6,9,11-trihydroxy-9-(2-methyl-1,3-dioxolan-2-yl)-8,10-dihydro-7H-tetracene-5,12-dione | 86423-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 6,9,11-trihydroxy-9-(2-methyl-1,3-dioxolan-2-yl)-8,10-dihydro-7H-tetracene-5,12-dione
• CAS: 86423-66-7
• 化学式: C₂₂H₂₀O₇
• 分子量: 396.397
• InChiKey: ZUFGDACKBLBBMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6,9,11-trihydroxy-9-(2-methyl-1,3-dioxolan-2-yl)-8,10-dihydro-7H-tetracene-5,12-dione 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 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 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：

  1,2,3,4-tetrahydro-5,8-dimethoxy-4-oxonaphthalene-2-carboxylic acid 在 三乙基硅烷 、 三氯化铝 、 potassium tert-butylate 、 氧气 、 对甲苯磺酸 、 三氟乙酸 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 硝基苯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 3.5h， 生成 6,9,11-trihydroxy-9-(2-methyl-1,3-dioxolan-2-yl)-8,10-dihydro-7H-tetracene-5,12-dione
  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

文献信息

• MURAMATSU, MITIXISA;SATO, XIROMI;ISIGURO, KIKUO;KATIBU, DZYUNMOTO
  作者：MURAMATSU, MITIXISA、SATO, XIROMI、ISIGURO, KIKUO、KATIBU, DZYUNMOTO

  DOI：——

  日期：——
• ISIDZUMI, KIKUO;TANNO, KIXIKO;MURAMATSU, MITIXISA;JOSIDA, NOBORU;SATO, XI+
  作者：ISIDZUMI, KIKUO、TANNO, KIXIKO、MURAMATSU, MITIXISA、JOSIDA, NOBORU、SATO, XI+

  DOI：——

  日期：——
• ——
  作者：ISHIZUMI KIKUO、 MURAMATSU MICHIHISA、 TANNO NORIHIKO、 SATO HIROMI、 YOSHIDA+

  DOI：——

  日期：——
• Facile Total Syntheses of Idarubicinone‐7‐β‐<scp>D</scp>‐glucuronide: Convenient Preparations of AB‐Ring Synthon Using Some Carboxylic Acid Derivatives
  作者：Young S. Rho、Jihyung Park、Gyuil Kim、Hyesun Kim、Hongsig Sin、Pyoung Won Suh、Dong Jin Yoo

  DOI：10.1081/scc-120030758

  日期：2004.12.31

  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.