(-)-(7R,8R,9S)-7,8,9,10-tetrahydro-6,7,8,9,11-pentahydroxy-8,9-O-isopropylidene-9-methyl-11-methoxy-5,12-naphthacenequinone | 130353-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: (-)-(7R,8R,9S)-7,8,9,10-tetrahydro-6,7,8,9,11-pentahydroxy-8,9-O-isopropylidene-9-methyl-11-methoxy-5,12-naphthacenequinone
• 英文别名: (4R,5R,9S)-2,4-dihydroxy-12-methoxy-7,7,9-trimethyl-6,8-dioxapentacyclo[11.8.0.03,11.05,9.015,20]henicosa-1,3(11),12,15,17,19-hexaene-14,21-dione
• CAS: 130353-24-1
• 化学式: C₂₃H₂₂O₇
• 分子量: 410.423
• InChiKey: FEFFKMCOVHGVJX-LSWJPFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-(7R,8R,9S)-7,8,9,10-tetrahydro-6,7,8,9,11-pentahydroxy-8,9-O-isopropylidene-9-methyl-11-methoxy-5,12-naphthacenequinone 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到(+)-(8R)-9-deacetyl-8-hydroxy-9-methyl-4-demethoxydaunomycinone
  参考文献：
  名称：

  Anthracyclinones. 5. Glucosaccharino-1,4-lactone as a chiral template for the synthesis of new anthracyclinones

  摘要：

  Alkylation of dimethoxybenzene 16 with the chiral aldehyde derivative 14 prepared in six steps from alpha-D-glucosaccharino,1,4-lactone 3 afforded the adduct 17. After suitable transformation of 17, A ring closure was stereoselectively performed using SnCl4 at -70-degrees-C, giving 20. The tetralin-type quinone monoketal 23 obtained from 20 was then condensed with 27, and complete deprotection of anthracyclinones 28 and 29 led to 9-deacetyl-8(R)-hydroxy-9-methyl-4-demethoxydaunomycinone (6). On the other hand, 39, easily obtained from 14, was condensed with leucoquinizarin 31 to give after oxidation, intramolecular Marschalk reaction and benzylic deoxygenation, the corresponding 7-deoxyaglycon 7.

  DOI：

  10.1021/jo00001a073
• 作为产物：
  描述：

  (7R,8R,9S)-7-<(tert-butyldimethylsilyl)oxy>-7,8,9,10-tetrahydro-6,7,8,9-tetrahydroxy-8,9-O-isopropylidene-11-methoxy-9-methyl-5,12-naphthalenequinone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (-)-(7R,8R,9S)-7,8,9,10-tetrahydro-6,7,8,9,11-pentahydroxy-8,9-O-isopropylidene-9-methyl-11-methoxy-5,12-naphthacenequinone
  参考文献：
  名称：

  Anthracyclinones. 5. Glucosaccharino-1,4-lactone as a chiral template for the synthesis of new anthracyclinones

  摘要：

  Alkylation of dimethoxybenzene 16 with the chiral aldehyde derivative 14 prepared in six steps from alpha-D-glucosaccharino,1,4-lactone 3 afforded the adduct 17. After suitable transformation of 17, A ring closure was stereoselectively performed using SnCl4 at -70-degrees-C, giving 20. The tetralin-type quinone monoketal 23 obtained from 20 was then condensed with 27, and complete deprotection of anthracyclinones 28 and 29 led to 9-deacetyl-8(R)-hydroxy-9-methyl-4-demethoxydaunomycinone (6). On the other hand, 39, easily obtained from 14, was condensed with leucoquinizarin 31 to give after oxidation, intramolecular Marschalk reaction and benzylic deoxygenation, the corresponding 7-deoxyaglycon 7.

  DOI：

  10.1021/jo00001a073

文献信息

• DEGUIN, BRIGITTE;FLORENT, JEAN-CLAUDE;MONNERET, CLAUDE, J. ORG. CHEM., 56,(1991) N, C. 405-411
  作者：DEGUIN, BRIGITTE、FLORENT, JEAN-CLAUDE、MONNERET, CLAUDE

  DOI：——

  日期：——