5-乙酰氧基-2-溴-4-甲氧基苯甲醛 | 69048-79-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 5-乙酰氧基-2-溴-4-甲氧基苯甲醛
• 英文名称: 4-bromo-5-formyl-2-methoxyphenyl acetate
• 英文别名: 5-acetoxy-2-bromo-4-methoxy-benzaldehyde；5-Acetoxy-2-brom-4-methoxy-benzaldehyd；(4-Bromo-5-formyl-2-methoxyphenyl) acetate
• CAS: 69048-79-9
• 化学式: C₁₀H₉BrO₄
• 分子量: 273.083
• InChiKey: LZPVPZSJDNGVPD-UHFFFAOYSA-N

物化性质

• 沸点：
  329.6±42.0 °C(Predicted)
• 密度：
  1.526±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-乙酰氧基-2-溴-4-甲氧基苯甲醛 在 盐酸 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 54.5h， 生成
  参考文献：
  名称：

  Exploring the Formation and Recognition of an Important G-Quadruplex in a HIF1α Promoter and Its Transcriptional Inhibition by a Benzo[c]phenanthridine Derivative

  摘要：

  Four putative G-quadruplex sequences (PGSs) in the HIF1 alpha promoter and the 5'UTR were evaluated for their G-quadruplex-forming potential using ESI-MS, CD, FRET, DMS footprinting, and a polymerase stop assay. An important G-quadruplex (S1) has been proven to inhibit HIF1 alpha transcription by. blocking AP2 binding. A benzo[c]phenanthridine derivative was found to target the S1 G-quadruplex and induce its conformational conversion from antiparallel to parallel orientation. The transcriptional suppression of HIF1 alpha by this compound was demonstrated using western blotting, Q-RT-PCR, luciferase assay, and ChIP. Our new findings provided a novel strategy for HIF1 alpha regulation and potential insight for cancer therapy.

  DOI：

  10.1021/ja412128w
• 作为产物：
  描述：

  异香兰素 在 溴 、 溶剂黄146 作用下， 生成 5-乙酰氧基-2-溴-4-甲氧基苯甲醛
  参考文献：
  名称：

  ACTION OF BROMINE ON VANILLIN, ISOVANILLIN, AND SOME OF THEIR DERIVATIVES, AND MODIFICATION OF THE DIRECTIVE INFLUENCE OF HYDROXYL IN THESE COMPOUNDS

  摘要：

  DOI：

  10.1021/jo01208a017

文献信息

• Cleavage of the methylenedioxy group with sodium methoxide in dimethyl sulfoxide.
  作者：SHIGERU KOBAYASHI、MASARU KIHARA、YOSHINOBU YAMAHARA

  DOI：10.1248/cpb.26.3113

  日期：——

  The methylenedioxy ring in piperonal (1) and its 6-substituted derivatives (5, 6, 9, and 10) was opened by heating with sodium methoxide in dimethyl sulfoxide to give the phenolic products, isovanillin (4) and its 6-substituted derivatives (7, 8, 11, and 12), respectively. Similarly, the nitro compounds (16 and 19) gave phenolic products (17 and 20, respectively) by this method. However, the ring in the compounds having methyl (compound 21), carboxyl (compound 22), methoxycarbonyl (compound 23), and amide (compound 24) groups instead of the formyl group in 1 could not be opened by this method.

  在二甲基亚砜中，使用甲醇钠加热处理胡椒醛（1）及其6-取代衍生物（5、6、9和10），可分别得到酚类产物异香草醛（4）及其6-取代衍生物（7、8、11和12），这些产物是由甲二氧基环开环生成的。同样地，硝基化合物（16和19）通过这种方法也分别生成了酚类产物（17和20）。然而，对于那些以甲基（化合物21）、羧基（化合物22）、甲氧羰基（化合物23）和酰胺基（化合物24）替代了1中的醛基的化合物，这个方法无法打开它们的环。
• A modified Cu(0)-Cu(I)-mediated Caryl-Caryl Ullmann coupling for the synthesis of biaryls
  作者：Kittisak Yasamut、Jira Jongcharoenkamol、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1016/j.tet.2016.07.063

  日期：2016.10

  A novel Cu(0)-Cu(I)-mediated Caryl-Caryl Ullmann coupling has been successfully developed. The use of Cu(I) salts allowed the reactions to proceed under relatively mild conditions (65 °C in DMSO for 15–72 h). The developed method was compatible with a relatively wide range of functional groups simultaneously present on the aromatic ring of different electronic nature. The aryl halides with an electron-withdrawing

  一种新型的Cu（0）-Cu（I）介导的C芳基-C芳基乌尔曼偶联已成功开发。使用Cu（I）盐可使反应在相对温和的条件下（在DMSO中65°C进行15-72 h）进行。所开发的方法与同时存在于不同电子性质的芳环上的相对广泛的官能团相容。具有与卤化物邻位的吸电子基团或与卤化物间位或对位的给电子基团的芳基卤化物以良好的至优异的产率（高达98％）提供了相应的产物。
• Exploration of Novel Urolithin C Derivatives as Non-Competitive Inhibitors of Liver Pyruvate Kinase
  作者：Umberto Maria Battisti、Leticia Monjas、Fady Akladios、Josipa Matic、Eric Andresen、Carolin H. Nagel、Malin Hagkvist、Liliana Håversen、Woonghee Kim、Mathias Uhlen、Jan Borén、Adil Mardinoğlu、Morten Grøtli

  DOI：10.3390/ph16050668

  日期：——

  The inhibition of liver pyruvate kinase could be beneficial to halt or reverse non-alcoholic fatty liver disease (NAFLD), a progressive accumulation of fat in the liver that can lead eventually to cirrhosis. Recently, urolithin C has been reported as a new scaffold for the development of allosteric inhibitors of liver pyruvate kinase (PKL). In this work, a comprehensive structure–activity analysis of urolithin C was carried out. More than 50 analogues were synthesized and tested regarding the chemical features responsible for the desired activity. These data could pave the way to the development of more potent and selective PKL allosteric inhibitors.

  肝脏丙酮酸激酶是一种脂肪在肝脏中逐渐积累并最终导致肝硬化的疾病，抑制肝脏丙酮酸激酶有助于阻止或逆转非酒精性脂肪肝。最近，有报道称尿石素 C 是开发肝丙酮酸激酶（PKL）异位抑制剂的新支架。本研究对尿石素 C 进行了全面的结构-活性分析。我们合成了 50 多种类似物，并测试了这些类似物所具有的化学特征。这些数据可为开发更强效、更具选择性的 PKL 异位抑制剂铺平道路。
• Synthesis of the diaza analogue of ellagic acid
  作者：Ramesh M. Kanojia、Kwasi A. Ohemeng、Charles F. Schwender、John F. Barrett

  DOI：10.1016/0040-4039(95)01872-f

  日期：1995.11

  The novel diaza analogue 2 of DNA-gyrase inhibitor ellagic acid 1 was synthesized via the Ullmann coupling of methyl 2-bromo-3-nitroveratrate 6 which, in turn, was prepared by a 7-step synthesis from 2-bromopiperonal 10 requiring a contrived, regiospecific 3-nitration as a crucial step. Analogue 2 was two-fold as potent a DNA-Gyrase inhibitor as 1.
• KOBAYASHI SHIGERU; KIHARA MASARU; YAMAHARA YOSHINOBU, CHEM. AND PHARM. BULL., 1978, 62, NO 10, 3113-3116
  作者：KOBAYASHI SHIGERU、 KIHARA MASARU、 YAMAHARA YOSHINOBU

  DOI：——

  日期：——