N-nonaflyl-(6-phenyl-hex-5-ynyl)-amine | 666705-69-7

• 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-nonaflyl-(6-phenyl-hex-5-ynyl)-amine
• 英文别名: N-nonaflyl-6-phenyl-5-hexynylamine；1,1,2,2,3,3,4,4,4-nonafluoro-N-(6-phenylhex-5-ynyl)butane-1-sulfonamide
• CAS: 666705-69-7
• 化学式: C₁₆H₁₄F₉NO₂S
• 分子量: 455.344
• InChiKey: JNNDHGRDHKVRFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-nonaflyl-(6-phenyl-hex-5-ynyl)-amine 在 四(三苯基膦)钯 、 三苯基膦 作用下， 以 苯 为溶剂， 反应 66.0h， 以86%的产率得到N-nonaflyl-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 lithium aluminium tetrahydride 、 sodium azide 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 N-nonaflyl-(6-phenyl-hex-5-ynyl)-amine
  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

• Catalytic Asymmetric Intramolecular Hydroamination of Alkynes in the Presence of a Catalyst System Consisting of Pd(0)-Methyl Norphos (or Tolyl Renorphos)-Benzoic Acid
  作者：Meda Narsireddy、Yoshinori Yamamoto

  DOI：10.1021/jo801785r

  日期：2008.12.19

  Renorphos (D), and tolyl Renorphos (E) were synthesized and used as chiral bisphosphine ligands for the catalyst system, Pd(2)(dba)(3) x CHCl(3)/PhCOOH, in an intramolecular hydroamination of aminoalkynes 15. Among the Norphos series, methyl Norphos (A) was the best ligand for the hydroamination, and the corresponding five- and six-membered nitrogen heterocycles 16 were obtained in high yields with high

  合成对映体纯的甲基Norphos（A），甲苯基Norphos（B），CF（3）Norphos（C），甲基Renorphos（D）和甲苯基Renorphos（E），并用作催化剂体系Pd（的手性双膦配体） 2）（dba）（3）x CHCl（3）/ PhCOOH，在氨基炔烃的分子内加氢胺化中。15.在Norphos系列中，甲基Norphos（A）是加氢胺化的最佳配体，相应的是5-和6-高收率和高对映选择性地获得了二元氮杂环16。在Renorphos系列中，甲苯基Renorphos（E）的结果最好。甲基Norphos（A）和甲苯基Renorphos（E）均具有高收率和高对映选择性。使用Me-Norphos进行的NMR研究表明，该配体在Pd（2）（dba）（3）存在下逐渐被氧化。即使在使用Ar气氛的条件下，C（6）D（6）中的CHCl（3）仍会生成Me-Norphos氧化物，从而阻止了分子内加氢胺化
• Palladium-Catalyzed Intramolecular Asymmetric Hydroamination, Hydroalkoxylation, and Hydrocarbonation of Alkynes
  作者：Nitin T. Patil、Léopold Mpaka Lutete、Huanyou Wu、Nirmal K. Pahadi、Ilya D. Gridnev、Yoshinori Yamamoto

  DOI：10.1021/jo0603835

  日期：2006.5.1

  A conceptually novel approach for asymmetric intramolecular hydroamination, hydroalkoxylation and hydrocarbonation of alkynes using chiral palladium catalysts are described. The reactions of the aminoalkynes 5, alkynols 7, and alkynylmethines 9 in the presence of Pd-2(dba)(3)center dot CHCl3/PhCOOH/renorphos 4 in benzene (or benzene-hexane) at 100 degrees C gave the corresponding cyclization products (nitrogen heterocycles 6, oxygen heterocycles 8, and carbocycles 10) in good yields with good enantioselectivities. The origins of enantioselectivities in the hydroamination reaction are discussed based on DFT computations.
• Palladium-Catalyzed Intramolecular Asymmetric Hydroamination of Alkynes
  作者：Léopold M. Lutete、Isao Kadota、Yoshinori Yamamoto

  DOI：10.1021/ja039774g

  日期：2004.2.1

  The Pd-catalyzed reaction of internal alkynes with tethered amino groups in the presence of PhCO2H and RENORPHOS as chiral phosphine ligand is reported. Various five- and six-membered nitrogen-containing heterocycles were obtained in good to high yield with moderate to high ee.
• 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.