N-(3,3,3-三氟丙基)邻苯二甲酰亚胺 | 347190-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: N-(3,3,3-三氟丙基)邻苯二甲酰亚胺
• 英文名称: 2-(3,3,3-trifluoropropyl)isoindoline-1,3-dione
• 英文别名: n-(3,3,3-Trifluoropropyl)phthalimide；2-(3,3,3-trifluoropropyl)isoindole-1,3-dione
• CAS: 347190-33-4
• 化学式: C₁₁H₈F₃NO₂
• 分子量: 243.185
• InChiKey: AVCRBZGXNDAFND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3,3,3-三氟丙基)邻苯二甲酰亚胺 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 水 、 异丙醇 为溶剂， 反应 26.0h， 以80%的产率得到3,3,3-三氟丙胺盐酸盐
  参考文献：
  名称：

  Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia

  摘要：

  [F-18]-2-(2-Nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide ([F-18]-EF3) has been prepared, in 65% chemical yield and 5% radiochemical yield, by coupling 2,3,5,6-tetrafluorophenyl 2-(2-nitroimidazol-1-yl) acetate 1 with [F-18]-3,3,3-trifluoropropylamine 7. This original radiolabelled key-synthon was obtained in 40% overall chemical yield by oxidative [F-18]-fluorodesulfurization of ethyl N-phthalimido-3-aminopropane dithioate 4, followed by deprotection with hydrazine of the resulting [F-18]-N-phthalimido-3,3,3-trifluoropropylamine 5. All the process was performed within 90 min, from the [F-18]-HF production in the cyclotron to the purification of the final target. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00279-0
• 作为产物：
  描述：

  2-(3-bromoprop-2-yn-1-yl)-isoindoline-1,3-dione 在 氢氟酸 、 五氟化锑 、 吡啶 作用下， 反应 12.17h， 以88%的产率得到N-(3,3,3-三氟丙基)邻苯二甲酰亚胺
  参考文献：
  名称：

  1-溴炔丙基胺在超强酸中的新合成三氟胺

  摘要：

  在HF-SbF 5介质中一步处理1-溴炔丙基胺可得到相应的1,1,1-三氟。根据反应条件，也可以制备1-溴-1,1-二氟或2-溴-1,1,1-三氟衍生物。

  DOI：

  10.1016/j.tetlet.2006.05.123

文献信息

• Starting from Styrene: A Unified Protocol for Hydrotrifluoromethylation of Diversified Alkenes
  作者：Yi-Fei Yang、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1021/acs.orglett.1c03630

  日期：2021.12.3

  In contrast with unactivated alkenes, the corresponding hydrotrifluoromethylation of styrene has remained challenging due to the strong propensity of styrene for oligomerization and polymerization. On the basis of our newly developed trifluoromethylation reagent, TFSP, herein we present a general method for the hydrotrifluoromethylation of styrene under photoredox catalysis. The substrate scope was

  与未活化的烯烃相比，由于苯乙烯具有强烈的低聚和聚合倾向，相应的苯乙烯氢三氟甲基化仍然具有挑战性。在我们新开发的三氟甲基化试剂 TFSP 的基础上，我们提出了一种在光氧化还原催化下苯乙烯氢三氟甲基化的通用方法。底物范围进一步扩展到未活化的烯烃、丙烯酸酯、丙烯酰胺和乙烯基杂原子取代的烯烃。通过相关的去质子三氟甲基化和三氟甲基三氟乙氧基化反应展示了该方法的可调性。
• Trifluoromethylation of Alkyl Radicals in Aqueous Solution
  作者：Haigen Shen、Zhonglin Liu、Pei Zhang、Xinqiang Tan、Zhenzhen Zhang、Chaozhong Li

  DOI：10.1021/jacs.7b06044

  日期：2017.7.26

  The copper-mediated trifluoromethylation of alkyl radicals is described. The combination of Et3SiH and K2S2O8 initiates the radical reactions of alkyl bromides or iodides with BPyCu(CF3)3 (BPy = 2,2'-bipyridine) in aqueous acetone at room temperature to afford the corresponding trifluoromethylation products in good yield. The protocol is applicable to various primary and secondary alkyl halides and

  描述了铜介导的烷基三氟甲基化。Et3SiH 和 K2S2O8 的组合在室温下在丙酮水溶液中引发烷基溴化物或碘化物与 BPyCu(CF3)3（BPy = 2,2'-联吡啶）的自由基反应，以良好的收率提供相应的三氟甲基化产物。该协议适用于各种一级和二级烷基卤化物，并具有广泛的官能团兼容性。提出了一种涉及三氟甲基从 Cu(II)-CF3 中间体转移到烷基自由基的机制。
• Fluorinated Aminoanthraquinone Dyes
  作者：J. B. Dickey、E. B. Towne、M. S. Bloom、G. J. Taylor、D. J. Wallace、John Sagal、M. A. McCall、D. G. Hedberg

  DOI：10.1021/ie50554a018

  日期：1956.2
• METHODS FOR PREPARING PERFLUORINATED [18 F]-RADIOLABELLED NITROIMIDAZOLE DERIVATIVES FOR CELLULAR HYPOXIA DETECTION
  申请人：UNIVERSITE CATHOLIQUE DE LOUVAIN

  公开号：EP1202945B1

  公开（公告）日：2005-08-17
• [EN] METHODS FOR PREPARING PERFLUORINATED [<18>F]-RADIOLABELLED NITROIMIDAZOLE DERIVATIVES FOR CELLULAR HYPOXIA DETECTION<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE NITRO-IMIDAZOLE PERFLUORES RADIOMARQUES AU [<18>F] SERVANT A DETECTER L'HYPOXIE CELLULAIRE
  申请人：UNIV LOUVAIN

  公开号：WO2001012575A1

  公开（公告）日：2001-02-22

  The present invention relates to chemical synthesis of radiolabelled perfluorinated bioactive compounds. More particularly, the present invention relates to radiolabelled compounds to be used as indicators for tissue hypoxia. More particularly, the present invention relates to the synthesis and the use of [18F] labelled perfluorinated nitroimidazole compounds having an incorporation of [18F] atoms characterized by a specific radioactivity of the compound comprised between 1 and 30 Ci/mmol, preferably between 1 and 20 Ci/mmol, preferably 1 and 10 Ci/mmol. More particularly to [18F] labelled EF3 or [18F] labelled EF5. The present invention also relates to a method for the detection of tissue hypoxia in a patient comprising introducing an [18F] labelled nitroimidazole compound into said patient, imaging tissue hypoxia in said patient, and, quantifying tissue hypoxia in said patient.