(3R,4S,5S)-4,5-dimethoxy-6-(prop-2-enylamino)hex-1-en-3-ol | 1131041-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4S,5S)-4,5-dimethoxy-6-(prop-2-enylamino)hex-1-en-3-ol
• CAS: 1131041-39-8
• 化学式: C₁₁H₂₁NO₃
• 分子量: 215.293
• InChiKey: JXIRLHBVVOMDTL-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5S)-4,5-dimethoxy-6-(prop-2-enylamino)hex-1-en-3-ol 、 丁二酸单甲酯酰氯 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以14.8 g的产率得到(2S,3S,4R)N-allyl,N-(methylsuccinyl)-4-hydroxy-2,3-dimethoxyhex-5-eneamine
  参考文献：
  名称：

  A Hydrophilic Azacyclooctyne for Cu-Free Click Chemistry

  摘要：

  Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. Here, we report the synthesis and evaluation of a novel azacyclooctyne, 6,7-dimethoxyazacyclooct-4-yne (DIMAC). Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. However, its superior polarity and water solubility reduced nonspecific binding, thereby improving the sensitivity of azide detection.

  DOI：

  10.1021/ol801141k
• 作为产物：
  描述：

  methyl 6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 、 丙烯胺 在 sodium cyanoborohydride 、 锌 作用下， 以 丙醇 、 水 为溶剂， 反应 1.0h， 生成 (3R,4S,5S)-4,5-dimethoxy-6-(prop-2-enylamino)hex-1-en-3-ol
  参考文献：
  名称：

  A Hydrophilic Azacyclooctyne for Cu-Free Click Chemistry

  摘要：

  Biomolecules labeled with azides can be detected through Cu-free click chemistry with cyclooctyne probes, but their intrinsic hydrophobicity can compromise bioavailability. Here, we report the synthesis and evaluation of a novel azacyclooctyne, 6,7-dimethoxyazacyclooct-4-yne (DIMAC). Generated in nine steps from a glucose analogue, DIMAC reacted with azide-labeled proteins and cells similarly to cyclooctynes. However, its superior polarity and water solubility reduced nonspecific binding, thereby improving the sensitivity of azide detection.

  DOI：

  10.1021/ol801141k