(3R)-3-C-nitromethyl-1,2:5,6-di-O-cyclohexylidene-α-D-allofuranose | 66843-65-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R)-3-C-nitromethyl-1,2:5,6-di-O-cyclohexylidene-α-D-allofuranose
• 英文别名: (3aR,5R,6R,6aR)-5-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]-6-(nitromethyl)spiro[5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-ol
• CAS: 66843-65-0
• 化学式: C₁₉H₂₉NO₈
• 分子量: 399.441
• InChiKey: YMKQCSKTCYVRBC-RUEZSYAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R)-3-C-nitromethyl-1,2:5,6-di-O-cyclohexylidene-α-D-allofuranose 在 palladium 10% on activated carbon 、 氢气 、 苄基三甲基氯化铵 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 40.0 ℃ 、4.05 MPa 条件下， 反应 15.67h， 生成 (3R)-1,2:5,6-di-O-cyclohexylidene-spiro(3-deoxy-α-D-allofuranose-3,5'-oxazolidin)-2'-one
  参考文献：
  名称：

  Novel 3-C-aminomethyl-hexofuranose-derived thioureas and their testing in asymmetric catalysis

  摘要：

  Both 1,2:5,6-di-O-isopropylidene- and 1,2:5,6-di-O-cyclohexylidene-alpha-D-glucofuranose-derived ketones provided the corresponding branched 3-C-nitromethyl-congeners in the Henry reaction with nitromethane anion. Reduction of the nitro moiety followed by derivatization with iso(thio)cyanates gave 3-C-aminomethyl-hexofuranose-derived (thio)ureas. The relative configuration of the products in each series was unambiguously established by X-ray analysis. The title products were shown to act as organocatalysts in Friedel Crafts alkylations of indoles with beta-nitrostyrenes and in Michael additions of nitromethane to trans-chalcones. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.07.003
• 作为产物：
  描述：

  硝基甲烷 、 1,2:5,6-二-O-环己亚基-alpha-D-呋喃葡萄糖 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 水 、 sodium bromide 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 0.5h， 以61%的产率得到(3R)-3-C-nitromethyl-1,2:5,6-di-O-cyclohexylidene-α-D-allofuranose
  参考文献：
  名称：

  Novel 3-C-aminomethyl-hexofuranose-derived thioureas and their testing in asymmetric catalysis

  摘要：

  Both 1,2:5,6-di-O-isopropylidene- and 1,2:5,6-di-O-cyclohexylidene-alpha-D-glucofuranose-derived ketones provided the corresponding branched 3-C-nitromethyl-congeners in the Henry reaction with nitromethane anion. Reduction of the nitro moiety followed by derivatization with iso(thio)cyanates gave 3-C-aminomethyl-hexofuranose-derived (thio)ureas. The relative configuration of the products in each series was unambiguously established by X-ray analysis. The title products were shown to act as organocatalysts in Friedel Crafts alkylations of indoles with beta-nitrostyrenes and in Michael additions of nitromethane to trans-chalcones. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.07.003

文献信息

• Zhdanov, Yu. A.; Alekseev, Yu. E.; Doroshenko, S. S., Doklady Chemistry, 1982, vol. 262, p. 51 - 52
  作者：Zhdanov, Yu. A.、Alekseev, Yu. E.、Doroshenko, S. S.

  DOI：——

  日期：——