2-[(3aR,5S,6S,6aR)-5-formylspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-yl]oxyacetic acid | 1373392-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(3aR,5S,6S,6aR)-5-formylspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-yl]oxyacetic acid
• CAS: 1373392-11-0
• 化学式: C₁₃H₁₈O₇
• 分子量: 286.282
• InChiKey: LLECPMQCHXTEFU-SASUGWTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1,3,3-四甲基丁基异腈 、 2-[(3aR,5S,6S,6aR)-5-formylspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-yl]oxyacetic acid 、 邻氯苯胺 以 甲醇 为溶剂， 反应 13.0h， 以70%的产率得到(1S,2R,6R,8R,9R)-10-(2-chlorophenyl)-11-oxo-N-(2,4,4-trimethylpentan-2-yl)spiro[3,5,7,13-tetraoxa-10-azatricyclo[6.5.0.02,6]tridecane-4,1'-cyclohexane]-9-carboxamide
  参考文献：
  名称：

  A novel sugar based intramolecular Ugi 3CC for the N-alkyl-3-oxo-4-aryl-octahydrofuro[2,3-f][1,4]oxazepine-5-carboxamides

  摘要：

  An intramolecular Ugi reaction of 3-carboxy tethered sugar aldehyde with aryl amines and isocyanides has been accomplished to produce a novel class of carbohydrate derivatives, 3-oxo-4-aryl-octahydrofuro[2,3-f][1,4]oxazepine-5-carboxamides in good yields. The stereochemistry of the products was assigned by NMR studies. This is the first report on intramolecular Ugi reaction of 3-carboxy tethered sugar aldehyde, aryl amine, and isonitrile. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.02.048

文献信息

• A novel sugar based intramolecular Ugi 3CC for the N-alkyl-3-oxo-4-aryl-octahydrofuro[2,3-f][1,4]oxazepine-5-carboxamides
  作者：B.V. Subba Reddy、Nilanjan Majumder、T. Prabhakar Rao、B. Sridhar

  DOI：10.1016/j.tetlet.2012.02.048

  日期：2012.5

  An intramolecular Ugi reaction of 3-carboxy tethered sugar aldehyde with aryl amines and isocyanides has been accomplished to produce a novel class of carbohydrate derivatives, 3-oxo-4-aryl-octahydrofuro[2,3-f][1,4]oxazepine-5-carboxamides in good yields. The stereochemistry of the products was assigned by NMR studies. This is the first report on intramolecular Ugi reaction of 3-carboxy tethered sugar aldehyde, aryl amine, and isonitrile. (C) 2012 Elsevier Ltd. All rights reserved.