phenyl 5-bromo-2-hydroxybenzoate | 10268-63-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: phenyl 5-bromo-2-hydroxybenzoate
• 英文别名: 5-bromo-2-hydroxy-benzoic acid phenyl ester；5-Brom-2-hydroxy-benzoesaeure-phenylester；5-Brom-salicylsaeure-phenylester；phenyl 5-bromosalicylate
• CAS: 10268-63-0
• 化学式: C₁₃H₉BrO₃
• 分子量: 293.117
• InChiKey: IRDJLIBTYFENSX-UHFFFAOYSA-N

物化性质

• 沸点：
  378.5±27.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918290000

反应信息

• 作为反应物：
  描述：

  phenyl 5-bromo-2-hydroxybenzoate 生成 5-溴水杨酸
  参考文献：
  名称：

  ‘Prodigious Riches’: The Wealth of Jamaica Before the American Revolution

  摘要：

  This article determines new estimates for the wealth of Jamaica in 1774. These revisions push up previous calculations by between one-half and two-thirds and demonstrate that Jamaica was the wealthiest colony in British America, both in terms of total wealth and in regard to the wealth of individual colonists. These revised estimates also reinforce the extent to which wealth in the Americas was established on the backs of black slaves. The re-evaluation of Jamaican wealth demonstrates how valuable the West Indies were within the empire and suggests that the customary regional classifications of British American colonies need to be rethought.

  DOI：

  10.1111/1468-0289.00201
• 作为产物：
  描述：

  水杨酸苯酯 在 dipotassium hydrogenphosphate 、 potassium carbonate 、 Lumogen F Orange 240 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 60.0h， 生成 phenyl 5-bromo-2-hydroxybenzoate
  参考文献：
  名称：

  可见光光氧化还原催化从芳基醚到羧酸基团的有效芳基迁移，形成酯。

  摘要：

  通过在环境温度下通过可见光光氧化还原催化的逆向Smiles重排，我们开发了从芳基醚到羧酸基团的高效芳基迁移。在转化过程中避免使用过渡金属以及化学计量的氧化剂和碱。受到这种转化的高效率和C-O键断裂的基本重要性的启发，我们开发了一种新颖的方法来联苯醚的C-O裂解形成两个酚类化合物，如一锅，两锅在温和条件下的一步克级反应。芳基迁移表现出广泛的范围，并且可以用于合成诸如醋醋缩丁醛的药物化合物。初步的机理研究表明，催化循环是通过还原性淬灭途径发生的。

  DOI：

  10.1002/anie.201706597

文献信息

• Integrating Metal-Catalyzed C–H and C–O Functionalization To Achieve Sterically Controlled Regioselectivity in Arene Acylation
  作者：Nicholas A. Serratore、Constance B. Anderson、Grant B. Frost、Truong-Giang Hoang、Steven J. Underwood、Philipp M. Gemmel、Melissa A. Hardy、Christopher J. Douglas

  DOI：10.1021/jacs.8b06476

  日期：2018.8.8

  organometallic chemists is the direct functionalization of the bonds most recurrent in organic molecules: C-H, C-C, C-O, and C-N. An even grander challenge is C-C bond formation when both precursors are of this category. Parallel to this is the synthetic goal of achieving reaction selectivity that contrasts with conventional methods. Electrophilic aromatic substitution (EAS) via Friedel-Crafts acylation

  有机金属化学家的一个主要目标是将有机分子中最常见的键直接官能化：CH、CC、CO 和 CN。当两种前体都属于此类时，更大的挑战是 CC 键的形成。与此并行的是实现与传统方法形成对比的反应选择性的合成目标。通过 Friedel-Crafts 酰化的亲电芳香取代 (EAS) 是合成芳基酮的最著名方法，芳基酮是许多药物、农用化学品、香料、染料和其他商品化学品的常见结构基序。然而，只有当所需的酰化位点与反应的电子控制区域选择性一致时，EAS 合成策略才有效。在此，我们报告了空间控制的区域选择性芳烃酰化与水杨酸酯通过铱催化获得明显取代的二苯甲酮。实验和计算数据表明，一种独特的反应机制将 CO 活化和 CH 活化与单一铱催化剂相结合，无需外源氧化剂或碱。我们公开了对芳烃和酯成分的合成范围的广泛探索，最终以简明的合成强效抗癌剂羟基苯司他汀。
• Heterocyclic isosters of antimycobacterial salicylanilides
  作者：Josef Matyk、Karel Waisser、Kateřina Dražková、Jiří Kuneš、Věra Klimešová、Karel Palát、Jarmila Kaustová

  DOI：10.1016/j.farmac.2005.02.002

  日期：2005.5

  A series of 64 derivatives of substituted heterocyclic analogues of salicylanilides was synthesized. The compounds were evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis, Mycobacterium avium and two strains of Mycobacterium kansasii. For the QSAR study, the combination of Free-Wilson approach with Hansch approach was used. The molecules were separated on the heterocyclic

  合成了一系列64个水杨酰苯胺取代杂环类似物的衍生物。评价了化合物对结核分枝杆菌，鸟分枝杆菌和两种堪萨斯分枝杆菌菌株的体外抗分枝杆菌活性。对于QSAR研究，将Free-Wilson方法与Hansch方法结合使用。分子在杂环和水杨基部分上分离，并且还研究了电子和疏水性质的影响。这些化合物是一组潜在的抗结核药。
• Synthesis, molecular modeling and biological evaluation of PSB as targeted antibiotics
  作者：Kui Cheng、Qing-Zhong Zheng、Jin Hou、Yang Zhou、Chang-Hong Liu、Jing Zhao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2010.02.052

