2-hydroxy-5-(2-butyl)benzaldehyde | 59893-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-5-(2-butyl)benzaldehyde
• 英文别名: 5-(1-methylpropyl)salicylaldehyde；5-sec-butyl-2-hydroxybenzaldehyde；2-hydroxy-5-(1-methylpropyl)-benzaldehyde；5-sek.-Butyl-salicylaldehyd；5-butan-2-yl-2-hydroxybenzaldehyde
• CAS: 59893-28-6
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: KKECZRYVNIFRRC-UHFFFAOYSA-N

物化性质

• 沸点：
  252.8±28.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-(2-butyl)benzaldehyde 在 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2-苯并呋喃甲醛,5-(1-甲基丙基)-
  参考文献：
  名称：

  3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

  摘要：

  Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.

  DOI：

  10.1016/0223-5234(96)85165-8
• 作为产物：
  描述：

  对仲丁基苯酚 、 氯仿 在 sodium hydroxide 作用下， 生成 2-hydroxy-5-(2-butyl)benzaldehyde
  参考文献：
  名称：

  3-Benzo[b]furyl- and 3-benzo[b]thienylaminobutyric acids as GABAB ligands. Synthesis and structure-activity relationship studies

  摘要：

  Baclofen (beta-p-chlorophenyl GABA) is one of the selective agonists for the bicuculline-insensitive GABA(B) receptors. In the search for new compounds that bind to GABA(B) receptors it is very important to clarify the structural requirements. We report the syntheses of and binding studies on various S-heteroaromatic (benzo[b]furan and benzo[b]thiophen)aminobutyric acids. The 4-amino-3-(7-methyl-benzo[b]furan-2-yl)butanoic acid 8g is a potent and specific ligand for GABA(B) receptors, with an IC50 value of 5.4 mu M in the displacement of [H-3]GABA.

  DOI：

  10.1016/0223-5234(96)85165-8

文献信息

• [EN] COMPOUNDS USEFUL FOR THE TREATMENT OF METABOLIC DISORDERS AND SYNTHESIS OF THE SAME<br/>[FR] COMPOSÉS UTILES DANS LE TRAITEMENT DE TROUBLES MÉTABOLIQUES ET LEUR SYNTHÈSE
  申请人：UNIV NORTH CAROLINA

  公开号：WO2014165816A1

  公开（公告）日：2014-10-09

  The present invention provides compounds of Formula (I): wherein variables X, Y, Z and R1 are as described herein. Some of the compounds described herein are glutamate dehydrogenase activators. The invention is also directed to pharmaceutical compositions comprising these compounds, uses of these compounds and compositions in the treatment of metabolic disorders as well as synthesis of the compounds.

  本发明提供了式(I)化合物：其中变量X、Y、Z和R1如本文所述。本文所述的一些化合物是谷氨酸脱氢酶激活剂。本发明还涉及包含这些化合物的药物组合物、这些化合物和组合物在治疗代谢紊乱中的用途以及这些化合物的合成。
• Direct C–H bond arylation of 2-hydroxybenzaldehydes with arylboronic acids via ligand-free palladium catalysis
  作者：Fei Weng、Chengming Wang、Bin Xu

  DOI：10.1016/j.tetlet.2010.02.166

  日期：2010.5

  A mild and efficient ligand-free palladium-catalyzed direct C–H bond arylation reaction was developed to afford 2-hydroxybenzophenones in good to excellent yields from easily available 2-hydroxybenzaldehydes and arylboronic acids. The given reaction provided one of the easiest pathways for accessing 2-hydroxybenzophenones, and a variety of functional groups could be tolerated in this process.

