4-(2,5-二甲基-1H-吡咯-3-基)苯甲腈 | 138453-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-(2,5-二甲基-1H-吡咯-3-基)苯甲腈
• 英文名称: 4-(2,5-dimethyl-1H-pyrrol-3-yl)benzonitrile
• CAS: 138453-01-7
• 化学式: C₁₃H₁₂N₂
• 分子量: 196.252
• InChiKey: BMSYPCCQNDXLLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,5-二甲基吡咯 、 对氯苯甲腈 在 tris-(dibenzylideneacetone)dipalladium(0) 、 2-二叔丁基膦-2′,4′,6′-三异丙基-3,6-二甲氧基-1,1′-联苯 、 lithium tert-butoxide 作用下， 以 甲苯 为溶剂， 反应 13.0h， 以60%的产率得到4-(2,5-二甲基-1H-吡咯-3-基)苯甲腈
  参考文献：
  名称：

  通过配体控制的位点选择性脱芳香性C2-芳基化和直接C3-芳基化反应合成2,2,5-三取代的2H-吡咯和2,3,5-三取代的1H-吡咯。

  摘要：

  2，5-二芳基-1H-吡咯与芳基氯化物的钯催化的位点选择性脱芳香C2-芳基化反应，合成了一系列的2,2,5-三芳基-2H-吡咯。另外，通过简单地改变配体来改变反应的位点选择性，并制备了直接的C3-芳基化的2,3,5-三芳基-1H-吡咯。所获得的2,2,5-三芳基-2H-吡咯可以进一步转化为2,2,5,5-四芳基吡咯烷。

  DOI：

  10.1021/acs.orglett.9b02559

文献信息

• Use of pyrrole anions as nucleophiles in electrochemically induced SRN1 reactions
  作者：M. Chahma、C. Combellas、H. Marzouk、A. Thiébault

  DOI：10.1016/0040-4039(91)80768-2

  日期：1991.10

  The reactivity of different aryl radicals towards anions of pyrroles is examined under SRN1 conditions. The coupling rate constants are determined by cyclic voltammetry. The corresponding electrolyses are performed using a redox mediator.

  在S RN 1条件下检查了不同芳基对吡咯阴离子的反应性。耦合速率常数通过循环伏安法测定。使用氧化还原介体进行相应的电解。
• Substituted Pyrrole Derivative
  申请人：Matsunaga Nobuyuki

  公开号：US20080176906A1

  公开（公告）日：2008-07-24

  The present invention provides a novel pyrrole derivative having excellent androgen receptor antagonism, which is represented by the formula: wherein R 1 represents a hydrogen atom, a cyano group or a group represented by the formula COOR A (wherein R A represents an optional substituted C 1-6 alkyl group), R 2 and R 4 are the same or different, and each represents a hydrogen atom, a C 1-6 alkyl group, a C 3-6 cycloalkyl group, a trifluoromethyl group, an amino-C 1-6 alkyl group, a mono- or di-substituted amino-C 1-6 alkyl group, an optionally halogenated C 1-6 alkyl group substituted with an optionally substituted hydroxyl group, a C 2-6 alkenyl group substituted with an optionally substituted hydroxyl group, a C 1-6 alkyl group substituted with an optionally substituted and optionally oxidized thiol group, an optionally substituted with and optionally oxidized thiol group, a cyano group, an acyl group, an optionally substituted oxazolyl group or a 1,3-dioxolan-2-yl group, R 3 represents a group represented by the formula: (wherein X represents a halogen atom, Y represents a carbon atom or a nitrogen atom, Alk represents an optionally substituted C 1-4 alkylene group, and R B represents a hydrogen atom or an acyl group), and R 5 represents a phenyl group which has a cyano group at a 4 -position or a 3 -position thereof, and may be further substituted, or a salt thereof. The present invention also provides an androgen receptor antagonist containing the pyrrole derivative, or a salt thereof.

  本发明提供了一种新型吡咯衍生物，具有优异的雄激素受体拮抗作用，其化学式表示为：其中，R1表示氢原子、氰基或由COORA（其中RA表示可选的取代C1-6烷基基团）表示的基团，R2和R4相同或不同，每个表示氢原子、C1-6烷基基团、C3-6环烷基基团、三氟甲基基团、氨基-C1-6烷基基团、单取代或双取代氨基-C1-6烷基基团、可选卤代的C1-6烷基基团，其被取代的羟基基团也是可选的、可选取代的C2-6烯基基团、被可选取代的硫醇基团取代的C1-6烷基基团、被可选取代的、可选氧化的硫醇基团取代的C1-6烷基基团、氰基、酰基、可选取代的噁唑基团或1,3-二氧杂环戊烷-2-基基团，R3表示由以下公式表示的基团：（其中，X表示卤素原子，Y表示碳原子或氮原子，Alk表示可选取代的C1-4烷基基团，RB表示氢原子或酰基），R5表示在其4-位或3-位具有氰基基团的苯基基团，可以进一步取代，或其盐。本发明还提供了一种含有该吡咯衍生物或其盐的雄激素受体拮抗剂。
• Synthesis of multisubstituted pyrroles by ligand-controlled site-selective arylation and their transformation into multiarylated pyrrolines and pyrrolidines
  作者：Miyuki Yamaguchi、Sakiko Fujiwara、Yukiko Mori、Hideyuki Konishi、Kei Manabe

  DOI：10.1016/j.tet.2022.132962

  日期：2022.9

  Multisubstituted pyrroles were prepared by Pd-catalyzed site-selective arylation of 2,5-disubstituted 1H-pyrroles with aryl chlorides, triflates, or nonaflates. Site-selectivity of the reaction was controlled using appropriate ligands, and 2,2,5-trisubstituted 2H-pyrroles were synthesized via dearomative C2-arylation. Moreover, 2,3,5-trisubstituted 1H-pyrroles were successfully fabricated by direct

  多取代的吡咯是通过 Pd 催化的 2,5-二取代的 1 H-吡咯与芳基氯化物、三氟甲磺酸酯或九氟甲磺酸酯的位点选择性芳基化来制备的。使用适当的配体控制反应的位点选择性，并通过脱芳烃 C2-芳基化合成 2,2,5-三取代的 2 H-吡咯。此外，通过直接C3-芳基化成功制备了2,3,5-三取代的1 H-吡咯。这些芳基化可应用于带有芳基氯部分的药物。此外，2,2,5-三芳基-2 H-吡咯被转化为多芳基化吡咯啉和吡咯烷，可用于合成和药物化学。
• Delocalized Nitrogen Carbanions in SRN1 Reactions
  作者：M. Chahma、C. Combellas、A. Thiebault

  DOI：10.1021/jo00129a048

  日期：1995.12

  S(RN)1 reactions can be performed with nitrogen carbanions as nucleophiles, and generally the reaction leads to a mixture of isomers. In the case of the pyrrolyl anion, position 2 is about four times more reactive than position 3. When the ortho positions of pyrrole are substituted by alkyl groups, the reactivity of position 2 increases while that of position 3 decreases. With tert-butyl groups as the substituents, no reaction at position 2 is observed. With the indolyl anion as the nucleophiIe, no substitution at position 2 or at the phenyl ring is observed, and only one product corresponding to monosubstitution at position 3 is obtained. Imidazolyl anions react preferentially at position 4 (5), and substitution of position 2 by a methyl group makes the coupling regioselective.
• SUBSTITUTED PYRROLE DERIVATIVE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1824841A1

  公开（公告）日：2007-08-29