N-(4-(trimethylammonium)phenyl)pent-4-ynamidetrifluoromethanesulfonate

• 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-(4-(trimethylammonium)phenyl)pent-4-ynamidetrifluoromethanesulfonate
• 英文别名: Trifluoromethanesulfonate;trimethyl-[4-(pent-4-ynoylamino)phenyl]azanium；trifluoromethanesulfonate;trimethyl-[4-(pent-4-ynoylamino)phenyl]azanium
• 化学式: CF₃O₃S*C₁₄H₁₉N₂O
• 分子量: 380.388
• InChiKey: MBVVEKDRDMQYCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  94.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(4-(trimethylammonium)phenyl)pent-4-ynamidetrifluoromethanesulfonate 在 氢氟酸 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 水 、 乙腈 为溶剂， 生成 N-(4-[¹⁸F]fluorophenyl)pent-4-ynamide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of a novel radioligand for αvβ3 integrin receptor imaging: [18F]FPPA-c(RGDfK)

  摘要：

  The development of RGD-based antagonist of alpha v beta 3 integrin receptor has enhanced the interest in PET probes to image this receptor for the early detection of cancer, to monitor the disease progression and the response to therapy. In this work, a novel prosthetic group (N-(4-fluorophenyl)pent-4-ynamide or FPPA) for the F-18-labeling of an alpha v beta 3 selective RGD-peptide was successfully prepared. [F-18]FPPA was obtained in three steps with a radiochemical yield of 44% (decay corrected). Conjugation to c(RGDfK(N-3)) by the Cu(II) catalyzed Huisgen azido alkyne cycloaddition provided the [F-18]FPPA-c(RGDfK) with a radiochemical yield of 29% (decay corrected), in an overall synthesis time of 140 min. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.031
• 作为产物：
  描述：

  炔丙基脲 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 N-(4-(trimethylammonium)phenyl)pent-4-ynamidetrifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis and in vitro evaluation of a novel radioligand for αvβ3 integrin receptor imaging: [18F]FPPA-c(RGDfK)

  摘要：

  The development of RGD-based antagonist of alpha v beta 3 integrin receptor has enhanced the interest in PET probes to image this receptor for the early detection of cancer, to monitor the disease progression and the response to therapy. In this work, a novel prosthetic group (N-(4-fluorophenyl)pent-4-ynamide or FPPA) for the F-18-labeling of an alpha v beta 3 selective RGD-peptide was successfully prepared. [F-18]FPPA was obtained in three steps with a radiochemical yield of 44% (decay corrected). Conjugation to c(RGDfK(N-3)) by the Cu(II) catalyzed Huisgen azido alkyne cycloaddition provided the [F-18]FPPA-c(RGDfK) with a radiochemical yield of 29% (decay corrected), in an overall synthesis time of 140 min. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.031