| 1408311-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• CAS: 1408311-55-6
• 化学式: C₁₁H₁₅N₃O₄
• 分子量: 253.258
• InChiKey: MRVBYQLOIUGZSI-LNFKQOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.58
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  78.63
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  异山梨醇 在 CuIP(OEt)3 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 sodium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  RAFT Polymerization of Bio-Based 1-Vinyl-4-dianhydrohexitol-1,2,3-triazole Stereoisomers Obtained via Click Chemistry

  摘要：

  Four 1-vinyl-4-dianhydrohexitol-1,2,3-triazole stereoisomers are prepared from isomannide, isoidide, and isosorbide using an alkylation/CuAAC-ligation/elimination three-step strategy. After characterization of the monomers by NMR, differential scanning calorimetry (DSC), and high-resolution mass spectrometry (HRMS), the corresponding stereocontrolled poly(1-vinyl-4-dianhydrohexitol-1,2,3-triazole)s are obtained by RAFT polymerization using a xanthate chain transfer agent. A systematic investigation of the structure-properties relationship of both the monomers and polymers highlights the significant impact of the dianhydrohexitols stereochemistry on their physical properties (H-1 and C-13 NMR chemical shifts, physical state, T-g, thermal stability and solubility). A particularly original and unexpected behavior is highlighted since the two different isosorbide-based poly(1-vinyl-4-dianhydrohexitol-1,2,3-triazole) stereoisomers exhibit contrasting solubility in water.

  DOI：

  10.1021/bm301435e

文献信息

• RAFT Polymerization of Bio-Based 1-Vinyl-4-dianhydrohexitol-1,2,3-triazole Stereoisomers Obtained via Click Chemistry
  作者：Samir Beghdadi、Imen Abdelhedi Miladi、Hatem Ben Romdhane、Julien Bernard、Eric Drockenmuller

  DOI：10.1021/bm301435e

  日期：2012.12.10

  Four 1-vinyl-4-dianhydrohexitol-1,2,3-triazole stereoisomers are prepared from isomannide, isoidide, and isosorbide using an alkylation/CuAAC-ligation/elimination three-step strategy. After characterization of the monomers by NMR, differential scanning calorimetry (DSC), and high-resolution mass spectrometry (HRMS), the corresponding stereocontrolled poly(1-vinyl-4-dianhydrohexitol-1,2,3-triazole)s are obtained by RAFT polymerization using a xanthate chain transfer agent. A systematic investigation of the structure-properties relationship of both the monomers and polymers highlights the significant impact of the dianhydrohexitols stereochemistry on their physical properties (H-1 and C-13 NMR chemical shifts, physical state, T-g, thermal stability and solubility). A particularly original and unexpected behavior is highlighted since the two different isosorbide-based poly(1-vinyl-4-dianhydrohexitol-1,2,3-triazole) stereoisomers exhibit contrasting solubility in water.