sodium 8-hydroxy-2-methylquinolinate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: sodium 8-hydroxy-2-methylquinolinate
• 英文别名: sodium salt of 2-methylquinolin-8-ol；sodium 2-methylquinolin-8-olate；Sodium;2-methylquinolin-8-olate；sodium;2-methylquinolin-8-olate
• 化学式: C₁₀H₈NO*Na
• 分子量: 181.169
• InChiKey: KWMVCXKCGDYEGA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.38
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  36
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三苯基二氯化铋 、 sodium 8-hydroxy-2-methylquinolinate 以 乙醚 为溶剂， 以70%的产率得到chloro(2-methyl-8-quinolinolato)triphenylbismuth(V)
  参考文献：
  名称：

  苯并铋（III）和三苯并铋（V）与oxine衍生物的配合物。氯（2-甲基-8-喹啉基）三苯基铋（V）的晶体结构

  摘要：

  已制备了配合物Ph 3 Bi（MeOx）X（MeOx = 2-甲基-8-喹啉基; X = Cl，Br），PhBi（MeOx）2和PhBiOx 2（Ox = 8-quinolinolato），并用电子学表征， IR和1 H NMR谱。Ph 3 Bi（MeOx）Cl的晶体结构是根据衍射仪数据通过单晶X射线衍射确定的。晶体数据：C 28 ħ 23 NOClBi，单斜，空间群P 2 1 / Ñ，一个17.05（1），b 13.89（1），Ç 10.51（1），β97.30（3）°，V 2468埃3，ž= 4，D计算为1.70 g cm -3；R = 0.078，观察到3048个反射。络合物是单体的，分子之间的分离良好，金属原子处于扭曲的八面体配位环境中。该金属原子与二齿配体形成一个2.19（2）的BiO键和一个相对弱的2.71（2）的BiN键。

  DOI：

  10.1016/s0022-328x(00)99227-1

文献信息

• Preparation and Reactivity of Some Phenyl-bismuth(III) Quinolin-8-olate Derivatives
  作者：KA Smith、GB Deacon、WR Jackson、JM Miller

  DOI：10.1071/ch9960231

  日期：——

  The bimetallics [ PhBi (Ox)2( NaX )n] (Ox- = quinolin-8-olate: X = Cl , Br or I), containing variable amounts of sodium halides, have been prepared by reaction of PhBiX2 with Na(Ox) (mole ratio 1 : 2) or of Ph2BiX with Na(Ox) (mole ratio 1 : 1) in ethanol. A similar preparation has given [ PhBi ( MeOx )2( NaI )n] ( MeOx - = 2-methylquinolin-8-olate) . The bimetallics have been characterized by X-ray powder photography, f.a.b . mass spectrometry and 1H n.m.r. and electronic spectroscopy. Sodium halide-free PhBi (Ox)2 was obtained from the reaction of Ph2BiCl with Na(Ox) in the presence of 15-crown-5, or from treatment of PhBiI2 or Ph2BiI with NBu4(Ox). Reaction of equimolar amounts of PhBiI2 and Na(Ox) gives Bi(Ox)2I, which can also be obtained from BiI3 and Na(Ox) in a 1:1 or 1:2 stoichiometry. Treatment of PhBiI2 with M(0x) (M = Na or K) in a 1:3 mole ratio yields [ MPhBi (Ox)3] bimetallics, which appear to contain both chelating and unidentate Ox ligands from their electronic spectra.

  含有不同量钠卤化物的双金属化合物[PhBi（Ox）2（NaX）n]（Ox- = 8-喹啉酚酸盐：X = Cl、Br或I）已通过PhBiX2与Na（Ox）（摩尔比1：2）或Ph2BiX与Na（Ox）（摩尔比1：1）在乙醇中反应制备。类似的制备得到了[PhBi（MeOx）2（NaI）n]（MeOx- = 2-甲基喹啉酚酸盐）。这些双金属化合物通过X射线粉末衍射、f.a.b.质谱和1H核磁共振和电子光谱表征。无钠卤化物的PhBi（Ox）2是通过Ph2BiCl与Na（Ox）在15-冠-5存在下反应，或通过处理PhBiI2或Ph2BiI与NBu4（Ox）得到的。PhBiI2和Na（Ox）的等摩尔反应会产生Bi（Ox）2I，也可以通过BiI3和Na（Ox）以1：1或1：2的化学计量法获得。PhBiI2与M（0x）（M = Na或K）在1：3摩尔比下的处理会产生[MPhBi（Ox）3]双金属化合物，从其电子光谱中看出，这些化合物似乎同时含有螯合和单齿的Ox配体。
• Preparation and¹¹⁹Sn NMR Spectra of Coordination Compounds of Di-<i>t</i>-butyltin(IV) Derivatives
  作者：Junzo Otera、Torn Yano、Kazunori Kusakabe

  DOI：10.1246/bcsj.56.1057

  日期：1983.4

  bis(chelates) were prepared and characterized in comparison with dimethyltin analogs. 119Sn NMR spectra show a six-coordinate configuration for the acetylacetonate, tropolonate, and oxinate; a nonchelating structure is partially involved in the 2-methyloxinate and dialkyldithiocarbamates. Di-t-butyltin dichloride gives no isolable adducts with monodentate ligands; however, the Job’s continuous variation

