methyl (1R,2R,4S)-4-hydroxy-2-nitrocyclopentanecarboxylate | 1220627-44-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,2R,4S)-4-hydroxy-2-nitrocyclopentanecarboxylate
• CAS: 1220627-44-0
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: AXOPEMMWGGOBNZ-KVQBGUIXSA-N

物化性质

• 沸点：
  317.8±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

反应信息

• 作为反应物：
  描述：

  methyl (1R,2R,4S)-4-hydroxy-2-nitrocyclopentanecarboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以81%的产率得到methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate
  参考文献：
  名称：

  Studies on the stereocontrolled transformation of nitrohexofuranoses into 2-oxabicyclo[2.2.1]heptanes. V: Synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate

  摘要：

  The first total synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on an intramolecular cyclisation leading to 2-oxabicyclo[2 2 1]heptane derivatives It was observed that on of the substrate anomers produces an elimination rather than a cyclisation reaction These and other differences in the reaction paths for this key step were rationalised by means of molecular mechanism based Calculations. (c) 2010 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetasy.2009.12.018
• 作为产物：
  描述：

  、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 为溶剂， 反应 0.25h， 以0.38 g的产率得到methyl (1R,2R,4S)-4-hydroxy-2-nitrocyclopentanecarboxylate
  参考文献：
  名称：

  Studies on the stereocontrolled transformation of nitrohexofuranoses into 2-oxabicyclo[2.2.1]heptanes. V: Synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate

  摘要：

  The first total synthesis of enantiopure methyl (1R,2R,4S)-2-amino-4-hydroxycyclopentanecarboxylate was carried out according to our recent novel strategy for the transformation of nitrohexofuranoses into cyclopentylamines, which is based on an intramolecular cyclisation leading to 2-oxabicyclo[2 2 1]heptane derivatives It was observed that on of the substrate anomers produces an elimination rather than a cyclisation reaction These and other differences in the reaction paths for this key step were rationalised by means of molecular mechanism based Calculations. (c) 2010 Published by Elsevier Ltd

  DOI：

  10.1016/j.tetasy.2009.12.018