(1S,2R)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-1,2-diol | 123072-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1S,2R)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-1,2-diol
• 英文别名: (1R,2R)-2-acetyl-1,2,3,4-tetrahydro-5,8-dimethoxynaphthalene-1,2-diol；1-[(1S,2R)-1,2-dihydroxy-5,8-dimethoxy-3,4-dihydro-1H-naphthalen-2-yl]ethanone
• CAS: 123072-12-8
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: HODWFSILEQVERX-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (1S,2R)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-1,2-diol 在 三甲基氯硅烷 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (1R,2S)-2-acetoxy-2-acetyl-1-chloro-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Efficient enantioselective synthesis of (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, the key intermediate in the synthesis of anthracycline antibiotics

  摘要：

  A simple, efficient, enantioselective synthesis of (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, the key intermediate in the synthesis of anthracycline antibiotics, is described. The synthetic procedure starts with the Sharpless asymmetric dihydroxylation of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: the diol obtained is regioselectively transformed into the corresponding chloroacetate which is dehalogenated and saponified to give the desired title compound in four steps with satisfactory yield (52%). No separation step is necessary at any point or the synthetic process. An efficient procedure for the synthesis of the starting enone and the stereoselectivity of the methanolysis of the intermediate chloroacetate are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00531-6
• 作为产物：
  描述：

  5,8-二甲氧基-1,2-二氢萘 在 AD-mix-α 、 三氯化铝 、 potassium dioxotetrahydroxoosmate(VI) 、 甲基磺酰胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 96.5h， 生成 (1S,2R)-2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-1,2-diol
  参考文献：
  名称：

  Efficient enantioselective synthesis of (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, the key intermediate in the synthesis of anthracycline antibiotics

  摘要：

  A simple, efficient, enantioselective synthesis of (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, the key intermediate in the synthesis of anthracycline antibiotics, is described. The synthetic procedure starts with the Sharpless asymmetric dihydroxylation of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: the diol obtained is regioselectively transformed into the corresponding chloroacetate which is dehalogenated and saponified to give the desired title compound in four steps with satisfactory yield (52%). No separation step is necessary at any point or the synthetic process. An efficient procedure for the synthesis of the starting enone and the stereoselectivity of the methanolysis of the intermediate chloroacetate are also reported. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00531-6

文献信息

• A short asymmetric synthesis of anthracycline antibiotics
  作者：Kiyoshi Tomioka、Makoto Nakajima、Kenji Koga

  DOI：10.1039/c39890001921

  日期：——

  Enantioselective dihydroxylation of (7) with osmium tetroxide with mediation by the chiral diamine (–)-(6) afforded (9) of 82% enantiomeric excess which was then successfully converted to (+)-4-demethoxydaunomycinone (5).

  在手性二胺（-）-（6）的介导下，用四氧化对（7）进行对映选择性二羟基化，得到（9）82％的对映体过量，然后将其成功转化为（+）-4-脱甲氧基十二烷酮（5）。
• Short-step asymmetric syntheses of anthracycline antibiotics via enantioselective dihydroxylation by osmium tetroxide with a chiral diamine
  作者：Makoto Nakajima、Kiyoshi Tomioka、Kenji Koga

  DOI：10.1016/s0040-4020(01)80235-0

  日期：1993.1

  Short-step asymmetric syntheses of (+)-7-dehydroxy-4-demethoxydaunornycinone 4 and (-)-9-deacetyl-1-7-dehydroxy-4-demethoxy-9-hydroxymethyldaunomycinone 5 were accomplished via enantioselective dihydroxylation by osmium tetroxide with chiral diamine 13.
• TOMIOKA, KIYOSHI;NAKAJIMA, MAKOTO;KOGA, KENJI, J. CHEM. SOC. CHEM. COMMUN.,(1989) N4, C. 1921-1922
  作者：TOMIOKA, KIYOSHI、NAKAJIMA, MAKOTO、KOGA, KENJI

  DOI：——

  日期：——