2,4,6-tribromo-3-methoxybenzaldehyde | 133871-69-9

• 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: 2,4,6-tribromo-3-methoxybenzaldehyde
• 英文别名: 2,4,6-tribromo-5-methoxybenzaldehyde
• CAS: 133871-69-9
• 化学式: C₈H₅Br₃O₂
• 分子量: 372.839
• InChiKey: UFQAZAHRAQNQJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,6-tribromo-3-methoxybenzaldehyde 在 甲烷磺酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 2-(2,4,6-tribromo-3-methoxyphenyl)acetaldehyde
  参考文献：
  名称：

  Synthesis of Reported and Revised Structures of Amathamide D and Synthesis of Convolutamine F, H and Lutamide A, C

  摘要：

  Total synthesis of the published structure of amathamide D is described. Methyl 2,3,4-tribromo-5-hydroxybenzoate was selected as starting compound because it is readily accessible via acid-mediated Grob fragmentation- aromatization reaction of 1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-one. The aforementioned ester was transformed into the reported structure of amathamide D through methylation of a hydroxyl group and conversion of the ester moiety to a beta-aminoethyl side chain. The NMR data of the synthetic compound did not conform to the reported natural product structure possessing contiguously positioned beta-aminoethyl side chain, a set of three adjacent bromines, and a methyl ether linkage on the phenyl ring. This prompted us to redefine the natural product structure by synthesizing a product whose spectral data exactly matched with the reported data of amathamide D. The convolutamine H, with completely substituted phenyl ring adorned with an extra methyl ether functional group, has also been synthesized by application of Grob fragmentation-aromatization strategy to 3-(benzyloxy)-1,4,5,6-tetrabromo-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-one. This approach furnished directly methyl 2,3,4-tribromo-5,6-dimethoxybenzoate, which was converted straightforwardly into convolutamine H. Further, synthesis of convolutamine F and lutamide A and C is also described.

  DOI：

  10.1021/jo3000173
• 作为产物：
  描述：

  间羟基苯甲醛 在 溴 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 2,4,6-tribromo-3-methoxybenzaldehyde
  参考文献：
  名称：

  Amathamides A和B的不对称合成：分离自Amathia wilsoni的新型生物碱

  摘要：

  从塔斯马尼亚分离出的新生物碱类amathamides A和B（（2 S）-N -[（E和Z）-2（2,4-二溴-5-甲氧基苯基乙烯基）-1-甲基-2-吡咯啉羧酰胺）的合成海洋苔藓动物Amathia wilsoni是通过从3-羟基苯甲醛开始的一系列反应完成的。

  DOI：

  10.1016/s0957-4166(02)00586-4

文献信息

• Syntheses of a library of molecules on the marine natural product ianthelliformisamines platform and their biological evaluation
  作者：Faiz Ahmed Khan、Saeed Ahmad、Naveena Kodipelli、Gururaj Shivange、Roy Anindya

  DOI：10.1039/c3ob42537a

  日期：——

  A–C are a novel class of bromotyrosine-derived antibacterial agents isolated recently from the marine sponge Suberea ianthelliformis. We have synthesized ianthelliformisamines A–C straightforwardly by the condensation of (E)-3-(3,5-dibromo-4-methoxyphenyl)acrylic acid and the corresponding Boc-protected polyamine followed by Boc-deprotection with TFA. Further, using this reaction protocol, a library

  Ianthelliformisamines A–C是一类新的从溴酪氨酸衍生的抗菌剂，最近从海洋海绵Suberea ianthelliformis中分离出来。我们通过（E的缩合直接合成了邻苯二甲胺）-3-（3,5-二溴-4-甲氧基苯基）丙烯酸和相应的Boc保护的多胺，然后用TFA进行Boc脱保护。此外，使用该反应方案，通过使用3-苯基丙烯酸衍生物和Boc保护的多胺链，通过这两个片段的不同组合（苯环取代，双键几何结构或链不同），合成了其类似物（39个类似物）的文库多胺链中央间隔基团的长度（以红色显示）。筛选所有合成的化合物（苯乙酰胺胺A–C及其类似物）对革兰氏阴性菌（大肠杆菌）和革兰氏阳性菌（金黄色葡萄球菌）的抗菌活性）株。苯乙酰胺胺A的所有合成类似物均对两种菌株（大肠杆菌和金黄色葡萄球菌）均显示出细菌生长抑制作用，MIC值在117.8–0.10μM范围内，而苯乙酰胺胺C的任何合成类似物以及母
• Total Synthesis of (±)-Cassumunins A–C and Curcumin Analogues
  作者：Faiz Ahmed Khan、Mulla Althafh Hussain

  DOI：10.1055/s-0039-1690794

  日期：2020.5

  cross-coupling reaction. Consequently, the total synthesis of cassumunin C was accomplished in three linear steps from a known alcohol with an overall yield of 53%. The key features involved in this synthesis are tandem [3,3]-sigmatropic shift, SN2′ reaction, and aldol condensation. Moreover, a total of eighteen symmetrical and unsymmetrical curcumin analogues were synthesized.

