3-(三氟甲基)吡咯 | 71580-26-2

• 物质功能分类: 有机原料 - 有机氟化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 3-(三氟甲基)吡咯
• 英文名称: 3-trifluoromethyl-1H-pyrrole
• 英文别名: 3-(Trifluoromethyl)pyrrole；3-Trifluormethyl-pyrrol；1H-Pyrrole, 3-(trifluoromethyl)-；3-(trifluoromethyl)-1H-pyrrole
• CAS: 71580-26-2
• 化学式: C₅H₄F₃N
• mdl: MFCD11040740
• 分子量: 135.089
• InChiKey: BOMVFZYVIGUOEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(三氟甲基)吡咯 在 N-甲基吗啉 、 sodium tetrahydroborate 、 potassium phosphate 、 copper(l) iodide 、 nickel(II) sulfate hexahydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 (S)-1-(3-((2-aminopropanamido)methyl)phenyl)-N-benzyl-4-(trifluoromethyl)-1H-pyrrole-2-carboxamide trifluoroacetate
  参考文献：
  名称：

  10.1002/cmdc.202400139

  摘要：

  AbstractProtein arginine methyltransferase (PRMT) 4 (also known as coactivator‐associated arginine methyltransferase 1; CARM1) is involved in a variety of biological processes and is considered as an emerging target class in oncology and other diseases. A successful strategy to identify PRMT substrate‐competitive inhibitors has been to exploit chemical scaffolds able to mimic the arginine substrate. (S)‐Alanine amide moiety is a valuable arginine mimic for the development of potent and selective PRMT4 inhibitors; however, its high hydrophilicity led to derivatives with poor cellular outcomes. Here, we describe the development of PRMT4 inhibitors featuring a central pyrrole core and an alanine amide moiety. Rounds of optimization, aimed to increase lipophilicity and simultaneously preserve the inhibitory activity, produced derivatives that, despite good potency and physicochemical properties, did not achieve on‐target effects in cells. On the other hand, masking the amino group with a NAD(P)H:quinone oxidoreductase 1 (NQO1)‐responsive trigger group, led to prodrugs able to reduce arginine dimethylation of the PRMT4 substrates BRG1‐associated factor 155 (BAF155). These results indicate that prodrug strategies can be successfully applied to alanine‐amide containing PRMT4 inhibitors and provide an option to enable such compounds to achieve sufficiently high exposures in vivo.

  DOI：

  10.1002/cmdc.202400139
• 作为产物：
  描述：

  4-(Trifluoromethyl)pyrrole-3-carboxylic acid 在 barium copper chromite 喹啉 作用下， 反应 0.08h， 以45%的产率得到3-(三氟甲基)吡咯
  参考文献：
  名称：

  改进的3-（三氟甲基）吡咯的合成

  摘要：

  本文描述了由叔丁基（E）-4,4,4,4-三氟丁烯酸酯和甲苯磺酰基甲基异氰酸酯通过脱羧合成4-（1-氟甲基）吡咯-3-羧酸在钡上的产率为45％的方法合成3-（三氟甲基）吡咯。促进了喹啉中的亚铬酸铜。

  DOI：

  10.1016/s0022-1139(00)82239-3

文献信息

• A new synthetic route to 3-polyfluoroalkyl-containing pyrroles
  作者：Elena N. Shaitanova、Igor I. Gerus、Valery P. Kukhar

  DOI：10.1016/j.tetlet.2007.12.048

  日期：2008.2

  A novel approach to 3-polyfluoroalkyl pyrroles is reported based on step by step reactions: 1,2-addition of Me3SiCN to β-alkoxyvinyl polyfluoroalkyl ketones, reduction with LiAlH4 and subsequent hydrolysis with intramolecular cyclization. The hydrolytic instability of various polyfluoroalkyl groups at position 3 of the pyrrole ring was evident and a pathway for the hydrolysis was proposed.

  据报导一种基于逐步反应的3-多氟烷基吡咯的新颖方法：将Me 3 SiCN 1，2-加成至β-烷氧基乙烯基多氟烷基酮，用LiAlH 4还原并随后通过分子内环化进行水解。在吡咯环的3位上的各种多氟烷基的水解不稳定性是明显的，并提出了水解的途径。
• Trifluoromethylierungsreaktionen von CF3I, Te(CF3)2, Sb(CF3)3, Hg(CF3)2, und Cd(CF3)2·D mit furan, Thiophen, Pyrrol und p-Benzochinon [1]
  作者：Dieter Naumann、Jürgen Kischkewitz

  DOI：10.1016/s0022-1139(00)80995-1

  日期：1990.2

  The trifluoromethylation reactions of Cd(CF3)2·glyme, Hg(CF3)2, Sb(CF3)3, CF3I, and Te(CF3)2 with furan, thiophene, pyrrol, and p-benzoquinone are compared under similar conditions. During the photochemical reactions the reactivity increases in the series Cd(CF3)2·glyme < Hg(CF3)2 < Sb(CF3)3 < CF3I < Te(CF3)2. Cd(Cf3)2 complexes do not react to form trifluormethylated compounds either by photóchemical

  Cd（CF 3）2 ·甘醇二甲醚，Hg（CF 3）2，Sb（CF 3）3，CF 3 I和Te（CF 3）2与呋喃，噻吩，吡咯和对苯醌的三氟甲基化反应为在类似条件下进行比较。在光化学反应过程中，反应性按Cd（CF 3）2 ·甘醇二甲
• Gas-phase heteroaromatic substitution. 12. Reaction of free trifluoromethyl cation with simple five-membered heteroarenes in the gas phase
  作者：Roberto Bucci、Giuseppe Laguzzi、Maria Luisa Pompili、Maurizio Speranza

  DOI：10.1021/ja00012a024

  日期：1991.6

  The reactivity features of radiolytically ( 60 Co γ-rays) generated unsolvated trifluoromethyl cation CF 3 + toward pyrrole, N-methylpyrrole, furan, and thiophene have been measured under conditions, i.e. 7 Torr of C 2 H 4 added, ensuring depletion of conccomitant radicalic processes. Experiments have been carried out at atmospheric pressure and in the presence of variable concentrations of a gaseous

  放射分解（60 Co γ 射线）产生的未溶剂化的三氟甲基阳离子 CF 3 + 对吡咯、N-甲基吡咯、呋喃和噻吩的反应性特征已在添加 7 Torr 的 C 2 H 4 的条件下进行测量，确保伴随物的消耗激进的过程。实验是在大气压和不同浓度的气态碱（NMe 3 , 0-5 Torr）存在下进行的。讨论了离子三氟甲基化过程和相关离子中间体随后异构化的机理，并评估了 CF 3 + 离子的固有位置选择性
• Chen, Qing-Yun; Li, Zhan-Ting, Journal of the Chemical Society. Perkin transactions I, 1993, # 6, p. 645 - 648
  作者：Chen, Qing-Yun、Li, Zhan-Ting

  DOI：——

  日期：——
• OGOSEH, XISAYASU;AOYAMA, YASUXIRO;DOI, KEHJO;KUSIDA, YASUXIRO
  作者：OGOSEH, XISAYASU、AOYAMA, YASUXIRO、DOI, KEHJO、KUSIDA, YASUXIRO

  DOI：——

  日期：——