N-(trifluoroacetyl)-4-(aminomethyl)-1,7-diphenyl-1,6-heptadiyne | 1049012-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(trifluoroacetyl)-4-(aminomethyl)-1,7-diphenyl-1,6-heptadiyne
• CAS: 1049012-26-1
• 化学式: C₂₂H₁₈F₃NO
• 分子量: 369.386
• InChiKey: ALYZIUXWPGTRLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(trifluoroacetyl)-4-(aminomethyl)-1,7-diphenyl-1,6-heptadiyne 在 sodium hydroxide 、 乙醇 作用下， 反应 20.0h， 以95%的产率得到4-(aminomethyl)-1,7-diphenyl-1,6-heptadiyne
  参考文献：
  名称：

  Intramolecular Hydroamination of Aminoalkynes with Silver−Phenanthroline Catalysts

  摘要：

  Intramolecular hydroamination of several aminoalkynes catalyzed by silver-phenanthroline complexes is reported. This catalyst system complements previous protocols by employing air- and moisture-stable complexes without compromising activity or reaction control. Some of the hydroamination products are subject to a useful aerobic oxidation. Silver-phenanthroline complexes have successfully demonstrated efficacy in the desymmetrization of a prochiral diyne.

  DOI：

  10.1021/ol801458g
• 作为产物：
  描述：

  2,2,2-三氟乙酰胺 、 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.0h， 以0.050 g的产率得到N-(trifluoroacetyl)-4-(aminomethyl)-1,7-diphenyl-1,6-heptadiyne
  参考文献：
  名称：

  Intramolecular Hydroamination of Aminoalkynes with Silver−Phenanthroline Catalysts

  摘要：

  Intramolecular hydroamination of several aminoalkynes catalyzed by silver-phenanthroline complexes is reported. This catalyst system complements previous protocols by employing air- and moisture-stable complexes without compromising activity or reaction control. Some of the hydroamination products are subject to a useful aerobic oxidation. Silver-phenanthroline complexes have successfully demonstrated efficacy in the desymmetrization of a prochiral diyne.

  DOI：

  10.1021/ol801458g

文献信息

• Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I
  作者：Vijaya Bhaskara Reddy Iska、Vincenzo Verdolino、Olaf Wiest、Paul Helquist

  DOI：10.1021/jo902674j

  日期：2010.2.19

  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.