3,4-dimethoxy-5-(phenylethynyl)benzaldehyde | 1627998-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dimethoxy-5-(phenylethynyl)benzaldehyde
• 英文别名: 3,4-Dimethoxy-5-(2-phenylethynyl)benzaldehyde
• CAS: 1627998-35-9
• 化学式: C₁₇H₁₄O₃
• 分子量: 266.296
• InChiKey: WLMRCARTDDPKBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4,5-二甲氧基-3-碘苯甲醛 、 苯乙炔 在 C₂₃H₂₀Cl₄N₄OPd 、 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 3,4-dimethoxy-5-(phenylethynyl)benzaldehyde
  参考文献：
  名称：

  Palladium-ADC complexes as efficient catalysts in copper-free and room temperature Sonogashira coupling

  摘要：

  The metal-mediated coupling between cis-[PdCl2(CNR1)(2)] [R-1 = cyclohexyl (Cy) 1, t-Bu 2, 2,6-Me2C6H3 (Xyl) 3, 2-Cl-6-MeC6H3 4] and hydrazones H2NNCR2R3 [R-2, R-3 = Ph 5; R-2, R-3 = C6H4(OMe-4) 6; R-2/R-3 = 9-fluorenyl 7; R-2 = H, R-3 = C6H4(OH-2) 8] provided carbene complexes cis-[PdCl2{C(N(H)N=CR2R3)N(H)R-1}(CNR1)] (9-24) in good (80-85%) yields. Complexes 9-24 showed high activity [yields up to 99%, and turnover numbers (TONs) up to 3.7 x 10(4)] in the Sonogashira coupling of various aryl iodides with a range of substituted aromatic alkynes without the need of copper co-catalyst. The catalytic procedure runs at 80 degrees C for 1 h in EtOH using K2CO3 as a base. No formation of homocoupling or acetylene decomposition products was observed. Designed copper-free Sonogashira system can also run at room temperature giving target products with yields up to 87% and TONs up to 87. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2014.08.018

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.