4-(4'-decyloxyphenyl)pyridinecarboxylate | 129985-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-(4'-decyloxyphenyl)pyridinecarboxylate
• 英文别名: 4-(octyloxy)phenyl isonicotinate；4-(Decyloxy)phenyl isonicotinate；(4-decoxyphenyl) pyridine-4-carboxylate
• CAS: 129985-84-8
• 化学式: C₂₂H₂₉NO₃
• mdl: MFCD00805668
• 分子量: 355.477
• InChiKey: UUOZEWYUVUCATN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4'-decyloxyphenyl)pyridinecarboxylate 、 以 二氯甲烷 为溶剂， 以89%的产率得到
  参考文献：
  名称：

  Mesogenic Palladium Complexes with Pincer Ligands Derived from Dipicolinic Acid

  摘要：

  4-Substituted pyridine-2,6-dicarboxylic acids, (E)-dipicH(2) and 4-substituted pyridine-2,6-bis(thiocarboxylic) acids, (E)-pdtcH(2), (E = OCnH2n+1, SCnH2n+1) have been synthesized and used as O,N,O- and S,N,S-pincer ligands with palladium. In the fourth coordination site the complexes bear 4-decyloxy-4'-stilbazole (L-1), 4-decyloxy-N-(4-pyridylmethylene)anilines (L-2), decyl 4-pyridinecarboxylate (L-3), 4-(4'-decyloxyphenyl)pyridinecarboxylate (L-4), 4-(3',4',5'-tridecyloxybenzyl)pyridinecarboxylate (L-5), 4-isocyano-1-decyloxybenzene (L-6), or 4-isocyano-4'-decyloxybiphenyl (L-7). Thermotropic mesomorphism is observed for the (E)-dipic complexes with L-5 and n = 12, which display columnar phases. The complexes with S,N,S-pincers show an important depression in the melting point compared to their O,N,O homologues and this change gives rise to mesomorphic materials (Sc). However, in the case of L5 the mesomorphic behavior observed for the O,N,O derivative is lost in its S,N,S analogue. The alkylsulfanyl compounds exhibit lower transition temperatures and wider mesophase ranges than their alkoxy analogues.

  DOI：

  10.1021/ic0001457

文献信息

• Arene ruthenium dichloro complexes containing isonicotinic ester ligands: Synthesis, molecular structure and cytotoxicity
  作者：Farooq-Ahmad Khan、Bruno Therrien、Georg Süss-Fink、Olivier Zava、Paul J. Dyson

  DOI：10.1016/j.jorganchem.2012.10.016

  日期：2013.4

  A series of p-cymene ruthenium dichloro complexes containing isonicotinic ester ligands, [(arene) RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)(n)-CH3] (n = 1: 1, n = 3: 2, n = 5: 3, n = 7:4, n = 9: 5, n = 11: 6, n = 13: 7, n = 15: 8), were prepared from p-cymene ruthenium dichloro dimer and the corresponding isonicotinic ester ligand. The single-crystal X-ray analysis of 1 shows the molecule to adopt the usual pseudo-tetrahedral piano-stool geometry, the isonicotinic ester ligand being coordinated through the nitrogen atom. The cytotoxicity of all complexes and of the free ligands was studied towards human ovarian cancer cells; high activities were observed only for n = 9 (presenting a chain with ten carbon atoms), both as far as the free ligands and the complexes are concerned. Based on this result, a new isonicotinic ester ligand with a C-10 substituent containing a terminal alcohol function, NC5H4-4-COO-C6H4-p-O-(CH2)(10)-OH, was synthesized by a four-step method, and arene ruthenium complexes thereof, [(arene)RuCl2NC5H4-4-COO-C6H4-p-O-(CH2)(10)-OH] (arene = C6H6: 9a, arene = p-MeC6H4Pri: 9b, arene = C6Me6: 9c) were prepared. The complexes 9a and 9b show indeed remarkable anticancer activities, the IC50 values for human ovarian cancer cells being in the submicromolar range. The highest cytotoxicity was observed for complex 9b, with IC50 values of 0.18 mu M for A2780 and 3.04 mu M for the cisplatin-resistant mutant A2780cisR. (C) 2012 Elsevier B.V. All rights reserved.
• Deschenaux, Robert; Donnio, Bertrand; Rheinwald, Gerd, Journal of the Chemical Society, Dalton Transactions, 1997, # 22, p. 4351 - 4355
  作者：Deschenaux, Robert、Donnio, Bertrand、Rheinwald, Gerd、Stauffer, Frederic、Suess-Fink, Georg、Velker, Joerg

