(2S)-N-(5-hydroxypentyl)-5-oxooxolane-2-carboxamide | 192050-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S)-N-(5-hydroxypentyl)-5-oxooxolane-2-carboxamide
• CAS: 192050-90-1
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: LQFAXOYFJXUUCO-QMMMGPOBSA-N

物化性质

• 沸点：
  516.4±50.0 °C(Predicted)
• 密度：
  1.196±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-N-(5-hydroxypentyl)-5-oxooxolane-2-carboxamide 在 吡啶 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (S)-5-Oxo-tetrahydro-furan-2-carboxylic acid (5-azido-pentyl)-amide
  参考文献：
  名称：

  Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5, 5 and nylon 5,6

  摘要：

  L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of the ester group of 3 with aminoalcohols. The alcohol function of the resulting N-(hydroxyalkyl)amides (4 and 9) was converted into amine by tosylation, azide substitution and hydrogenolysis. The amino lactones 7 and 12 thus obtained were conveniently functionalized for the polycondensation, which led to the stereoregular, crystalline polyamides 8 and 13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00121-3
• 作为产物：
  描述：

  (S)-(+)-5-氧代-2-四氢呋喃羧酸 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 (2S)-N-(5-hydroxypentyl)-5-oxooxolane-2-carboxamide
  参考文献：
  名称：

  Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5, 5 and nylon 5,6

  摘要：

  L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of the ester group of 3 with aminoalcohols. The alcohol function of the resulting N-(hydroxyalkyl)amides (4 and 9) was converted into amine by tosylation, azide substitution and hydrogenolysis. The amino lactones 7 and 12 thus obtained were conveniently functionalized for the polycondensation, which led to the stereoregular, crystalline polyamides 8 and 13. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00121-3

文献信息

• Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5, 5 and nylon 5,6
  作者：Hernán A. Orgueira、Oscar Varela

  DOI：10.1016/s0957-4166(97)00121-3

  日期：1997.5

  L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of the ester group of 3 with aminoalcohols. The alcohol function of the resulting N-(hydroxyalkyl)amides (4 and 9) was converted into amine by tosylation, azide substitution and hydrogenolysis. The amino lactones 7 and 12 thus obtained were conveniently functionalized for the polycondensation, which led to the stereoregular, crystalline polyamides 8 and 13. (C) 1997 Elsevier Science Ltd.