  开发了一种温和而有效的无配体钯催化的直接C H键芳基化反应，可从易于获得的2-羟基苯甲醛和芳基硼酸中获得高至优异收率的2-羟基二苯甲酮。给定的反应为获得2-羟基二苯甲酮提供了最简单的途径之一，在此过程中可以耐受多种官能团。
• Hydrogen bonding properties and intermediate structure of N-(2-carboxyphenyl)salicylidenimine
  作者：Alette G. J. Ligtenbarg、Ronald Hage、Auke Meetsma、Ben L. Feringa

  DOI：10.1039/a809497g

  日期：——

  The hydrogen bonding properties, the nature of the tautomeric structure and dimerization of N-(2-carboxyphenyl)salicylidenimine 1 has been studied. The crystal and molecular structure of 1 has been determined by single-crystal X-ray diffraction analysis. This compound forms a dimer in the solid state, which is held together by two strong intermolecular O–H· · ·O bridges [O(1)· · ·O(2a) = 2.455(1) Å]. This dimeric structure is further stabilized by two intramolecular N–H· · ·O hydrogen bonds [N(1)· · ·O(1) = 2.654(1) and N(1)· · ·O(2) = 2.663(1) Å]. In this way, an eight-membered pseudocycle is created. However, in methanol or acetonitrile solution, no dimerization was observed according to 1H-NMR, IR and UV measurements. It was also found that this compound exists as an intermediate form between a phenol-imine and an o-quinoid structure. In addition, a derivative soluble in chloroform, 2-[2-hydroxy-5-(2-butyl)benzylideneamino]benzoic acid 3, was examined for comparison.

  对 N-(2-羧基苯基)水杨亚胺 1 的氢键性质、同分异构结构的性质和二聚化进行了研究。通过单晶 X 射线衍射分析确定了 1 的晶体和分子结构。该化合物在固态下形成二聚体，并通过两个分子间的强 O-H- -O 桥[O(1)- -O(2a) = 2.455(1) Å]固定在一起。分子内的两个 N-H - -O 氢键[N(1)- -O(1) = 2.654(1) Å 和 N(1)- -O(2) = 2.663(1) Å]进一步稳定了这种二聚结构。这样就形成了一个八元假环。然而，在甲醇或乙腈溶液中，根据 1H-NMR、IR 和 UV 测量，没有观察到二聚现象。研究还发现，这种化合物以介于苯酚-亚胺和邻喹啉结构之间的中间形式存在。此外，研究人员还对一种可溶于氯仿的衍生物 2-[2-羟基-5-（2-丁基）亚苄氨基]苯甲酸 3 进行了比较。
• IRE-1alpha INHIBITORS
  申请人：MannKind Corporation

  公开号：US20140080832A1

  公开（公告）日：2014-03-20

  Compounds which directly inhibit IRE-1α activity in vitro, prodrugs, and pharmaceutically acceptable salts thereof. Such compounds and prodrugs are useful for treating diseases associated with the unfolded protein response and can be used as single agents or in combination therapies.

  直接抑制IRE-1α活性的化合物、前药及其药学上可接受的盐。这些化合物和前药可用于治疗与未折叠蛋白应答相关的疾病，并可作为单一药物或联合治疗的组分。
• COMPOUNDS USEFUL FOR THE TREATMENT OF METABOLIC DISORDERS AND SYNTHESIS OF THE SAME
  申请人：NORTH CAROLINA CENTRAL UNIVERSITY

  公开号：US20160046560A1

  公开（公告）日：2016-02-18

  The present invention provides compounds of Formula (I): wherein variables X, Y, Z and R1 are as described herein. Some of the compounds described herein are glutamate dehydrogenase activators. The invention is also directed to pharmaceutical compositions comprising these compounds, uses of these compounds and compositions in the treatment of metabolic disorders as well as synthesis of the compounds.

  本发明提供了一些式子为(I)的化合物：其中变量X、Y、Z和R1如本文所述。其中一些化合物是谷氨酸脱氢酶激活剂。本发明还涉及包含这些化合物的药物组合物，以及这些化合物和组合物在治疗代谢性疾病方面的用途以及化合物的合成。