(1R,2S)-2-acetoxy-2-acetyl-1-chloro-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene | 428506-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (1R,2S)-2-acetoxy-2-acetyl-1-chloro-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene
• 英文别名: [(1R,2S)-2-acetyl-1-chloro-5,8-dimethoxy-3,4-dihydro-1H-naphthalen-2-yl] acetate
• CAS: 428506-52-9
• 化学式: C₁₆H₁₉ClO₅
• 分子量: 326.777
• InChiKey: VPHKQNWWROUONT-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-acetoxy-2-acetyl-1-chloro-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 在 sodium hydroxide 、 sodium methylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 77.0h， 生成 (1R,2R)-2-acetyl-2-hydroxy-1,5,8-trimethoxy-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：

  1-((3aR,9bS)-2,6,9-Trimethoxy-2-methyl-5,9b-dihydro-4H-naphtho[1,2-d][1,3]dioxol-3a-yl)-ethanone 在 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以9.41 g的产率得到(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

文献信息

• 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
  作者：Fabrizio Badalassi、Paolo Crotti、Cristina Di Bugno、Fabio D'Arata、Lucilla Favero、Alessio Ramacciotti

  DOI：10.1016/s0957-4166(01)00531-6

  日期：2001.12

  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.