(2R,5S,12R)-5-(dimethoxymethyl)-1,2,3,4,5,12-hexahydro-2-hydroxy-5,12-epoxynaphthacen-2-yl methyl ketone | 147863-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (2R,5S,12R)-5-(dimethoxymethyl)-1,2,3,4,5,12-hexahydro-2-hydroxy-5,12-epoxynaphthacen-2-yl methyl ketone
• CAS: 147863-60-3
• 化学式: C₂₃H₂₄O₅
• 分子量: 380.441
• InChiKey: YXKQGGAOZAZGHI-YMPZKCBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-methoxyphenyl)acrylic anhydride 、 (2R,5S,12R)-5-(dimethoxymethyl)-1,2,3,4,5,12-hexahydro-2-hydroxy-5,12-epoxynaphthacen-2-yl methyl ketone 在 4-二甲氨基吡啶 作用下， 以 乙醚 为溶剂， 反应 50.0h， 以31%的产率得到(2R,5S,12R)-2-acetyl-5-(dimethoxymethyl)-2-hydroxy-1,2,3,4,5,12-hexahydro-5,12-epoxynaphthacen-2-yl 3-(4'-methoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Asymmetric Synthesis and DNA Intercalation of (−)-6-[[(Aminoalkyl)oxy]methyl]-4-demethoxy-6,7- dideoxydaunomycinones^1,

  摘要：

  The BP3 . Et(2)O-promoted Diels-Alder addition of 1-acetylvinyl RADO(Et)-ate (RADO(Et)-ate = 3-ethyl-2-oxo-6,8-dioxa-3-azabicylo[3.2.1]octane-7-exo-carboxylate) to 1-(dimethosymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane led to one major monoadduct that added to 1,2-didehydrobenzene and was converted into (-)-4-demethoxy-7-deoxydaunomycinone and (2R)-12-acetoxy-2-acetyl-5-(bromomethyl)-1,2,3,4-tetrahydronaphthacen-2-yl RADO(Et)-ate. The latter compound was used to construct (8R)-8-acetyl-6,8-dihydroxy-11-[[(3'-[(aminopropyl)oxy]-, -4'-[(aminobutyl)oxy], and -5'-[(aminopenty)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione hydrochloride (-)-8, (-)-9, (-)-10, respectively, as well as (8R)-8-acetyl-6,8-dihydroxy-11-[[[2'-[(3 ''-aminopropyl)amino]ethyl]oxy]-((-)-11) and -[[[3'-[(3 ''-aminopropyl)amino]propyl]oxy]methyl]7,8,9,10--tetrahydronaphthacene-5,12-dione hydrochloride ((-)-12). (8R)-8-Acetyl-6,8-dihydroxy-11-[[(alpha-L-diaunosaminyl)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione hydrachloride ((-)-13), a mimic of idarubicin, was also prepared. Absorbance and fluorescence titration experiments showed (-)-8, (-)-9, and (-)-10 to intercalate calf thymus DNA whereas (-)-11, (-)-12, and (-)-13 did not. The best intercalator was (-)-9 (K-b = (1.1 +/- 0.1) x 10(5) M(-1)) with the [(4'-aminobutyl)oxy]-methyl chain. Inhibition of topoisomerase II-induced DNA strand religation wats observed for (-)-8 at a concentration of 50 mu M.

  DOI：

  10.1021/jo960606z
• 作为产物：
  描述：

  1-(dimethoxymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo<2.2.1>heptane 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 (2R,5S,12R)-5-(dimethoxymethyl)-1,2,3,4,5,12-hexahydro-2-hydroxy-5,12-epoxynaphthacen-2-yl methyl ketone
  参考文献：
  名称：

  Asymmetric Synthesis and DNA Intercalation of (−)-6-[[(Aminoalkyl)oxy]methyl]-4-demethoxy-6,7- dideoxydaunomycinones^1,

  摘要：

  The BP3 . Et(2)O-promoted Diels-Alder addition of 1-acetylvinyl RADO(Et)-ate (RADO(Et)-ate = 3-ethyl-2-oxo-6,8-dioxa-3-azabicylo[3.2.1]octane-7-exo-carboxylate) to 1-(dimethosymethyl)-2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane led to one major monoadduct that added to 1,2-didehydrobenzene and was converted into (-)-4-demethoxy-7-deoxydaunomycinone and (2R)-12-acetoxy-2-acetyl-5-(bromomethyl)-1,2,3,4-tetrahydronaphthacen-2-yl RADO(Et)-ate. The latter compound was used to construct (8R)-8-acetyl-6,8-dihydroxy-11-[[(3'-[(aminopropyl)oxy]-, -4'-[(aminobutyl)oxy], and -5'-[(aminopenty)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione hydrochloride (-)-8, (-)-9, (-)-10, respectively, as well as (8R)-8-acetyl-6,8-dihydroxy-11-[[[2'-[(3 ''-aminopropyl)amino]ethyl]oxy]-((-)-11) and -[[[3'-[(3 ''-aminopropyl)amino]propyl]oxy]methyl]7,8,9,10--tetrahydronaphthacene-5,12-dione hydrochloride ((-)-12). (8R)-8-Acetyl-6,8-dihydroxy-11-[[(alpha-L-diaunosaminyl)oxy]methyl]-7,8,9,10-tetrahydronaphthacene-5,12-dione hydrachloride ((-)-13), a mimic of idarubicin, was also prepared. Absorbance and fluorescence titration experiments showed (-)-8, (-)-9, and (-)-10 to intercalate calf thymus DNA whereas (-)-11, (-)-12, and (-)-13 did not. The best intercalator was (-)-9 (K-b = (1.1 +/- 0.1) x 10(5) M(-1)) with the [(4'-aminobutyl)oxy]-methyl chain. Inhibition of topoisomerase II-induced DNA strand religation wats observed for (-)-8 at a concentration of 50 mu M.

  DOI：

  10.1021/jo960606z