N-benzyl-6-phenyl-5-hexynylamine | 146407-24-1

• 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-benzyl-6-phenyl-5-hexynylamine
• 英文别名: N-benzyl-6-phenylhex-5-yn-1-amine
• CAS: 146407-24-1
• 化学式: C₁₉H₂₁N
• 分子量: 263.382
• InChiKey: YXVQLBYMLRJJDM-UHFFFAOYSA-N

物化性质

• 沸点：
  407.6±28.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-6-phenyl-5-hexynylamine 在 四(三苯基膦)钯 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 72.0h， 以61%的产率得到N-benzyl-2-[(E)-2-phenylethenyl]pyrrolidine
  参考文献：
  名称：

  Intramolecular Hydroamination of Alkynes Catalyzed by Pd(PPh₃)₄/Triphenylphosphine under Neutral Conditions

  摘要：

  The intramolecular hydroamination of alkynes tethered with amino group 1 in the presence of catalytic amounts of Pd(PPh3)(4) and PPh3 in benzene at 100 degrees C proceeded smoothly without the use of any additional acid source to afford five and six-membered nitrogen heterocycles 2 in good to excellent yields. A compulsory addition of carboxylic acid as a cocatalyst was not needed, and the reaction could be carried out under essentially neutral conditions.

  DOI：

  10.1021/jo050412w
• 作为产物：
  描述：

  6-苯基己-5-炔-1-醇 在 氢氧化钾 、 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 N-benzyl-6-phenyl-5-hexynylamine
  参考文献：
  名称：

  Intramolecular Hydroamination of Alkynes Catalyzed by Pd(PPh₃)₄/Triphenylphosphine under Neutral Conditions

  摘要：

  The intramolecular hydroamination of alkynes tethered with amino group 1 in the presence of catalytic amounts of Pd(PPh3)(4) and PPh3 in benzene at 100 degrees C proceeded smoothly without the use of any additional acid source to afford five and six-membered nitrogen heterocycles 2 in good to excellent yields. A compulsory addition of carboxylic acid as a cocatalyst was not needed, and the reaction could be carried out under essentially neutral conditions.

  DOI：

  10.1021/jo050412w

文献信息

• Synthesis of Eight‐Membered Nitrogen Heterocycles via a Heterogeneous PtI ₂ ‐Catalyzed Cascade Cycloaddition Reaction of δ‐Aminoalkynes with Electron‐Deficient Alkynes
  作者：Xinhong Li、Songmeng Wang、Hongkai Wang、Weilin Wang、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1002/adsc.201901644

  日期：2020.4.8

  cascade reaction of δ‐aminoalkynes was developed for the synthesis of various eight‐membered nitrogen heterocycles in excellent yields. The reaction proceeds via a hydration of δ‐aminoalkynes and subsequent intramolecular cyclization and intermolecular addition as well as ring‐expansion cascade reaction with another electron‐deficient alkynes. This method has the advantages of simple operation and mild

  开发了新颖的δ-氨基炔烃的异质PtI 2催化级联反应，用于以优异的产率合成各种八元氮杂环。该反应通过δ-氨基炔烃的水合，随后的分子内环化和分子间加成以及与另一种缺电子炔烃的扩环级联反应而进行。该方法操作简单，反应条件温和。而且，没有任何支持物的简单PtI 2可以通过简单的离心而容易地回收，而不会在1,2-二氯乙烷（DCE）中大量丧失活性。PtI 2的可回收性可归因于其在DCE中的不溶性。反应构成正式 [6 + 2]-环加法。
• Palladium/Benzoic Acid Catalyzed Hydroamination of Alkynes
  作者：Isao Kadota、Akinori Shibuya、Leopold Mpaka Lutete、Yoshinori Yamamoto

  DOI：10.1021/jo990498r

  日期：1999.6.1
• Lutete, Leopold Mpaka; Kadota, Isao; Shibuya, Akinori, Heterocycles, 2002, vol. 58, p. 347 - 357
  作者：Lutete, Leopold Mpaka、Kadota, Isao、Shibuya, Akinori、Yamamoto, Yoshinori

  DOI：——

  日期：——
• Intramolecular Hydroamination of Alkynes Catalyzed by Pd(PPh₃)₄/Triphenylphosphine under Neutral Conditions
  作者：Gan B. Bajracharya、Zhibao Huo、Yoshinori Yamamoto

  DOI：10.1021/jo050412w

  日期：2005.6.1

  The intramolecular hydroamination of alkynes tethered with amino group 1 in the presence of catalytic amounts of Pd(PPh3)(4) and PPh3 in benzene at 100 degrees C proceeded smoothly without the use of any additional acid source to afford five and six-membered nitrogen heterocycles 2 in good to excellent yields. A compulsory addition of carboxylic acid as a cocatalyst was not needed, and the reaction could be carried out under essentially neutral conditions.