4-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid | 709640-11-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid
• 英文别名: 4-Hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid
• CAS: 709640-11-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: VPRXNMJDNWWELR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid 在 甲基锂 作用下， 以95%的产率得到3,6-dimethoxy-11-oxatricyclo[7.2.1.0^2,7]dodeca-2,4,6-trien-10-one
  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 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到4-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid
  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

• 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.