4-(fluoro)-leu-enkephalin | 1227828-11-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(fluoro)-leu-enkephalin
• 英文别名: Boc-Phe(4-F)-Gly-Gly-Phe-Leu-OMe；methyl (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-3-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoate
• CAS: 1227828-11-6
• 化学式: C₃₄H₄₆FN₅O₈
• 分子量: 671.766
• InChiKey: QISUBZLYJMESTP-QKDODKLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  48
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  181
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-Boc-4-(tributylstannyl)-L-phenylalanyl-glycylglycyl-L-phenylalanyl-L-leucine methyl ester 在 三氟甲磺酸钠 、 碳酸氢钠 、 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(hexafluorophosphate) 、 silver(l) oxide 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以83%的产率得到4-(fluoro)-leu-enkephalin
  参考文献：
  名称：

  Silver-Catalyzed Late-Stage Fluorination

  摘要：

  Carbon-fluorine bond formation by transition metal catalysis is difficult, and only a few methods for the synthesis of aryl fluorides have been developed. All reported transition-metal-catalyzed fluorination reactions for the synthesis of functionalized arenes are based on palladium. Here we present silver catalysis for carbon-fluorine bond formation. Our report is the first example of the use of the transition metal silver to form carbon-heteroatom bonds by cross-coupling catalysis. The functional group tolerance and substrate scope presented here have not been demonstrated for any other fluorination reaction to date.

  DOI：

  10.1021/ja105834t

文献信息

• [EN] FLUORINATION OF ORGANIC COMPOUNDS<br/>[FR] FLUORATION DE COMPOSÉS ORGANIQUES
  申请人：HARVARD COLLEGE

  公开号：WO2010059943A3

  公开（公告）日：2010-09-10
• US9024093B2
  申请人：——

  公开号：US9024093B2

  公开（公告）日：2015-05-05
• Silver-Catalyzed Late-Stage Fluorination
  作者：Pingping Tang、Takeru Furuya、Tobias Ritter

  DOI：10.1021/ja105834t

  日期：2010.9.1

  Carbon-fluorine bond formation by transition metal catalysis is difficult, and only a few methods for the synthesis of aryl fluorides have been developed. All reported transition-metal-catalyzed fluorination reactions for the synthesis of functionalized arenes are based on palladium. Here we present silver catalysis for carbon-fluorine bond formation. Our report is the first example of the use of the transition metal silver to form carbon-heteroatom bonds by cross-coupling catalysis. The functional group tolerance and substrate scope presented here have not been demonstrated for any other fluorination reaction to date.