3-(2'-pyridyl)-5-tert-butyl-2-hydroxybenzaldehyde | 160154-68-7

• 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: 3-(2'-pyridyl)-5-tert-butyl-2-hydroxybenzaldehyde
• 英文别名: 5-tert-butyl-2-hydroxy-3-(2'-pyridyl)benzaldehyde；5-tert-butyl-3-(2-pyridyl)-salicylaldehyde；5-tert-butyl-3-pyridyl-salicyaldehyde
• CAS: 160154-68-7
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: HOQJFZFMMORGBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.19
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 3-(2'-pyridyl)-5-tert-butyl-2-hydroxybenzaldehyde 以 乙醇 为溶剂， 反应 4.0h， 以87%的产率得到bis[5'-tert-butyl-3'-(2''-pyridyl)salicylidene]-(S,S)-1,2-cyclohexanediamine
  参考文献：
  名称：

  Binucleating Ligands:  Synthesis of Acyclic Achiral and Chiral Schiff Base−Pyridine and Schiff Base−Phosphine Ligands

  摘要：

  5-tert-Butyl-3-(2'-pyridyl)salicyaldehyde and 5-tert-butyl-3-(diphenylphosphino)salicyaldehyde were synthesized from 4-tert-butylphenol in good overall yields. Condensation of the salicyaldehydes with 2,3-diamino-2,3-dimethylbutane afforded the desired dinucleating Schiff base-pyridine and Schiff base-phosphine ligands, respectively. 5-tert-Butyl-3-(2'-pyridyl) salicyaldehyde reacted with optically active 1,2-diaminocyclohexanes to give chiral dinucleating Schiff base-pyridine ligands.

  DOI：

  10.1021/jo961020f
• 作为产物：
  描述：

  5-叔丁基-2-羟基苯甲醛 在 四(三苯基膦)钯 、 溴 、 sodium acetate 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 84.0h， 生成 3-(2'-pyridyl)-5-tert-butyl-2-hydroxybenzaldehyde
  参考文献：
  名称：

  Binucleating Ligands:  Synthesis of Acyclic Achiral and Chiral Schiff Base−Pyridine and Schiff Base−Phosphine Ligands

  摘要：

  5-tert-Butyl-3-(2'-pyridyl)salicyaldehyde and 5-tert-butyl-3-(diphenylphosphino)salicyaldehyde were synthesized from 4-tert-butylphenol in good overall yields. Condensation of the salicyaldehydes with 2,3-diamino-2,3-dimethylbutane afforded the desired dinucleating Schiff base-pyridine and Schiff base-phosphine ligands, respectively. 5-tert-Butyl-3-(2'-pyridyl) salicyaldehyde reacted with optically active 1,2-diaminocyclohexanes to give chiral dinucleating Schiff base-pyridine ligands.

  DOI：

  10.1021/jo961020f

文献信息

• Mechanism and scope of salen bifunctional catalysts in asymmetric aldehyde and α-ketoester alkylation
  作者：Michael W. Fennie、Erin F. DiMauro、Erin M. O'Brien、Venkatachalam Annamalai、Marisa C. Kozlowski

  DOI：10.1016/j.tet.2005.03.117

  日期：2005.6

  complexes of C2-symmetric Lewis acid/Lewis base salen ligands provide bifunctional activation resulting in rapid rates in the enantioselective addition of diethylzinc to aldehydes (up to 92% ee). Further experiments probed the reactivity of the individual Lewis acid and Lewis base components of the catalyst and established that both moieties are essential for asymmetric catalysis. These catalysts are also

  C 2对称的路易斯酸/路易斯碱塞伦配体的金属配合物提供双功能激活，从而使二乙基锌对醛的对映选择性加成速率加快（最高ee为92％）。进一步的实验探查了催化剂中各个路易斯酸和路易斯碱组分的反应性，并确定这两个部分对于不对称催化都是必不可少的。这些催化剂在将二乙基锌不对称加成到α-酮酸酯中也是有效的。这一发现意义重大，因为单独的α-酮酸酯充当其自身的配体，以加速Et 2的外消旋1,2-羰基加成反应锌与外消旋羰基还原。后者通过金属茂途径进行，并且通常占主要产物。奇异的路易斯酸催化剂不能在这两个竞争路径上加速对映选择性的1，2-加成。然而，双官能氨基塞伦催化剂以优异的收率，完全的化学选择性和良好的对映选择性（高达88％ee）快速提供对映体富集的1,2-加成产物。合成了双功能氨基塞隆的文库，并在该反应中进行了评估。已经在鸦片拮抗剂的合成中证明了α-酮酸酯方法的实用性。
• Template Synthesis, Crystal Structure and Luminescent Properties of Neutral N ₄ O ₃ Tripodal Ln ^III L Complexes (Ln ^III = La ³⁺ , Eu ³⁺ , Gd ³⁺ , Tb ³⁺ , Dy ³⁺ , Ho ³⁺ , Er ³⁺ , Tm ³⁺ or Lu ³⁺ ; H ₃ L = Tris{[3′‐(2′′‐pyridyl)‐5′‐ <i>tert</i> ‐butyl‐2′‐hydroxybenzylidene‐2‐imino]ethyl}amine)
  作者：Wai‐Kwok Wong、Hongze Liang、Jianping Guo、Wai‐Yeung Wong、Wing‐Kit Lo、King‐Fai Li、Kok‐Wai Cheah、Zhongyuan Zhou、Wing‐Tak Wong

