6-(2-hydroxyphenyl)picolinaldehyde | 866613-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(2-hydroxyphenyl)picolinaldehyde
• 英文别名: 6-(2-hydroxyphenyl)pyridine-2-carbaldehyde
• CAS: 866613-66-3
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: WSKBHULLTKDBLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  6-(2-hydroxyphenyl)picolinaldehyde 、 (S)-4-(α-phenylethyl)-semicarbazide 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以51%的产率得到
  参考文献：
  名称：

  四齿双阴离子硫代半碳胺基O ^ N ^ N ^ S配体的Ni，Pd和Pt配合物

  摘要：

  新的四齿酚盐O ^ N ^ N ^ S硫代半碳素（TSC）配体及其Ni（II），Pd（II）和Pt（II）复合物进行了研究。反磁性和正方形平面构型的橙色或红色络合物在非常中等的电势下显示出可逆的还原电化学，部分显示出可逆的氧化电化学。DFT计算显示，基本上以吡啶基-亚胺为中心的最低未占据分子轨道（LUMO），而最高占据分子轨道（HOMO）受酚盐部分，金属d轨道和TSC硫醇盐原子的贡献，与UV-vis光谱电化学保持一致。DFT计算结合红外光谱显示了分子结构的详细信息，通过TD-DFT计算以非常高的准确性对UV-vis吸收进行了建模。UPS与紫外可见吸收和TD-DFT计算数据完全一致，并且显示出Pd> Pt> Ni系列的HOMO-LUMO间隙减小。

  DOI：

  10.1039/d1dt00272d
• 作为产物：
  描述：

  2-甲氧基苯基硼酸 在 四(三苯基膦)钯 、 三溴化硼 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 6-(2-hydroxyphenyl)picolinaldehyde
  参考文献：
  名称：

  苯甲酸酯取代基对带有2-（苯基-2-油酸酯）-6-（1-酰胺基烷基）吡啶钳的铝配合物对ε-己内酯开环聚合的影响

  摘要：

  2-（苯基-2-醇）-6-酮亚氨基吡啶2-（4'-R 1 -C 6 H 3 -2'-OH）-6- {CMe═N（2″，6″ -i）的相互作用-Pr 2 C 6 H 3）} C 5 H 3 N（R 1 = H（L1 a -H），Bu t（L1 b -H），Cl（L1 c -H），F（L1 d -H） ），然后在高温下用AlMe 3结晶，然后从乙腈中结晶，得到五配位的2-（苯基-2-油酸酯）-6-（2-酰胺基丙-2-基）吡啶铝-甲基络合物[2-（4'- [R 1C 6 H 3 -2′-O）-6- {CMe 2 N（2″，6″ -i -Pr 2 C 6 H 3）} C 5 H 3 N] AlMe（NCMe）（R 1 = H（图1A），卜吨（1B），CL（1C），F（1D）），因为它们的乙腈的加合物，以良好的收率。在每种情况下，络合都会通过甲基从铝迁移到L1- H中相应的亚氨基单元而导致伴随的C-

  DOI：

  10.1021/om301057d

文献信息

• Development of homogeneous and heterogenized rhodium(i) and palladium(ii) complexes with ligands based on a chiral proton sponge building block and their application as catalysts
  作者：Gonzalo Villaverde、Avelina Arnanz、Marta Iglesias、Angeles Monge、Félix Sánchez、Natalia Snejko

  DOI：10.1039/c1dt10597c

  日期：——

  chiral ligands for obtaining complexes of rhodium(I) and palladium(II) by reaction with [RhCl(cod)]2, PdCl2(cod) or Pd(OAc)2. The complexes bearing triethoxysilane groups were immobilized on mesoporous MCM-41 in order to obtain new heterogeneous catalysts. Both materials are active in the hydrogenation of alkenes and could be recycled without loss of activity or enantioselectivity.

  由质子海绵结构单元制备的手性化合物 8-（（2 R，5 R）-2,5-二甲基吡咯烷-1-基）萘-1-胺 被发现是有效的手性配体，获得的配合物。 铑（我）和钯（II） 通过与 [RhCl（cod）] 2， PdCl 2（鳕鱼） 或者 钯（OAc）2。复合体轴承三乙氧基硅烷将基团固定在介孔MCM-41上以获得新的非均相催化剂。两种材料在烯烃的氢化中均具有活性，并且可以在不损失活性或对映选择性的情况下进行再循环。
• Organometallic complex luminescent material
  申请人：GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS CO., LTD

  公开号：US11539006B2

  公开（公告）日：2022-12-27

  The present invention relates to an organometal-complex luminescent material which has a structural formula (I), wherein A, B and C refer to substituted or unsubstituted C, N, O and S atoms independently; a dashed ring for linkage between A and B atoms refers to a substituted or unsubstituted conjugated ring structure; L1, L2, L3 and L4 are single bonds or double bonds independently, wherein L3 and L4 are part of the conjugated ring structure for linkage between A and B atoms; X, X1, Y and Y1 are C, N, O and S atoms independently; Ar1 and Ar2 are substituted or unsubstituted conjugated ring structures independently; M refers to Pt, W and Au atoms. An organometal complex in the luminescent material is high in fluorescence quantum efficiency and heat stability and low in quenching constant and can be used for manufacturing high-efficiency and low-efficiency roll-off red-light OLEDs.

