2,3,4-tribromo-5-methoxybenzaldehyde | 1359714-96-7

• 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: 2,3,4-tribromo-5-methoxybenzaldehyde
• CAS: 1359714-96-7
• 化学式: C₈H₅Br₃O₂
• 分子量: 372.839
• InChiKey: BAODNCAONJVLAO-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：

  2,3,4-tribromo-5-methoxybenzaldehyde 在 lithium hydroxide monohydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.17h， 生成 di-tert-butyl propane-1,3-diylbis((3-((E)-3-(2,3,4-tribromo-5-methoxyphenyl)acrylamido)propyl)carbamate)
  参考文献：
  名称：

  海洋天然产物邻苯二甲胺平台上分子库的合成及其生物学评估†

  摘要：

  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

  DOI：

  10.1039/c3ob42537a
• 作为产物：
  描述：

  (2,3,4-tribromo-5-methoxyphenyl)methanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 以94%的产率得到2,3,4-tribromo-5-methoxybenzaldehyde
  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

文献信息

• Intramolecular CH‐Hydrogen Bonding During the Dissociation of the Oxaphosphetane Intermediate Facilitates <i>Z/E</i>‐Selectivity in Wittig Olefination
  作者：Kukkamudi Sreenivas、Chintada Nageswara Rao、Faiz Ahmed Khan

  DOI：10.1002/open.202300171

  日期：2024.3

  The Z-selective synthesis of novel nitrostilbenes has been reported. An intrinsic role of intramolecular hydrogen bonding during the dissociation of OPA-intermediate is critical for the stereoselective Wittig olefination. DFT calculations and X-ray measured intramolecular CH hydrogen bonding distances strongly support the observed phenomenon. Further, the current methodology has been utilized to synthesize

  新型硝基芪的Z选择性合成已有报道。 OPA-中间体解离过程中分子内氢键的内在作用对于立体选择性 Wittig 烯化至关重要。 DFT 计算和 X 射线测量的分子内 CH 氢键距离有力地支持了观察到的现象。此外，目前的方法已用于合成具有药用潜力的水杨酸甲酯基2-芳基吲哚衍生物。
• Synthesis of marine brominated alkaloid amathamide F: a palladium-catalyzed enamide synthesis
  作者：Saeed Ahmad、Sumit Choudhury、Faiz Ahmed Khan

  DOI：10.1016/j.tet.2015.04.091

  日期：2015.6

  Synthesis of brominated marine natural product amathamide F is described. Various strategies to construct the enamide functionality required for its synthesis have been explored. Finally, we succeeded in constructing the enamide moiety under a palladium-catalyzed condition. Facile transformation of 2,3,4-tribromo-5-methoxybenzaldehyde to the reported structure of amathamide F involved initial onecarbon-elongation of the aldehyde group followed by its conversion to corresponding enol acetate derivative prior to crucial Pd(II)-catalyzed cross-coupling with (S)-1-methylpyrrolidine-2-carboxamide. However, due to nonconformity of its NMR spectral data to that of the reported natural isolate, we have confirmed its actual structure through a synthesis. (C) 2015 Elsevier Ltd. All rights reserved.