  DOI：——

  日期：——
• Dinuclear ruthenium sawhorse-type complexes containing carboxylato bridges and ferrocenyl substituents: Synthesis and electrochemistry
  作者：Mathieu Auzias、Georg Süss-Fink、Petr Štěpnička、Jiří Ludvík

  DOI：10.1016/j.ica.2006.10.020

  日期：2007.4

  The ferrocenyl-containing diruthenium complexes [Ru-2(CO)(4)(mu(2)-eta(2)-OOCFc)(2)L-2] (Fc=ferrocenyl, fc=ferrocen-1,1'-diyl; 1: L=NC5H4-COOC6H4-OC10H21, 2: L=NC5H4-COOC6H4-OC16H33, 3: L=NC5H4-OOC-fc-C12H25) and [Ru-2(CO)(4)(mu(2)-eta(2)- OOC6H5)(2)(NC5H4-OOC-fc-C12H25)(2)] (4) have been synthesized from Ru-3(CO)(12), ferrocene carboxylic or benzoic acid and the corresponding pyridine derivative. The synthesis of the new pyridine derivative NC5H4-OOC-fc-C12H25 used for the preparation of 3 and 4 is also reported. Complexes 1-4 posses a so-called sawhorse structure consisting of the Ru-2(CO)(4) backbone and two bridging carboxylato ligands, while the coordination sphere around the ruthenium atoms is completed by the pyridine-derived ligands bonded in the axial positions. The electrochemical behavior of 1-4 and their known analogues [Ru(CO)(4)(mu(2)-eta(2)-OOCFc)(2)L-2] (5: L = NC5H5, 6: L = P(C6H5)(3), 7: L = NC5H4-OOCFc) has been studied by voltammetry on rotating disc electrode and by cyclic voltammetry. (c) 2006 Elsevier B.V. All rights reserved.
• Mesogenic Palladium Complexes with Pincer Ligands Derived from Dipicolinic Acid
  作者：Pablo Espinet、Esther García-Orodea、Jesús A. Miguel

  DOI：10.1021/ic0001457

  日期：2000.8.1

  4-Substituted pyridine-2,6-dicarboxylic acids, (E)-dipicH(2) and 4-substituted pyridine-2,6-bis(thiocarboxylic) acids, (E)-pdtcH(2), (E = OCnH2n+1, SCnH2n+1) have been synthesized and used as O,N,O- and S,N,S-pincer ligands with palladium. In the fourth coordination site the complexes bear 4-decyloxy-4'-stilbazole (L-1), 4-decyloxy-N-(4-pyridylmethylene)anilines (L-2), decyl 4-pyridinecarboxylate (L-3), 4-(4'-decyloxyphenyl)pyridinecarboxylate (L-4), 4-(3',4',5'-tridecyloxybenzyl)pyridinecarboxylate (L-5), 4-isocyano-1-decyloxybenzene (L-6), or 4-isocyano-4'-decyloxybiphenyl (L-7). Thermotropic mesomorphism is observed for the (E)-dipic complexes with L-5 and n = 12, which display columnar phases. The complexes with S,N,S-pincers show an important depression in the melting point compared to their O,N,O homologues and this change gives rise to mesomorphic materials (Sc). However, in the case of L5 the mesomorphic behavior observed for the O,N,O derivative is lost in its S,N,S analogue. The alkylsulfanyl compounds exhibit lower transition temperatures and wider mesophase ranges than their alkoxy analogues.