1-(4-氟苯基)-4-肼基羰基-2-吡咯烷酮 | 669696-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 1-(4-氟苯基)-4-肼基羰基-2-吡咯烷酮
• 英文名称: 1-(4-fluorophenyl)-4-hydrazinocarbonyl-2-pyrrolidinone
• 英文别名: 1-(4-Fluorophenyl)-5-oxopyrrolidine-3-carbohydrazide
• CAS: 669696-68-8
• 化学式: C₁₁H₁₂FN₃O₂
• 分子量: 237.234
• InChiKey: WPTJFEMVIBPOQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 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：
  75.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)-4-肼基羰基-2-吡咯烷酮 在 盐酸 、 potassium hydroxide 、 肼 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 15.0h， 生成 1-(4-fluorophenyl)-4-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-4,5-dihydro-5-thioxo-1H-1,2,4-triazol-3-yl]pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis and Characterization of 4-Substituted 1-(4-Halogenophenyl)pyrrolidin-2-ones with Azole and Azine Moieties

  摘要：

  4-Substituted 1-(4-fluoro- and 4-chlorophenyl)pyrrolidin-2-ones containing azole, oxadiazole, triazole, and triazine fragments have been synthesized, and the characterization of the obtained products is presented. The study compounds have been analyzed by elemental analysis, and the NMR, IR, MS techniques. The H-1/C-13 2D (HETCOR), APT (C-13) NMR methods, and molecular modeling (MM2) were used for structure elucidation in more complicated cases.

  DOI：

  10.3987/com-13-12703
• 作为产物：
  描述：

  1-(4-氟苯基)-5-氧代吡咯烷-3-羧酸 在 硫酸 、 一水合肼 作用下， 以 异丙醇 为溶剂， 反应 6.5h， 生成 1-(4-氟苯基)-4-肼基羰基-2-吡咯烷酮
  参考文献：
  名称：

  Cyclization products of N-fluorophenyl-β-alanines and their properties

  摘要：

  DOI：

  10.1007/s10593-006-0157-4

文献信息

• ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems
  作者：Mikhail A. Kinzhalov、Konstantin V. Luzyanin、Vadim P. Boyarskiy、Matti Haukka、Vadim Yu. Kukushkin

  DOI：10.1021/om4007592

  日期：2013.9.23

  The reaction between the equimolar amounts of cis-[PdCl2(CNR1)(2)] (R-1 = cyclohexyl (Cy) (1), tBu (2)) and the carbohydrazides (RCONHNH2)-C-2 (R-2 = Ph (5), 4-ClC6H4 (6), 3-NO2C6H4 (7), 4-NO2C6H4 (8), 4-CH3C6H4 (9), 3,4-(MeO)(2)C6H3 (10), naphth-1-yl (11), fur-2-yl (12), 4-NO2C6H4CH2 (13), Cy (14), 1-(4-fluorophenyl)-5-oxopyrrolidin-3-yi (15), (pyrrolidin-1-yl)C(0) (16)) proceeds in refluxing CHCl3 for ca. 4 h. A subsequent workup provided the amino-carbene species cis-[PdCl2C(NHNHC(O)R-2)=N(H)R-1}-(CNR1)] (18-33) in good to excellent (80-95%) isolated yields. The coupling of equimolar amounts of cis-[PdCl2(CNR1)(2)] (R-1 = Cy (1), tBu (2), 2,6-Me2C6H3 (XYI) (3), 2-Cl-6-MeC6H3 (4)) and PhSO2NHNH2 (17) occurs similarly and affords the aminocarbenes cis-[PdCl2C(NHNHS(O)(2)Ph)=N(H)R-1}(CNR1)] (34-37; 60-90%). Complexes 18-37 were characterized by elemental analyses (C, H, N), ESV+-MS, IR, and 1D (H-1, C-13H-1}) and 2D (H-1,H-1-COSY, H-1,C-13-HMQC, H-1,C-13-HSQC, HMBC) NMR spectroscopy, as well as by X-ray diffraction for three species (34, 37, and 38). The catalytic properties of 18-37 in Suzuki Miyaura cross-coupling in aqueous medium were evaluated, and 18-37 showed remarkable activity (0.001-0.01 mol % catalyst loading). The scope of the catalytic process covers sterically unhindered and sterically demanding aryl bromides and aryl iodides bearing donor and/or acceptor substituents and activated aryl chlorides. All organohalides reacted with a range of arylboronic acids at 80 degrees C within 2 h (100 degrees C and 3 h for the chlorides), providing target diaryis in yields up to 99% and with maximum TONs of 9.9 X 10(3) (for aryl iodides), 4.7 X 104 (for aryl bromides), and 9.2 X 10(3) (for aryl chlorides).
• Application of palladium complexes bearing acyclic amino(hydrazido)carbene ligands as catalysts for copper-free Sonogashira cross-coupling
  作者：Svetlana A. Timofeeva、Mikhail A. Kinzhalov、Elena A. Valishina、Konstantin V. Luzyanin、Vadim P. Boyarskiy、Tatyana M. Buslaeva、Matti Haukka、Vadim Yu. Kukushkin

