N-[(3S)-4,4,5,5,6,6,7,7,7-nonafluoro-1-phenylheptan-3-yl]acetamide | 1220105-02-1

• 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-[(3S)-4,4,5,5,6,6,7,7,7-nonafluoro-1-phenylheptan-3-yl]acetamide
• CAS: 1220105-02-1
• 化学式: C₁₅H₁₄F₉NO
• 分子量: 395.268
• InChiKey: FZXXMHDTLAOIRG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  N-[(Z)-4,4,5,5,6,6,7,7,7-nonafluoro-1-phenylhept-2-en-3-yl]acetamide 在 bis(norbornadiene)rhodium(l)tetrafluoroborate 、 双(二苯基膦)丁烷 、 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、3.55 MPa 条件下， 反应 20.0h， 以94%的产率得到N-[(3S)-4,4,5,5,6,6,7,7,7-nonafluoro-1-phenylheptan-3-yl]acetamide
  参考文献：
  名称：

  Highly enantioselective synthesis of α-(perfluoroalkyl)amines via hydrogenation of enamide precursors in the presence of chiraphos-rhodium catalyst

  摘要：

  Highly (up to 99% ee) enantio-enriched perfluoroalkyl amines can be synthesized by the perfluoroalkylation of nitriles with Lewis acidic perfluoroalkyl titanate reagents and catalytic asymmetric hydrogenation with the chiraphos-Rh catalyst of the resultant perfluoroalkyl enamides via base-mediated tautomerization. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.021

文献信息

• Sequential perfluoroalkylation and asymmetric reduction of nitriles triggered with perfluoroalkyl titanates: catalytic asymmetric synthesis of perfluoroalkyl amines
  作者：Koichi Mikami、Tatsushi Murase、Lili Zhai、Susumu Kawauchi、Yoshimitsu Itoh、Shigekazu Ito

  DOI：10.1016/j.tetlet.2009.12.140

  日期：2010.3

  Highly enantio-enriched perfluoroalkyl amines are shown to be synthesized by perfluoroalkylation and asymmetric reduction of nitriles. Perfluoroalkylation of nitriles can be attained by the Lewis acidic perfluoroalkyl titanate reagents to give acyclic ketimines. Catalytic asymmetric hydrogenation of the acyclic ketimines affords the perfluoroalkyl amine products in up to 93% ee.

  已显示通过全氟烷基化和腈的不对称还原来合成高度对映体富集的全氟烷基胺。可通过路易斯酸性全氟烷基钛酸酯试剂实现腈的全氟烷基化，得到无环酮亚胺。无环酮亚胺的催化不对称氢化提供了高达93％ee的全氟烷基胺产物。
• Highly enantioselective synthesis of α-(perfluoroalkyl)amines via hydrogenation of enamide precursors in the presence of chiraphos-rhodium catalyst
  作者：Koichi Mikami、Tatsushi Murase、Lili Zhai、Yoshimitsu Itoh、Shigekazu Ito

  DOI：10.1016/j.tetasy.2010.05.021

  日期：2010.5

  Highly (up to 99% ee) enantio-enriched perfluoroalkyl amines can be synthesized by the perfluoroalkylation of nitriles with Lewis acidic perfluoroalkyl titanate reagents and catalytic asymmetric hydrogenation with the chiraphos-Rh catalyst of the resultant perfluoroalkyl enamides via base-mediated tautomerization. (C) 2010 Elsevier Ltd. All rights reserved.