  与二甲基锡类似物相比，制备并表征了二叔丁基锡双（螯合物）。119Sn NMR 光谱显示了乙酰丙酮化物、托酚酸盐和含氧化物的六配位构型；非螯合结构部分地参与到 2-methyloxinate 和二烷基二硫代氨基甲酸酯中。二叔丁基二氯化锡不会产生具有单齿配体的可分离加合物；然而，Job 使用 119Sn NMR 光谱的连续变化方法表明，在醚中发生了 2:1 和/或 1:1 供体/Sn 摩尔比的络合。已经得出结论，叔丁基通过感应和空间效应降低了锡的受体性能。
• Copper(I) binds carbon monoxide in a cubane-like structure: chemistry and X-ray crystal structure of tetrakis[(2-methylquinolin-8-olato)-carbonylcopper(I)]
  作者：M. Pasquali、P. Fiaschi、C. Floriani、P. F. Zanazzi

  DOI：10.1039/c39830000613

  日期：——

  Copper(I) chloride reacts with a solution of sodium 2-methylquinolin-8-olate (qNa) in tetrahydrofuran under a pressure of 60 atm of CO at 65 °C to give a tetranuclear copper(I) carbonyl complex [Cu(q)(CO)]4, (1), [ν(C–O), 2050 cm–1], having a cubane-like structure, with S4 symmetry, in which the copper atoms are bridged by the oxygen atom of the quinolinolato ligand.

  氯化铜（I）与2-甲基喹啉-8-油酸钠（qNa）在四氢呋喃中的溶液在65°C的CO压力为60 atm的条件下反应，生成四核羰基铜（I）羰基配合物[Cu（q） （CO）] 4，（1），[ ν（C–O），2050 cm –1 ]，具有类似S 4对称的类似古巴的结构，其中铜原子被喹啉基上的氧原子桥接配体。
• Homo- and Heteroleptic 8-Quinaldinolate Complexes From Elevated-temperature Rearrangements
  作者：Glen B. Deacon、Peter C. Junk、David R. Turner、Julia A. Walker

  DOI：10.1071/ch13185

  日期：——

  Three new zinc 8-quinaldinolate complexes have been obtained from rearrangement reactions at elevated temperatures including the first homoleptic zinc 8-quinaldinolate complex. The homoleptic, trinuclear complex [Zn3(MQ)6] (1) (MQ = 8-quinaldinolate) was obtained by the recrystallisation of amorphous Zn(MQ)2 from a 1,2,4,5-tetramethylbenzene flux at 270°C. The heteroleptic complexes [Zn4Cl4(MQ)4] (2) and [Zn4Cl2(MQ)6] (3) were simultaneously obtained by the reaction between Zn(MQ)2 and anhydrous ZnCl2 under the same conditions. All complexes contain quinaldinolate ligands in a mixed chelating–bridging coordination mode. The homoleptic complex adopts a V-shaped geometry whereas the heteroleptic complexes adopt closely related cyclic structures.

  在高温下通过重排反应获得了三种新的 8-喹啉酸锌络合物，其中包括第一种同孔 8-喹啉酸锌络合物。在 270°C 的温度下，无定形的 Zn(MQ)2 从 1,2,4,5-四甲基苯通量中重结晶得到了同性三核络合物 [Zn3(MQ)6] (1)（MQ = 8-喹啉酸）。同时，Zn(MQ)2 和无水氯化锌在相同条件下发生反应，得到了[Zn4Cl4(MQ)4](2) 和[Zn4Cl2(MQ)6](3) 两种异质配合物。所有配合物都含有混合螯合桥接配位模式的喹啉配体。同种络合物呈 V 型几何结构，而异种络合物则呈密切相关的环状结构。
• Designing Copper(I) Photosensitizers for the Norbornadiene−Quadricyclane Transformation Using Visible Light:  An Improved Solar Energy Storage System
  作者：Federico Franceschi、Massimo Guardigli、Euro Solari、Carlo Floriani、Angiola Chiesi-Villa、Corrado Rizzoli

  DOI：10.1021/ic9706156

  日期：1997.8.1

  Four copper(I) complexes have been designed as photosensitizers for assisting the norbornadiene (NBD) --> quadricyclene (Q) isomerization with the purpose of carrying out the reaction using visible light and achieving a high NBD/photocatalyst turnover. All complexes contain pi-delocalized bidentate N asymptotic to O monoanionic ligands. Their syntheses have been performed either by the metathesis reaction from CuCl or by reaction of the monoprotic ligands with Cu(5)Mes(5) (Mes = 2,4,6-Me3C6H2) in the presence of norbornadiene. The dinuclear complexes [Cu2L2(mu-NBD)], 3, [Cu2L'(2)(mu-NBD)], 4, [Cu2L ''(2)(mu-NBD)], 5, and [Cu2L'''(2)(mu-NBD)], 6 [where L = 2-methyl-8-oxoquinolinato, L' = 2-methyl-5,7-dichloro-8-oxoquinolinato, L '' = 4-oxoacridinato, and L''' = 2-(2-oxo-3,5-di-tert-butyl phenyl)benzotriazole], have been isolated and characterized in the solid state, including the X-ray analysis on 3 and 6. All compounds show absorption in the visible spectrum, due to the presence of metal-to-ligand charge-transfer (MLCT) bands. Most were active in assisting the NBD --> Q conversion, although the best results were obtained in the case of 3, for which we give a detailed report. Complex 3 is the precursor, in the presence of NBD, of the photoactive monomeric species [CuL(NBD)], 9, where a single C=C binds copper(I), of which complex 7, [CuL(NBN)] [NBN drop norbornene], can be regarded as a model compound. The NBD photoisomerization assisted by 3 (see 9) has been carried out in methanol by visible light irradiation (lambda = 405 nm) with a photoisomerization quantum yield of 0.029. Turnover numbers (moles of Q produced/mole of photocatalyst) of ca. 5000 were obtained: in this solvent. An increase of the temperature gave rise to a significative quantum yield enhancement. The other compounds were less efficient than 3 in assisting the NBD --> Q photoisomerization under visible light irradiation, most probably due to the low energy of their MLCT excited states.