2-Oxo-2-(pyrrolidin-1-yl)acetohydrazide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Oxo-2-(pyrrolidin-1-yl)acetohydrazide
• 英文别名: 2-oxo-2-pyrrolidin-1-ylacetohydrazide
• 化学式: C₆H₁₁N₃O₂
• mdl: MFCD01986065
• 分子量: 157.172
• InChiKey: PHVBXZUPXHYKEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  75.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-[bis(cyclohexylisocyanide)dichloropalladium(II)] 、 2-Oxo-2-(pyrrolidin-1-yl)acetohydrazide 以 氯仿 为溶剂， 反应 4.0h， 以87%的产率得到
  参考文献：
  名称：

  ADC-Based Palladium Catalysts for Aqueous Suzuki–Miyaura Cross-Coupling Exhibit Greater Activity than the Most Advantageous Catalytic Systems

  摘要：

  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-[PdCl2{C(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-[PdCl2{C(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-13{H-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).

  DOI：

  10.1021/om4007592

文献信息

• 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.
• Process for preparing 1,2,4-triazole-3-carboxamides
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0126326B1

  公开（公告）日：1987-08-05
• US4578479A
  申请人：——

  公开号：US4578479A

  公开（公告）日：1986-03-25