  DOI：10.1002/ejic.200300353

  日期：2004.2

  the neutral Schiff-base complex LnIIIL (Ln = La 1, Eu 2, Gd 3, Tb 4, Dy 5, Ho 6, Er 7, Tm 8 and Lu 9; H3L = tris[3′-(2′′-pyridyl)-5′-tert-butyl-2′-hydroxybenzylidene-2-imino]ethyl}amine). The structures of compounds 4−7 were determined by X-ray crystallography. The crystal structure analyses revealed that the Schiff base behaves as a tri-deprotonated heptadentate ligand encapsulating the lanthanide

  在 Ln3+（Ln = La、Eu、Gd、Tb、Dy、Ho、Er、Tm 或 Lu）存在下，三（2-氨基乙基）胺与三当量的 3-(2'-吡啶基)-5-缩合叔丁基-2-羟基苯甲醛在甲醇中得到中性席夫碱络合物 LnIIIL（Ln = La 1、Eu 2、Gd 3、Tb 4、Dy 5、Ho 6、Er 7、Tm 8 和 Lu 9；H3L =三[3'-(2''-吡啶基)-5'-叔丁基-2'-羟基亚苄基-2-亚氨基]乙基}胺)。化合物 4-7 的结构由 X 射线晶体学确定。晶体结构分析表明，席夫碱表现为三去质子化的七齿配体，将镧系金属离子封装在 N4O3 腔内，所有的吡啶基都是悬垂的。溶液光谱数据表明，LnIIIL 配合物在甲醇中保持完整，并作为九配位非电解质存在，镧系金属离子与三足席夫碱的 N4O3 腔和两个溶剂分子配位。还检查了这些镧系元素席夫碱配合物的溶液光致发光特性。(© Wiley-VCH Verlag
• Synthesis of novel dinickel(<scp>II</scp>) and nickel(<scp>II</scp>)–copper(<scp>II</scp>) bimetallic complexes derived from an acyclic dinucleating Schiff base–pyridine ligand
  作者：Fung Lam、Ru-Ji Wang、Thomas C. W. Mak、Kin Shing Chan

  DOI：10.1039/c39940002439

  日期：——

  Novel phenolic bridged dinickel(II) and nickel(II)–copper(II) complexes are synthesized by stepwise metallation of a dinucleating compartmental Schiff base–pyridine ligand.

  通过分步金属化二核室席夫碱吡啶配体，合成了新型酚桥二镍(II)和镍(II)-铜(II)配合物。
• Synthesis of acyclic dinucleating Schiff base-pyridine and schiff base-phosphine ligands
  作者：Fung Lam、Kin Shing Chan

  DOI：10.1016/0040-4039(94)02372-i

  日期：1995.2

  5-tert-butyl-3-pyridyl-salicyaldehyde and 5-tert-butyl-3-diphenylphosphino-salicyaldehyde have been synthesized from 4-tert-butylphenol in good overall yields. Condensation of the salicyaldehydes with 2,3-diamino-2,3-dimethylbutane afforded the desired dinucleating Schiff base-pyridine and Schiff base-phosphine ligands respectively.
• Binucleating Ligands:  Synthesis of Acyclic Achiral and Chiral Schiff Base−Pyridine and Schiff Base−Phosphine Ligands
  作者：Fung Lam、Jia Xi Xu、Kin Shing Chan

  DOI：10.1021/jo961020f

  日期：1996.1.1

  5-tert-Butyl-3-(2'-pyridyl)salicyaldehyde and 5-tert-butyl-3-(diphenylphosphino)salicyaldehyde were synthesized from 4-tert-butylphenol in good overall yields. Condensation of the salicyaldehydes with 2,3-diamino-2,3-dimethylbutane afforded the desired dinucleating Schiff base-pyridine and Schiff base-phosphine ligands, respectively. 5-tert-Butyl-3-(2'-pyridyl) salicyaldehyde reacted with optically active 1,2-diaminocyclohexanes to give chiral dinucleating Schiff base-pyridine ligands.