  本发明涉及一种有机金属络合物发光材料，它具有结构式（I），其中A、B和C分别指取代或未取代的C、N、O和S原子；用于连接A和B原子的虚线环指取代或未取代的共轭环结构；L1、L2、L3 和 L4 分别是单键或双键，其中 L3 和 L4 是用于连接 A 原子和 B 原子的共轭环结构的一部分；X、X1、Y 和 Y1 分别是 C、N、O 和 S 原子；Ar1 和 Ar2 分别是取代或未取代的共轭环结构；M 是指 Pt、W 和 Au 原子。发光材料中的有机金属复合物具有较高的荧光量子效率和热稳定性，且淬灭常数较低，可用于制造高效率和低效率的滚型红光 OLED。
• Convenient and rapid strategies towards 6-(hetero)aryl pyridylmethylamines: first catalytic issues
  作者：Alexandre Requet、Hasret Yalgin、Damien Prim

  DOI：10.1016/j.tetlet.2015.01.182

  日期：2015.3
• Use of Suzuki cross-coupling as a route to 2-phenoxy-6-iminopyridines and chiral 2-phenoxy-6-(methanamino)pyridines
  作者：Christopher J. Davies、Andrew Gregory、Phillip Griffith、Tom Perkins、Kuldip Singh、Gregory A. Solan

  DOI：10.1016/j.tet.2008.08.019

  日期：2008.10

  The anisyl boronic acids, 2-OMe-3-R-2-5-R-1-C6H2B(OH)(2) (R-1=R-2=H (a); R-1=H, R-2=Ph (b); R-1=Me, R-2=H (c); R-1=Cl, R-2=H (d); R-1=t-Bu, R-2=H (e)), have been employed in Suzuki cross-coupling reactions with either 2-bromo-6-formylpyridine (1) or 2-bromo-6-acetylpyridine (11) generating, following a facile deprotection step, the 2-phenoxy-6-carbonylpyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CH=O)C5H3N (R-1=R-2=H (1a); R-1=Me, R-2=H (1c); R-1=Cl, R-2=H (1d); R-1=t-Bu, R-2=H (1e)) and 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-(CMe=O)C5H3N (R-1=R-2=H (2a); R-1=H, R-2=Ph (2b)). Condensation reactions of 1 and 2 with 2,6-diisopropylaniline proceed smoothly to give the 2-phenoxy-6-iminopyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-CH=N(2,6-i-Pr2C6H3)}C5H3N (R-1=R-2=H (3a); R-1=Me, R-2=H (3c); R-1=Cl, R-2=H (3d); R-1=t-Bu, R-2=H (3e)) and 2-(2'-OH-3'-R-2-5'-R-2-C6H2)-6-CMe=N(2,6-i-Pr2C6H3)}C5H3N (R-1=H, R-2=Ph (4a), R-1=H, R-2=Ph (4b)). Reduction of the imino unit (and concomitant C-C bond formation) in 3 can be achieved by treatment with trimethylaluminium or methyllithium which, following hydrolysis, furnishes the racemic chiral 2-phenoxy-6-(methanamino)pyridines, 2-(2'-OH-3'-R-2-5'-R-1-C6H2)-6-CHMe-NH(2,6-i-Pr2C6H3)}C5H3N R-1=R-2=H (5a); R-1=Me, R-2=H (5c); R-1=Cl, R-2=H (5d); R-1=t-Bu, R-2=H (5e)). This work represents a straightforward and rapid synthetic route to libraries of sterically and electronically variable phenoxy-substituted imino- and methanamino-pyridines, which are expected to act as useful ligands or proligands for late and early transition metal-mediated alkene polymerisation catalysis. (C) 2008 Elsevier Ltd. All rights reserved.
• DEVICE COMPRISING ORGANOMETALLIC COMPLEX LUMINESCENT MATERIAL
  申请人：GUANGDONG AGLAIA OPTOELECTRONIC MATERIALS CO., LTD

  公开号：US20200287085A1

  公开（公告）日：2020-09-10

  A device containing an organometal-complex luminescent material has a luminescent layer that includes an organometal complex having a structural formula (I), wherein A, B and C refer to substituted or unsubstituted C, N, O and S atoms independently; a dashed ring for linkage between A and B atoms refers to a substituted or unsubstituted conjugated ring structure; L1, L2, L3 and L4 are single or double bonds independently, L3 and L4 are part of the conjugated ring structure for linkage between A and B atoms; X, X1, Y and Y1 are C, N, O and S atoms independently; Ar1 and Ar2 are substituted or unsubstituted conjugated ring structures independently; M refers to Pt, W and Au atoms. An organometal complex in the luminescent material is high in fluorescence quantum efficiency and heat stability and low in quenching constant and can be used for manufacturing high-efficiency and low-efficiency roll-off red-light OLEDs.