methyl 2-bromo-6-hydroxy-4-methoxybenzoate | 460348-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-bromo-6-hydroxy-4-methoxybenzoate
• CAS: 460348-08-7
• 化学式: C₉H₉BrO₄
• 分子量: 261.072
• InChiKey: AILDVAXLAHTJLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  324.0±37.0 °C(Predicted)
• 密度：
  1.573±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-6-hydroxy-4-methoxybenzoate 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (2S,Z)-6-((4S)-2,2-dimethyl-5-(prop-2-yn-1-yl)-1,3-dioxolan-4-yl)-6-((4-methoxybenzyl)oxy)hex-4-en-2-yl 2-bromo-6-hydroxy-4-methoxybenzoate
  参考文献：
  名称：

  Convergent stereospecific synthesis of C292 (or LL-Z1640-2), and hypothemycin. Part 1

  摘要：

  The stereospecific synthesis of the precursors required for the 14-membered ring formation either via an intramolecular Suzuki coupling or via an intermolecular Suzuki coupling followed by a macrolactonisation is herein reported. One-pot Suzuki couplings were here achieved with vinyldisiamylboranes which were generated in situ from the related chiral precursor. The present convergent approach of C292 (or LL-21640-2) and hypothemycin gives a flexible access to related macrolides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00870-5
• 作为产物：
  描述：

  4-甲氧基水杨酸 在 叔丁基锂 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 9.17h， 生成 methyl 2-bromo-6-hydroxy-4-methoxybenzoate
  参考文献：
  名称：

  Convergent stereospecific synthesis of C292 (or LL-Z1640-2), and hypothemycin. Part 1

  摘要：

  The stereospecific synthesis of the precursors required for the 14-membered ring formation either via an intramolecular Suzuki coupling or via an intermolecular Suzuki coupling followed by a macrolactonisation is herein reported. One-pot Suzuki couplings were here achieved with vinyldisiamylboranes which were generated in situ from the related chiral precursor. The present convergent approach of C292 (or LL-21640-2) and hypothemycin gives a flexible access to related macrolides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00870-5

文献信息

• Total Synthesis of the Resorcylic Lactone-Based Kinase Inhibitor L-783277
  作者：Karl-Heinz Altmann、Tatjana Hofmann

  DOI：10.1055/s-2008-1078406

  日期：2008.6

  The total synthesis of the natural product L-783277 (1) has been accomplished based on the convergent assembly of building blocks 9, 10, and 14. Key steps are the Suzuki coupling of olefin 11 and aromatic building block 14, the Mitsunobu-based macrolactonization of seco acid 16, and the allylic oxidation of the macrocyclic triol 2 with polymer-bound IBX. Only one of the two C6′-stereoisomers of 2 provided L-783277 (1) with high selectivity.

  天然产物L-783277（1）的全合成基于模块9、10和14的汇聚式组装得以实现。关键步骤包括烯烃11与芳香模块14的Suzuki偶联、裂解酸16的基于Mitsunobu反应的大环内酯化，以及聚合物负载的IBX对大环三醇2的烯丙位氧化。仅有两种C6′立体异构体中的一种能够高选择性地提供L-783277（1）。
• Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate
  作者：Maciej E. Domaradzki、Xiaochen Liu、Jiye Ong、Gyeongah Yu、Gan Zhang、Ariel Simantov、Eliyahu Perl、Yu Chen

  DOI：10.1016/j.tet.2020.131437

  日期：2020.9

  A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Brønsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods

  报道了三氟乙酸（TfOH）介导的邻炔基芳基酯和乙酸铵（NH 4 OAc）的顺序环化。该反应通过布朗斯台德酸介导的邻位分子内环化反应进行-炔基芳基酯接着乙酸铵参与取代反应，形成异喹啉-1-酮为主要产物。与大多数已知的异喹啉-1-酮合成方法不同，所报道的反应不需要金属催化剂。在少数情况下，获得了区域异构体–异吲哚啉-1-酮与异喹啉-1-酮。还分离了中间体化合物-异色酮-1-酮和异苯并呋喃-1-酮。相互转化实验表明，在布朗斯台德酸诱导的邻炔基芳基酯分子内环化过程中形成的区域异构体。采用这种新方法，可以以中等收率制备天然产物ruprechstyril。
• Design and synthesis of 2‐hydroxyl‐4‐methoxyl‐3‐(3‐methylbut‐2‐en‐1‐yl)‐6‐(4‐phenylbenzoylamino)benzoic acid derivatives as antibacterial agents based on cajaninstilbene acid scaffold hopping
  作者：Chang Zheng、Wen Hou、Jun Liu、Xiao‐Fang Xu、Jing Lin、Ping‐Hua Sun、Wei‐Min Chen

