K. Sutherland

  DOI：10.1039/c39810001075

  日期：——

  A carminomycinone derivative has been synthesised from 5-hydroxyquinizarin and 2-methoxy-5-methyl-4-nitromethyltetrahydrofuran.

  由5-羟基奎宁嗪和2-甲氧基-5-甲基-4-硝基甲基四氢呋喃合成了卡米霉素衍生物。
• Marschalk reaction approach for a simple synthesis of (±)4-demethoxydaunomycinone
  作者：A.B. Argade、A.R. Mehendale、N.R. Ayyangar

  DOI：10.1016/s0040-4039(00)84841-8

  日期：1986.1

  aldehyde 3 gave 2-(4′-oxo-n-pentane)-quinizarin 4b, which on formylation followed by second Marschalk reaction led to (±)-4-demethoxy-7,9-dideoxydaunomycinone 6 which is further exploited for the synthesis of (±)-4-demethoxydaunomycinone 1b.

  亮氨酸喹啉啉2与乙酰丙酸（氧代-缩酮）醛3的Marschalk反应产生了2-（4'-氧代-正戊烷）-喹嗪啉4b，在甲酰化之后进行第二次Marschalk反应导致（±）-4-脱甲氧基-7 ，9，9-二脱氧十二烷酮6被进一步用于合成（±）-4-demethoxydaunomycinone 1b。
• Synthesis of (+)-4-demethoxydaunomycinone
  申请人：THE TRUSTEES OF THE UNIVERSITY OF PENNSYLVANIA

  公开号：EP0129044A1

  公开（公告）日：1984-12-27

  It has been found that stereospecific R(-)-4-demethoxy , -7-deoxydaunomycinone can be synthesized from the known compound 4-demethoxy-7, 9-dideoxydaunomycinone. (R(-)-4-Demethoxy-7-deoxy-daunomycinone is an intermediate in the synthesis of (+)-4-demethoxydaunomycinone, the aglycone of the non-naturally occurring and antitumor active (-)7(S)9(S)-4-demethoxydaunorubicin.

  研究发现，立体特异性的 R(-)-4-去甲氧基、-7-脱氧大芸霉素酮可以从已知化合物 4-去甲氧基-7，9-脱氧大芸霉素酮合成。 R(-)-4-去甲氧基-7-脱氧大芸霉素酮是合成(+)-4-去甲氧基大芸霉素酮的中间体，而(+)-4-去甲氧基大芸霉素酮是非天然存在的具有抗肿瘤活性的(-)7(S)9(S)-4-去甲氧基大芸霉素的苷元。
• System and method for electrochemical detection of biological compounds
  申请人：Althaus S. John

  公开号：US20060207891A1

  公开（公告）日：2006-09-21

  The present invention relates to an electrochemical method for detecting a target polynucleotide. An electrode comprising an electrode surface is provided. The electrode surface includes at least one probe molecule reverisbly immobilized with respect to the electrode surface. A first electrochemical signal indicative of an amount of probe molecule immobilized with respect to the electrode surface is obtained. The electrode surface is contacted with a liquid comprising the target polynucleotide. Upon the contacting step, at least some of the probe molecule immobilized with respect to the electrode surface dissociates therefrom. A second electrochemical signal indicative of an amount of probe molecule immobilized with respect to the electrode surface is obtained. The presence of the target polynucleotide is determined at least partially on the basis of the first and second electrochemical signals.

  本发明涉及一种检测目标多核苷酸的电化学方法。提供了一种包括电极表面的电极。电极表面包括至少一个相对于电极表面可逆固定的探针分子。可获得指示相对于电极表面固定的探针分子量的第一电化学信号。电极表面与含有目标多核苷酸的液体接触。在接触步骤中，相对于电极表面固定的探针分子至少有一部分从电极表面解离。获得指示相对于电极表面固定的探针分子量的第二电化学信号。目标多核苷酸的存在至少部分是根据第一和第二电化学信号确定的。
• Gupta, Ramesh C.; Jackson, David A.; Stoodley, Richard J., Journal of the Chemical Society. Perkin transactions I, 1985, p. 525 - 534
  作者：Gupta, Ramesh C.、Jackson, David A.、Stoodley, Richard J.、Williams, David J.

  DOI：——

  日期：——