3-trifluoromethyl-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-trifluoromethyl-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 3-(trifluoromethyl)-2,5-dihydropyrrole-1-carboxylate；tert-butyl 3-(Trifluoromethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate
• 化学式: C₁₀H₁₄F₃NO₂
• 分子量: 237.222
• InChiKey: VYTGKLCSSXKVTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-trifluoromethyl-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 3-(trifluoromethyl)-2,5-dihydro-1H-pyrrole hydrochloride
  参考文献：
  名称：

  [EN] INHIBITORS OF RAF KINASES
  [FR] INHIBITEURS DE KINASES RAF

  摘要：

  本文提供了受体酪氨酸激酶效应子RAF的抑制剂，包括所述化合物的药物组合物，以及使用这些化合物治疗疾病的方法。

  公开号：

  WO2020198058A1
• 作为产物：
  描述：

  叔丁氧基 N-氨基甲酸丙烯 在 tri(cycloxexyl)phosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 14.25h， 生成 3-trifluoromethyl-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles

  摘要：

  A ring-closing metathesis mediated pathway to trifluoromethyl-containing piperidines is detailed. This involves the development of a synthetic route to a new (trifluoromethyl)allylating reagent via a Diels-Alder/retro-Diels-Alder strategy, its application in the synthesis of a series of trifluormethyl-substituted diolefin precursors for ring-closing metathesis, and eventually the successful cyclization of these precursor molecules into the corresponding functionalized piperidines.

  DOI：

  10.1021/jo060893z

文献信息

• [EN] INHIBITORS OF RAF KINASES<br/>[FR] INHIBITEURS DE KINASES RAF
  申请人：KINNATE BIOPHARMA INC

  公开号：WO2020198058A1

  公开（公告）日：2020-10-01

  Provided herein are inhibitors of receptor tyrosine kinase effector, RAF, pharmaceutical compositions comprising said compounds, and methods for using said compounds for the treatment of diseases.

  本文提供了受体酪氨酸激酶效应子RAF的抑制剂，包括所述化合物的药物组合物，以及使用这些化合物治疗疾病的方法。
• [EN] 2-CYANOPYRROLOPYRIMIDINES AND PHARMACEUTICAL USES THEREOF<br/>[FR] 2-CYANOPYRROLOPYRIMIDINES ET UTILISATIONS PHARMACEUTIQUES DE CELLES-CI
  申请人：NOVARTIS AG

  公开号：WO2004069256A1

  公开（公告）日：2004-08-19

  The invention relates to pyrrolo pyrimidines of formula (I), wherein Y represents -(CH2)t-O- or -(CH2)r-S-, p is 1 or 2, r is 1, 2 or 3, t is 1, 2 or 3, or Y is -(CH2)j- or -CH=CH-, j is 1 or 2; p is 1 or 2, or Y is -(CH2)f-, f is 1 or 2, p is 1, and the further radicals and symbols have the meaning as defined herein; their preparation, their use as pharmaceuticals, pharmaceutical compositions containing them, the use of such a compound for the manufacture of a pharmaceutical preparation for the treatment of neuropathic pain and to a method for the treatment of such a disease in animals, especially in humans.

  该发明涉及公式（I）中的吡咯嘧啶，其中Y代表-(CH2)t-O-或-(CH2)r-S-，p为1或2，r为1、2或3，t为1、2或3，或Y为-(CH2)j-或-CH=CH-，j为1或2；p为1或2，或Y为-(CH2)f-，f为1或2，p为1，以及进一步的基团和符号具有如本文所定义的含义；它们的制备，它们作为药物的用途，含有它们的药物组合物，利用这种化合物制备用于治疗神经病性疼痛的药物制剂的用途，以及用于治疗这种疾病的方法在动物中，尤其是在人类中。
• Bicyclic Pyrrolidines for Medicinal Chemistry via [3 + 2]-Cycloaddition
  作者：Vladimir I. Savych、Vladimir L. Mykhalchuk、Pavlo V. Melnychuk、Andrii O. Isakov、Taras Savchuk、Vadim M. Timoshenko、Sergiy A. Siry、Sergiy O. Pavlenko、Dmytro V. Kovalenko、Oleksandr V. Hryshchuk、Vitalii A. Reznik、Bohdan A. Chalyk、Vladimir S. Yarmolchuk、Eduard B. Rusanov、Pavel K. Mykhailiuk

  DOI：10.1021/acs.joc.1c01327

  日期：2021.10.1

  A general approach to bicyclic fused pyrrolidines via [3 + 2]-cycloaddition between nonstabilized azomethyne ylide and endocyclic electron-deficient alkenes was elaborated. “Push–pull” alkenes and CF3-alkenes did not react with the azomethyne ylide under the previously reported conditions, and we developed a superior protocol (LiF, 140 °C, no solvent). Among obtained products were medchem-relevant

  详细阐述了通过不稳定的偶氮甲炔叶立德和环内缺电子烯烃之间的 [3 + 2]-环加成来制备双环稠合吡咯烷的一般方法。在先前报道的条件下，“推拉”烯烃和 CF 3 -烯烃不与偶氮甲炔叶立德反应，我们开发了一种优越的方案（LiF，140 °C，无溶剂）。获得的产品包括与医药相关的双环砜、单氟、二氟和三氟甲基取代的吡咯烷。这种方法不仅允许制备新分子，而且显着简化了现有分子（例如，sofnicline）的合成。
• 2-Cyanopyrrolopyrimidines and pharmaceutical uses thereof
  申请人：Buxton Paul Francis

  公开号：US20060247251A1

  公开（公告）日：2006-11-02

  The invention relates to pyrrolo pyrimidines of formula (I), wherein Y represents —(CH 2 ) t —O— or —(CH 2 ) r —S—, p is 1 or 2, r is 1, 2 or 3, t is 1, 2 or 3, or Y is —(CH 2 ) j — or —CH═CH—, j is 1 or 2; p is 1 or 2, or Y is —(CH 2 ) f —, f is 1 or 2, p is 1, and the further radicals and symbols have the meaning as defined herein; their preparation, their use as pharmaceuticals, pharmaceutical compositions containing them, the use of such a compound for the manufacture of a pharmaceutical preparation for the treatment of neuropathic pain and to a method for the treatment of such a disease in animals, especially in humans.

  本发明涉及式(I)的吡咯吡嗪化合物，其中Y代表—(CH2)t—O—或—(CH2)r—S—，p为1或2，r为1、2或3，t为1、2或3，或Y为—(CH2)j—或—CH═CH—，j为1或2；p为1或2，或Y为—(CH2)f—，f为1或2，p为1，其余基团和符号的含义如本文所定义；制备它们，将它们用作药物，含有它们的制药组合物，使用这种化合物制备治疗神经病痛的药物制剂以及治疗这种疾病的方法，尤其是在动物，特别是人类中。
• Fluorinated (hetero)cycles via ring-closing metathesis of fluoride- and trifluoromethyl-functionalized olefins
  作者：Valeria De Matteis、Floris L. van Delft、René de Gelder、Jörg Tiebes、Floris P.J.T. Rutjes

  DOI：10.1016/j.tetlet.2003.11.093

  日期：2004.1

  Ring-closing metathesis(RCM) has been shown to be a viable tool to incorporate fluoride and trifluoromethyl substituents in (hetero)cyclic ring systems. 2-Fluoroacrylamides were cyclized to the corresponding lactams, and trifluoromethyl- substituted olefins were cyclized to yield trifluoromethylated cyclopentenes, pyrrolines and a dihydrofuran derivative. (C) 2003 Elsevier Ltd. All rights reserved.