(2S,3R)-4E-2-acetamido-7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorododec-4-ene-1,3-diol | 1392096-35-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-4E-2-acetamido-7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorododec-4-ene-1,3-diol
• CAS: 1392096-35-3
• 化学式: C₁₄H₁₄F₁₃NO₃
• 分子量: 491.249
• InChiKey: PWOHEXQPYHDGLF-RIAPOHOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-4E-2-acetamido-7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorododec-4-ene-1,3-diol 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以81%的产率得到(2S,3R)-2-acetamido-7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorododec-1,3-diol
  参考文献：
  名称：

  Sphingosine and clavaminol H derivatives bearing fluorinated chains and their cytotoxic activity

  摘要：

  Microwave induced cross-metathesis of perfluoroalkylated propenes with a substituted allyl alcohol is a simple and straightforward method for the synthesis of sphingosine derivatives possessing perfluoroalkyl chains. One of the prepared compounds was converted into the fluorinated clavaminol H derivative and its deacetylated congener. Selected compounds were subjected to preliminary testing for cytotoxic activity on several cancer cell lines. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.005
• 作为产物：
  描述：

  (2S,3R)-4E-2-acetamido-7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorododec-4-ene-1,3-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以87%的产率得到(2S,3R)-4E-2-acetamido-7,7,8,8,9,9,10,10,11,11,12,12,12-tridecafluorododec-4-ene-1,3-diol
  参考文献：
  名称：

  Sphingosine and clavaminol H derivatives bearing fluorinated chains and their cytotoxic activity

  摘要：

  Microwave induced cross-metathesis of perfluoroalkylated propenes with a substituted allyl alcohol is a simple and straightforward method for the synthesis of sphingosine derivatives possessing perfluoroalkyl chains. One of the prepared compounds was converted into the fluorinated clavaminol H derivative and its deacetylated congener. Selected compounds were subjected to preliminary testing for cytotoxic activity on several cancer cell lines. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.06.005