  DOI：10.1002/ddr.21556

  日期：2019.9

  novel structural scaffolds. Cajaninstilbene acid (CSA), which is isolated from pigeonpea leaves, has shown potent antibacterial activity. In this study, a series of 2‐hydroxyl‐4‐methoxyl‐3‐(3‐methylbut‐2‐en‐1‐yl)‐6‐(4‐phenylbenzoylamino)benzoic acid derivatives derived from CSA were designed and synthesized, and their antibacterial activities were evaluated. Several synthesized compounds exhibit better

  在临床上具有重要意义的细菌病原体中，多药耐药性的流行表明，迫切需要开发具有新型结构支架的新型抗菌剂。从木豆叶片中分离出来的卡那斯汀二烯酸（CSA）已显示出强大的抗菌活性。在这项研究中，设计和合成了一系列从CSA衍生出来的2-羟基-4-甲氧基-3-（3-甲基丁-2-烯-1-基）-6（4-苯基苯甲酰氨基）苯甲酸衍生物，并对它们的抗菌活性进行了评估。几种合成的化合物对金黄色葡萄球菌，表皮葡萄球菌和两株耐甲氧西林金黄色葡萄球菌的抗菌活性均优于CSA 。。同时，3- [4,5-二甲基噻唑-2-基] -2-，5-二苯基溴化四氮唑测定的结果表明，活性最高的化合物6u和6v在细菌和正常细胞之间具有良好的选择性。此外，对接研究产生的与6u细菌RNA聚合酶的良好结合暗示了这些合成化合物抗菌活性的可能机制。
• Cajaninstilbene acid analogues as novel quorum sensing and biofilm inhibitors of Pseudomonas aeruginosa
  作者：Zhi-Xing Huang、Jia-Hui Yu、Xing-Jun Xu、Xiao-Fang Xu、Ting Zeng、Jing Lin、Wei-Min Chen

  DOI：10.1016/j.micpath.2020.104414

  日期：2020.11

  opportunistic pathogen Pseudomonas aeruginosa are essential for establishment of chronic and recurrent infection, which are regulated by quorum sensing system. In this study, a set of cajaninstilbene acid analogues were designed and synthesized, and their abilities to inhibit QS and biofilm formation were investigated. Among all the compounds, compounds 3g, 3m and 3o showed potent anti-biofilm activity

  机会病原体铜绿假单胞菌中生物膜的形成和毒力因子的分泌对于建立慢性和复发性感染至关重要，这由群体感应系统调节。在这项研究中，设计和合成了一组卡南斯汀二苯甲酸类似物，并研究了它们抑制QS和生物膜形成的能力。在所有化合物中，化合物3g，3m和3o显示出有效的抗生物膜活性，尤其是3o在50μM时显示出有前途的生物膜抑制活性，生物膜抑制比为49.50±1.35％。构建了三种lacZ报告基因菌株以鉴定化合物3o的作用在不同的QS系统上。化合物3o对lasB-lacZ和pqsA-lacZ的表达以及相应毒力因子的产生均具有抑制作用。因此，预期产生化合物3o作为先导化合物，其抑制铜绿假单胞菌的生物膜形成和QS 。
• Total Synthesis of Paecilomycin B
  作者：Kiyomi Ohba、Masaya Nakata

  DOI：10.1021/acs.orglett.5b00983

  日期：2015.6.19

  Starting from the glucose-derived d-lactone and the functionalized aryl bromide, the first total synthesis of naturally occurring paecilomycin B was achieved via functionalized aryl-beta-C-glycoside synthesis using 2,4,6-triisopropylphenyllithium under Barbier-type reaction conditions and ring-closing metathesis as the key steps.