  日期：2010.4

  We described here the design, synthesis, molecular modeling, and biological evaluation of a series of peptide and Schiff bases (PSB) small molecules, inhibitors of Escherichia coli β-Ketoacyl-acyl carrier protein synthase III (ecKAS III). The initial lead compound was reported by us previously, we continued to carry out structure–activity relationship studies and optimize the lead structure to potent

  我们在这里描述了一系列肽和席夫碱（PSB）小分子的设计，合成，分子建模和生物学评估，这些小分子是大肠杆菌β-酮酰基-酰基载体蛋白合酶III（ecKAS III）的抑制剂。最初的先导化合物是我们先前报道的，我们继续进行结构-活性关系研究，并在本研究中优化潜在抑制剂的先导结构。结果表明，N-（2-（3,5-二氯-2-羟基苄叉亚氨基）丙基）-2-羟基苯甲酰胺（1f）和2-羟基-N-（2-（2-羟基-5-碘苄叉亚氨基）丙基）-4-甲基苯甲酰胺（3e）通过结合ecKAS III的Gly152 / Gly209并适合底物通道的口，具有良好的ecKAS III抑制活性和良好的结合亲和力，并且可以作为潜在的抗生素剂，在0.20-3.13μg/ g范围内显示出最低的抑制浓度值。 mL和针对各种细菌的0.39–3.13μg/ mL。
• Mixed anhydrides of carbamic and hydroxamic acids
  申请人：Fuji Photo Film Co., Ltd.

  公开号：US04637902A1

  公开（公告）日：1987-01-20

  A base precursor represented by the following general formula (A) or (B): ##STR1## wherein A.sub.1, A.sub.2, A.sub.5, A.sub.6, A.sub.7, and A.sub.8 each represents a hydrogen atom, an alkyl group, a substituted alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aryl group, a substituted aryl group, an acyl group, or a heterocyclic group, and A.sub.1 and A.sub.2 can combine to form a ring and two of A.sub.5, A.sub.6, A.sub.7, and A.sub.8 can combine to form a ring, A.sub.3 and A.sub.4 each represents a hydrogen atom, an alkyl group, a substituted alkyl group, a cycloalkyl group, or an aralkyl group, and A.sub.3 and A.sub.4 can combine to form a ring or A.sub.3 and A.sub.4 can be a double bond forming an imino group from ##STR2## and X represents a nucleophilic group.

  一种以以下一般式(A)或(B)表示的基本前体：##STR1##其中A.sub.1，A.sub.2，A.sub.5，A.sub.6，A.sub.7和A.sub.8分别代表氢原子、烷基、取代烷基、环烷基、烯基、芳基烷基、芳基、取代芳基、酰基或杂环基，A.sub.1和A.sub.2可以结合形成一个环，A.sub.5、A.sub.6、A.sub.7和A.sub.8中的两个可以结合形成一个环，A.sub.3和A.sub.4分别代表氢原子、烷基、取代烷基、环烷基或芳基烷基，A.sub.3和A.sub.4可以结合形成一个环或A.sub.3和A.sub.4可以是一个双键，从##STR2##形成亚胺基，X代表亲核基团。
• A new group of potential antituberculotics: N-(2-pyridylmethyl)salicylamides and N-(3-pyridylmethyl)salicylamides
  作者：Eva Petrlíková、Karel Waisser、Karel Palát、Jiří Kuneš、Jarmila Kaustová

  DOI：10.2478/s11696-010-0084-9

  日期：2011.1.1

  As a part of our systematic study of antimycobacterially active derivatives of salicylamides, a series of nineteen derivatives of N-(2-pyridylmethyl)salicylamides and N-(3-pyridylmethyl)salicylamides was synthesised. The compounds exhibited in vitro activity against Mycobacterium tuberculosis and M. avium. Their lipophilicity, R M, was measured by thin layer chromatography on silica gel impregnated with trioctadecylsilane and the logarithm of the partition coefficient (octanol-water), logP, was calculated. Both the parameters of lipophilicity correlated. The quantitative relationship between the structure and antimycobacterial activity was calculated. Antimycobacterial activity increased with an increase in lipophilicity. The N-(2-pyridylmethyl)salicylamide derivatives were more active than the derivatives of isomeric N-(3-pyridylmethyl)salicylamides. The geometry of compounds was calculated and the calculation was verified by measuring the length of the hydrogen bond between hydroxyl and carbonyl groups on the salicylic moiety.

  摘要：作为我们系统研究水杨酰胺类抗结核活性衍生物的一部分，合成了一系列19个N-(2-吡啶甲基)水杨酰胺和N-(3-吡啶甲基)水杨酰胺衍生物。这些化合物在体外显示出对结核分枝杆菌和分枝杆菌的活性。通过在三十八烷基硅烷浸渍的硅胶上进行薄层色谱测量它们的亲脂性R M，并计算了分配系数（辛醇-水）的对数值logP。两个亲脂性参数相关。计算了结构与抗结核活性之间的定量关系。随着亲脂性的增加，抗结核活性增强。N-(2-吡啶甲基)水杨酰胺衍生物比同分异构体N-(3-吡啶甲基)水杨酰胺衍生物更活跃。计算了化合物的几何结构，并通过测量水杨酸基团上羟基和羰基之间氢键的长度来验证计算结果。