2,2,2-trifluoro-N-(3-(hex-1-ynyl)-3-hydroxynon-4-ynyl)acetamide | 1207670-96-9

• 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: 2,2,2-trifluoro-N-(3-(hex-1-ynyl)-3-hydroxynon-4-ynyl)acetamide
• CAS: 1207670-96-9
• 化学式: C₁₇H₂₄F₃NO₂
• 分子量: 331.378
• InChiKey: NCAOSZMLMVUDOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-N-(3-(hex-1-ynyl)-3-hydroxynon-4-ynyl)acetamide 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到7-(2-aminoethyl)trideca-5,8-diyn-7-ol
  参考文献：
  名称：

  Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I

  摘要：

  An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized I-pyrroline derivatives were synthesized in 73% to 88% isolated yields (>98% by H-1 NMR in some cases). The usefulness of this mild hydroamination method was further shown by the desymmetrization of unprotected tert-hydroxy diynes. Structures of two transition states have been studied computationally. An application of this method was demonstrated by a short and efficient synthesis of (+/-)-monomorine I.

  DOI：

  10.1021/jo902674j
• 作为产物：
  描述：

  methyl 3-(2,2,2-trifluoroacetamido)propanoate 、 1-己炔 在 正丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 以93%的产率得到2,2,2-trifluoro-N-(3-(hex-1-ynyl)-3-hydroxynon-4-ynyl)acetamide
  参考文献：
  名称：

  Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I

  摘要：

  An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized I-pyrroline derivatives were synthesized in 73% to 88% isolated yields (>98% by H-1 NMR in some cases). The usefulness of this mild hydroamination method was further shown by the desymmetrization of unprotected tert-hydroxy diynes. Structures of two transition states have been studied computationally. An application of this method was demonstrated by a short and efficient synthesis of (+/-)-monomorine I.

  DOI：

  10.1021/jo902674j