(S,S)-(2-Nitrocyclopropyl)methanol | 148123-99-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S,S)-(2-Nitrocyclopropyl)methanol
• 英文别名: (1S,2S)-(trans-2-Nitrocyclopropyl)methanol；[(1S,2S)-2-nitrocyclopropyl]methanol
• CAS: 148123-99-3
• 化学式: C₄H₇NO₃
• 分子量: 117.104
• InChiKey: NNWLZXCTNYEQIL-DMTCNVIQSA-N

物化性质

• 沸点：
  240.3±9.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,S)-(2-Nitrocyclopropyl)methanol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以91%的产率得到(1S,2S)-1-Bromo(trans-2-nitrocyclopropyl)methane
  参考文献：
  名称：

  Synthesis of 3-(trans-2′-nitrocyclopropyl)alanine: An unusual natural amino acid

  摘要：

  Racemic (trans-2'-nitrocyclopropyl)methanol rac-7 is prepared in three steps from t-butyl acrylate, while enantiopure (1'S,2'S)-7 and (1'R,2'R)-7 is obtained in six steps from (R)- and (S)-2,3-O-isopropylideneglyceraldehyde, respectively. The alcohol 7 can be transformed to the bromide 8 and this in turn coupled with the glycine equivalent 2-(diphenylmethylenamino)acetate 9 to yield 3-(trans-2'-nitrocyclopropyl)alanine (Ala(3-Ncp)) 11, after deprotection. The natural material, part of the peptide-lactone hormaomycin, has (1'R,2'R)-configuration, as determined by comparison with the synthesized authentic compounds.

  DOI：

  10.1016/s0040-4039(00)91962-2
• 作为产物：
  描述：

  (1S,2S)-<(Triphenylmethyl)oxy>-(trans-2-nitrocyclopropyl)methane 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以87%的产率得到(S,S)-(2-Nitrocyclopropyl)methanol
  参考文献：
  名称：

  Synthesis of 3-(trans-2'-Nitrocyclopropyl)alanine, a Constituent of the Natural Peptide-Lactone Hormaomycin

  摘要：

  The peptide-lactone hormaomycin 1a produced by Streptomyces griseoflavus contains two molecules of 3-(trans-2'-nitrocyclopropyl)alanine [Ala(3-Ncp)] (6). In order to determine the unknown absolute configurations of these unusual natural amino acid molecules, which supposedly are essential for the biological activity of 1a, enantiopure alcohols (trans-2-nitrocyclopropyl)methanol [(1S,2S)-13 and (1R,2R)-13] have been prepared in six steps from (R)- and (S)-2,3-O-isopropylideneglyceral-dehyde (17). The alcohols 13 were transformed to the bromides 23, and these in turn were coupled with suitable glycine equivalents like 2-[(diphenylmethylene)amino]acetates (24) to yield (2R/S,1'S,2'S)- and (2R/S,1'R,2'R)-3-(trans-2'-nitrocyclopropyl)alanines (6), after deprotection. The natural compound la contains one molecule each with (2R,1'R,2'R)- and (2S,1'R,2'R)-configuration, as established by comparison of the hydrolysate from natural la with the synthesized samples of (2R/S,1'R,2'R)-6 and (2R/S,1'S,2'S)-6.

  DOI：

  10.1021/jo00115a009

文献信息

• Brandl; Kozhushkov; Loscha, Synlett, 2000, # 12, p. 1741 - 1744
  作者：Brandl、Kozhushkov、Loscha、Kokoreva、Yufit、Howard、De Meijere

  DOI：——

  日期：——