4-Nitro-benzoic acid (R)-2-acetyl-5-formyl-8-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl ester | 200440-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Nitro-benzoic acid (R)-2-acetyl-5-formyl-8-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl ester
• 英文别名: [(2R)-2-acetyl-5-formyl-8-hydroxy-3,4-dihydro-1H-naphthalen-2-yl] 4-nitrobenzoate
• CAS: 200440-98-8
• 化学式: C₂₀H₁₇NO₇
• 分子量: 383.357
• InChiKey: MPRQHFFQYGPQIG-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-Nitro-benzoic acid (R)-2-acetyl-5-formyl-8-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl ester 在 甲醇 、 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 抗癌药中间体
  参考文献：
  名称：

  Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

  摘要：

  The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1 derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the presence of an excess of t-BuMe2SiOSO2CF3 to yield an 83:17 mixture of two diastereomeric products which was converted into (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00433-3
• 作为产物：
  描述：

  3-(p-nitrobenzoyloxy)-3-buten-2-one 、 (1S,4R,4'S,5'S)-1-(4',5'-dimethyldioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene 在 叔丁基二甲硅基三氟甲磺酸酯 、 碳酸氢钠 作用下， 生成 4-Nitro-benzoic acid (R)-2-acetyl-5-formyl-8-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl ester 、 4-Nitro-benzoic acid (S)-2-acetyl-5-formyl-8-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-yl ester
  参考文献：
  名称：

  Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

  摘要：

  The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1 derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the presence of an excess of t-BuMe2SiOSO2CF3 to yield an 83:17 mixture of two diastereomeric products which was converted into (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00433-3

文献信息

• Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural
  作者：Viviane Theurillat-Moritz、Antonio Guidi、Pierre Vogel

  DOI：10.1016/s0957-4166(97)00433-3

  日期：1997.10

  The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan-2'-yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1 derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the presence of an excess of t-BuMe2SiOSO2CF3 to yield an 83:17 mixture of two diastereomeric products which was converted into (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone. (C) 1997 Elsevier Science Ltd.