(+)-(8S,9R)-7,8,9,10-tetrahydro-6,8,9,11-tetrahydroxy-8-methyl-5,12-naphthalenequinone | 130353-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: (+)-(8S,9R)-7,8,9,10-tetrahydro-6,8,9,11-tetrahydroxy-8-methyl-5,12-naphthalenequinone
• 英文别名: (8S,9R)-7,8,9,10-tetrahydro-6,8,9,11-tetrahydroxy-8,9-O-isopropylidenen-9-methyl-5,12-naphthacene quinone；(5S,9R)-2,12-dihydroxy-5,7,7-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: 130353-30-9
• 化学式: C₂₂H₂₀O₆
• 分子量: 380.397
• InChiKey: PGUHZDFJPQDEEX-PEBXRYMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-(8S,9R)-7,8,9,10-tetrahydro-6,8,9,11-tetrahydroxy-8-methyl-5,12-naphthalenequinone 在 水 、 溶剂黄146 作用下， 反应 3.0h， 生成 (-)-(8S,9R)-7,8,9,10-tetrahydro-6,8,9,11-tetrahydroxy-8-methyl-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
• 作为产物：
  描述：

  (2R,3R)-4-(1,4-dihydroxy-9,10-anthraquinono-2-yl)-2,3-dihydroxy-2,3-O-isopropylidene-2-methylbutanal 在 氢氧化钾 、 sodium dithionite 作用下， 生成 (+)-(8S,9R)-7,8,9,10-tetrahydro-6,8,9,11-tetrahydroxy-8-methyl-5,12-naphthalenequinone
  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

• Anthracyclinones. Part VIII. Synthesis of a 9-methyl anthracyclinone from d-glucose
  作者：Brigitte Deguin、Emmanuel Bertounesque、Gilbert Gaudel、Jean-Claude Florent、Claude Monneret

  DOI：10.1016/s0040-4020(01)81581-7

  日期：1992.6

  The chiral pool synthesis of enantiomerically pure anthracyclinone 6 from leucoquinizarin 10, and from 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribo-pentodialdo-1,4-furanose (9) readily obtained from diacetone glucose, is reported.

  对映体纯的蒽环酮6的手性池合成，由亮氨酸喹啉啉10和3- O-苄基-1,2 - O-异亚丙基-3-C-甲基-α- D-核糖戊二醛-1,4-呋喃糖合成（9据报道，从双丙酮葡萄糖中容易获得）。
• 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：——