  给出了（±）-cassumunins A–C（高级抗氧化剂和抗炎剂）的总合成的完整说明。开发了两种新颖的合成cassumunins的方法。cassumunins A和B的总合成过程由已知的醛以五个线性步骤完成，总产率分别为50％和43％，具有级联[3,3]-σ位移（克莱森重排）和Heck交叉偶联反应。因此，从已知的醇以三个线性步骤完成了cassumunin C的总合成，总产率为53％。合成过程中的关键特征是串联[3,3]-向移，S N 2'反应和醛醇缩合。此外，总共合成了十八种对称和不对称姜黄素类似物。
• N -dealkylative S N Ar reaction using aromatic halides: Synthesis of dihydrobenzoxazine and tetrahydrobenzoxazepine derivatives
  作者：Mosim Amin Pathan、Faiz Ahmed Khan

  DOI：10.1016/j.tet.2017.08.047

  日期：2017.10

  An efficient protocol for the synthesis of dihydrobenzoxazine and tetrahydrobenzoxazepine derivatives has been developed using haloarenes involving N-dealkylative SNAr reaction. The method employs a wide variety of substrates and features the formation of CO and CN bonds in one-pot fashion. The products thus generated have been further transformed to m-terphenyls by using Suzuki coupling reaction.

  为二氢苯并恶嗪和tetrahydrobenzoxazep​​ine衍生物的合成的高效协议已经使用涉及卤代芳烃开发Ñ -dealkylative小号Ñ的Ar反应。该方法采用多种底物，并具有一锅法形成C O和C N键的特征。这样产生的产品已进一步转化为米，通过使用Suzuki偶联反应-terphenyls。
• Cu(I)-catalyzed intramolecular cyclization of ene-carbamates: synthesis of indoles and pyrrolo[2,3-c]pyridines
  作者：Claude Barberis、Thomas D. Gordon、Christine Thomas、Xiaolei Zhang、Kevin P. Cusack

  DOI：10.1016/j.tetlet.2005.10.077

  日期：2005.12

  use of palladium-catalyzed aromatic carbon–nitrogen bond forming reactions by the cross-coupling of aryl halides or triflates and amines has become a useful synthetic tool. Herein, we describe a copper(I) catalyst system that allows efficient synthesis of functionalized indoles and pyrrolo[2,3-c]pyridines. This method takes advantage of amino acid promoted copper coupling of amines with aryl halides

  在过去的几年中，通过芳基卤化物或三氟甲磺酸酯和胺的交叉偶联使用钯催化的芳香碳氮键形成反应已成为一种有用的合成工具。在这里，我们描述了一种铜（I）催化剂体系，该体系可以有效合成官能化的吲哚和吡咯并[2,3- c ]吡啶。该方法利用氨基酸促进的胺与芳基卤化物的铜偶联，特别是使用CuI-1-脯氨酸催化剂体系。
• Synthesis and antibacterial activities of marine natural product ianthelliformisamines and subereamine synthetic analogues
  作者：Shivaji Narayan Khadake、Shaik Karamathulla、Tapan Kumar Jena、Mohan Monisha、Nikhil Kumar Tuti、Faiz Ahmed Khan、Roy Anindya

  DOI：10.1016/j.bmcl.2021.127883

  日期：2021.5

  Marine sponges of the genus Suberea produce variety of brominated tyrosine alkaloids which display diverse range of biological activities including antiproliferative, antimicrobial and antimalarial activities. In continuation of our search for biologically active marine natural products for antibacterial compounds, we report here the synthesis and evaluation of biological activity of panel of ianthelliformisamines

  该属的海洋海绵 Suberea 产生多种溴化酪氨酸生物碱，这些生物碱具有多种生物活性，包括抗增殖、抗微生物和抗疟活性。在我们继续寻找具有生物活性的海洋天然产物抗菌化合物的过程中，我们在此报告了使用文献已知的酸-胺偶联反应合成和评估一组花形甲胺和辛二胺类似物的生物活性。通过改变芳族酸衍生物上的溴取代基、胺间隔基以及双键的几何形状，将 Boc 保护的多胺链与溴化芳族丙烯酸衍生物偶联，然后使用 TFA 进行 Boc 脱保护，从而获得了 Ianthelliformisamine 的几种衍生物。相似地，还利用各种溴化苯基丙烯酸与市售手性氨基酯衍生物之间的偶联反应合成了辛二胺类似物，然后进行酯水解。我们筛选了这些合成类似物对革兰氏阴性（大肠杆菌）和革兰氏阳性（金黄色葡萄球菌）菌株的抗菌活性。化合物之一图7c显示了对金黄色葡萄球菌的杀菌活性，IC 50值为3.8 μM（MIC = 25 μM）。