N-(3-(3,3-dimethylbut-1-ynyl)-3-hydroxy-6,6-dimethylhept-4-ynyl)-2,2,2-trifluoroacetamide | 1207670-11-8

• 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: N-(3-(3,3-dimethylbut-1-ynyl)-3-hydroxy-6,6-dimethylhept-4-ynyl)-2,2,2-trifluoroacetamide
• CAS: 1207670-11-8
• 化学式: C₁₇H₂₄F₃NO₂
• 分子量: 331.378
• InChiKey: RIWMZZIFXCZPRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 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：

  N-(3-(3,3-dimethylbut-1-ynyl)-3-hydroxy-6,6-dimethylhept-4-ynyl)-2,2,2-trifluoroacetamide 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到5-(2-aminoethyl)-2,2,8,8-tetramethylnona-3,6-diyn-5-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：

  3,3-二甲基-1-丁炔 、 methyl 3-(2,2,2-trifluoroacetamido)propanoate 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90%的产率得到N-(3-(3,3-dimethylbut-1-ynyl)-3-hydroxy-6,6-dimethylhept-4-ynyl)-2,2,2-trifluoroacetamide
  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