Acetic acid (1S,2R,3S,4R)-2,3,4,5-tetraacetoxy-1-((3aR,4S,7S,7aR,8S)-7-nitro-3a,4,7,7a-tetrahydro-3H-4,7-ethano-inden-8-yl)-pentyl ester | 205248-19-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (1S,2R,3S,4R)-2,3,4,5-tetraacetoxy-1-((3aR,4S,7S,7aR,8S)-7-nitro-3a,4,7,7a-tetrahydro-3H-4,7-ethano-inden-8-yl)-pentyl ester
• CAS: 205248-19-7
• 化学式: C₂₆H₃₃NO₁₂
• 分子量: 551.548
• InChiKey: AHRPOMHZIRMDJK-LURNAYLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  39.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  174.64
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,2R,3S,4R)-2,3,4,5-tetraacetoxy-1-((3aR,4S,7S,7aR,8S)-7-nitro-3a,4,7,7a-tetrahydro-3H-4,7-ethano-inden-8-yl)-pentyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.75h， 以73%的产率得到(1S,2R,3S,4R)-1-((3aR,4S,7S,7aR,8S)-7-Nitro-3a,4,7,7a-tetrahydro-3H-4,7-ethano-inden-8-yl)-pentane-1,2,3,4,5-pentaol
  参考文献：
  名称：

  Enantioselective synthesis of 1-nitrotricyclo[5,2,2,02,6]undeca-3,8-dienes via tandem consecutive asymmetric Diels–Alder reaction–Cope rearrangement

  摘要：

  The 1-glyco-2-nitrocyclohexa-2,4-dienes 1a and 5a react with cyclopentadiene to yield, almost exclusively, the 10-glyco-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes 4a and 8a. Formation of these products is explained as the result of a tandem consecutive asymmetric Diels-Alder reaction-Cope rearrangement. Periodate oxidation of deprotected sugar side-chains, followed by sodium borohydride reduction yielded enantiomerically pure 10-formyl- and 10-hydroxymethyl-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes. Structures have been determined by X-ray crystallographic and spectroscopic analyses, and chemical correlation. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00627-7
• 作为产物：
  描述：

  环戊二烯 、 1',2',3',4',5'-penta-O-acetyl-1'-C-[(1S)-2-nitrocyclohexa-2,4-dienyl]-D-galacto-pentitol 以 甲苯 为溶剂， 反应 96.0h， 以18 mg的产率得到Acetic acid (1S,2R,3S,4R)-2,3,4,5-tetraacetoxy-1-((1S,4R,4aR,6S,8aS)-7-nitro-1,4,4a,5,6,8a-hexahydro-1,4-methano-naphthalen-6-yl)-pentyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 1-nitrotricyclo[5,2,2,02,6]undeca-3,8-dienes via tandem consecutive asymmetric Diels–Alder reaction–Cope rearrangement

  摘要：

  The 1-glyco-2-nitrocyclohexa-2,4-dienes 1a and 5a react with cyclopentadiene to yield, almost exclusively, the 10-glyco-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes 4a and 8a. Formation of these products is explained as the result of a tandem consecutive asymmetric Diels-Alder reaction-Cope rearrangement. Periodate oxidation of deprotected sugar side-chains, followed by sodium borohydride reduction yielded enantiomerically pure 10-formyl- and 10-hydroxymethyl-1-nitrotricyclo[5,2,2,0(2,6)]undeca-3,8-dienes. Structures have been determined by X-ray crystallographic and spectroscopic analyses, and chemical correlation. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00627-7