  DOI：10.1016/j.jcat.2015.06.001

  日期：2015.9

  Metal-mediated coupling of one isocyanide in cis-[PdCl2(CNR1)(2)] (R-1 = C6H11 (Cy) 1, tBu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3 4) and various carbohydrazides (RCONHNH2)-C-2 [R-2 = Ph 5, 4-ClC6H4 6, 3-NO2C6H4 7, 4-NO2C6H4 8, 4-CH3C6H4 9, 3,4-(MeO)(2)C6H3 10, naphth-1-yl 11, fur-2-yl 12, 4-NO2C6H4CH2 13, Cy 14, 1-(4-fluoropheny1)-5-oxopyrrolidine-3-yl 15, (pyrrolidin-1-yl)C(O) 16, 3-(3,5-di-tert-butyl-4-hydrox yphenyl)propane-1-yl 17, EtNHC(O) 18] or sulfohydrazides (RSO2NHNH2)-S-3 [R-3 = Ph 19, 4-MeC6H4 20] led to a series of (hydrazido)(amino)carbene complexes cis-[PdCl2(C) under bar (NHNHX)=N(H)R-1)(CNR1)1; X = COR2, SO2R3 (21-48, isolated yields 60-96%). All prepared species were characterized by elemental analyses (C, H, N), HR ESI+-MS, IR, H-1 and C-13H-1} NMR spectroscopy, and by a single-crystal X-ray diffraction for 38. Complexes 21-48 demonstrated excellent activity as catalysts in copper-free Sonogashira coupling of aryl iodides and a variety of aromatic terminal alkynes. Catalytic system runs in environmentally benign EtOH ensuring product yields of up to 75-96% and TONs of up to 10(4). Mechanism of the copper-free Sonogashira catalytic cycle involving 21-48 as catalysts was proposed upon identification of key intermediates using HRESI-mass. (C) 2015 Elsevier Inc. All rights reserved.
• Condensation products of 1-aryl-4-hydrazinocarbonyl-2-pyrrolidinones with diketones
  作者：V. Mickevičius、R. Vaickelioniené

  DOI：10.1007/s10593-008-0031-7

  日期：2008.2

  The reactions of 1-aryl-4-hydrazinocarbonyl-2-pyrrolidinones with 2,4-pentanedione and 2,5-hexanedione have been studied. It was found that heating the hydrazinocarbonyl compounds with 2,4-pentanedione gave 3,5-dimethylpyrazole compounds and with 2,5-hexanedione gave 1-substituted 2,5-dimethylpyrroles.
• Cyclization products of N-fluorophenyl-β-alanines and their properties
  作者：R. Vaickelioniene、V. Mickevicius

  DOI：10.1007/s10593-006-0157-4

  日期：2006.6
• Synthesis and Characterization of 4-Substituted 1-(4-Halogenophenyl)pyrrolidin-2-ones with Azole and Azine Moieties
  作者：Vytautas Mickevicius、Rita Vaickelioniene、Gema Mikulskiene

  DOI：10.3987/com-13-12703

  日期：——

  4-Substituted 1-(4-fluoro- and 4-chlorophenyl)pyrrolidin-2-ones containing azole, oxadiazole, triazole, and triazine fragments have been synthesized, and the characterization of the obtained products is presented. The study compounds have been analyzed by elemental analysis, and the NMR, IR, MS techniques. The H-1/C-13 2D (HETCOR), APT (C-13) NMR methods, and molecular modeling (MM2) were used for structure elucidation in more complicated cases.