methyl 3-((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propiolate | 1373038-73-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propiolate
• 英文别名: methyl 3-[(4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-ynoate
• CAS: 1373038-73-3
• 化学式: C₁₀H₁₃N₃O₄
• 分子量: 239.231
• InChiKey: KSEJMNLISJDSQW-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propiolate 在 对甲苯磺酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 生成 (4S,5S)-methyl 4,5-dihydroxy-5,6-dihydro-4H-pyrrolo[1,2-c][1,2,3]triazole-3-carboxylate
  参考文献：
  名称：

  Intramolecular Huisgen [3+2] cycloaddition in water: synthesis of fused pyrrolidine–triazoles

  摘要：

  The intramolecular alkyne-azide Huisgen [3+2] cycloaddition reaction as a 'click-chemistry' reaction without a metal catalyst has been studied under aerobic conditions. The synthesis of various pyrrolidine-triazole hybrid compounds has also been achieved by using this intramolecular cycloaddition reaction in water with complete 1,5-regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.02.011
• 作为产物：
  描述：

  (4S,5S)-4-hydroxymethyl-2,2-dimethyl-5-tosyloxymethyl-1,3-dioxolane 在 sodium azide 、 potassium carbonate 、 sodium amide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二甲基亚砜 、 乙酸乙酯 、 丙酮 为溶剂， 反应 16.75h， 生成 methyl 3-((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propiolate
  参考文献：
  名称：

  Intramolecular Huisgen [3+2] cycloaddition in water: synthesis of fused pyrrolidine–triazoles

  摘要：

  The intramolecular alkyne-azide Huisgen [3+2] cycloaddition reaction as a 'click-chemistry' reaction without a metal catalyst has been studied under aerobic conditions. The synthesis of various pyrrolidine-triazole hybrid compounds has also been achieved by using this intramolecular cycloaddition reaction in water with complete 1,5-regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.02.011

文献信息

• Intramolecular Huisgen [3+2] cycloaddition in water: synthesis of fused pyrrolidine–triazoles
  作者：Indresh Kumar、Nisar A. Mir、Chandrashaker V. Rode、Basant P. Wakhloo

  DOI：10.1016/j.tetasy.2012.02.011

  日期：2012.2

  The intramolecular alkyne-azide Huisgen [3+2] cycloaddition reaction as a 'click-chemistry' reaction without a metal catalyst has been studied under aerobic conditions. The synthesis of various pyrrolidine-triazole hybrid compounds has also been achieved by using this intramolecular cycloaddition reaction in water with complete 1,5-regioselectivity. (C) 2012 Elsevier Ltd. All rights reserved.