methyl 3,5-diacetoxy-4-methoxy benzoate | 13089-97-9

• 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: methyl 3,5-diacetoxy-4-methoxy benzoate
• 英文别名: Benzoic acid, 3,5-bis(acetyloxy)-4-methoxy-, methyl ester；methyl 3,5-diacetyloxy-4-methoxybenzoate
• CAS: 13089-97-9
• 化学式: C₁₃H₁₄O₇
• 分子量: 282.25
• InChiKey: MVCZQEYADKZPAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3,5-diacetoxy-4-methoxy benzoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 potassium carbonate 作用下， 生成 3,4,5-三甲氧基甲苯
  参考文献：
  名称：

  Ahluwalia,V.K.; Kumar,D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1977, vol. 15B, p. 18 - 20

  摘要：

  DOI：
• 作为产物：
  描述：

  没食子酸甲酯 在 potassium carbonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 methyl 3,5-diacetoxy-4-methoxy benzoate
  参考文献：
  名称：

  糖基烯基硼酸与芳基卤化物的交叉偶联反应：卑尔根素的合成

  摘要：

  一种方便的合成途径使d -glucal和d -galactal频哪醇硼酸酯，以良好的产率分离出来制备达到了。两种频哪醇硼酸酯都在Suzuki–Miyaura交叉偶联条件下进行了一系列交叉偶联反应测试，从而以高分离产率获得了相应的芳基，杂芳基和烯基衍生物。该方法学适用于木瓜素D的吡喃葡萄糖苷部分的正式合成和佛手素的首次全合成。

  DOI：

  10.1002/chem.201304304

文献信息

• Vanadium-Catalyzed Oxidative Intramolecular Coupling of Tethered Phenols: Formation of Phenol-Dienone Products
  作者：Philip H. Gilmartin、Marisa C. Kozlowski

  DOI：10.1021/acs.orglett.0c00577

  日期：2020.4.17

  A mild and efficient method for the vanadium-catalyzed intramolecular coupling of tethered free phenols is described. The corresponding phenol-dienone products are prepared directly in good yields with low catalyst loadings. Electronically diverse tethered phenol precursors are well tolerated, and the catalytic method was effectively applied as the key step in syntheses of three natural products and

  描述了一种温和有效的方法，用于钒催化的分子内偶联的游离酚的偶联。相应的苯酚-二烯酮产品直接以高收率和低催化剂负载量制备。电子多样性的束缚酚前体具有良好的耐受性，催化方法有效地用作了合成三种天然产物和可合成的吗啡烷生物碱前体的关键步骤。
• Synthesis, crystal structure, and growth inhibition of human hepatoma cell (HepG2) of polyphenolic compounds based on gallates
  作者：Zhu-Ping Xiao、Rui-Qin Fang、Lei Shi、Hui Ding、Chen Xu、Hai-Liang Zhu

  DOI：10.1139/v07-107

  日期：2007.11.1

  Seven compounds (1–7) based on gallate were synthesized and characterized by elemental analysis, ¹H NMR, and MS spectra. 2-(3,5-Dibenzyloxy-4-methoxy)phenyl-2-propanol (6) was a new compound. Methyl 3,5-dihydroxy-4-methoxybenzoate (3), methyl 3,5-dibenzyloxy-4-methoxybenzoate (4), 3,5-dibenzyloxy-4-methoxybenzyl alcohol (5), and compound 6 were structurally determined by single-crystal X-ray diffraction for the first time. Crystallographic data for 3: space group P2₁2₁2₁; a = 4.0750(8) Å, b = 7.5880(15) Å, c = 29.802(6) Å; V = 921.5(3) ų; Z = 4. 4: space group P-1; a = 10.068(2) Å, b = 10.499(2) Å, c = 11.388(2) Å; α = 76.84(3)°, β = 66.79(3)°, γ = 64.10(3)°; V = 993.0(3) ų, Z = 2. 5: space group P-1; a = 8.1410(16) Å, b = 8.7590(18) Å, c = 12.879(3) Å; α = 91.66(3)°, β = 94.69(3)°, γ = 91.73(3)°; V = 914.4(3) ų; Z = 2. 6: space group P2₁/c; a = 5.8100(12) Å, b = 15.778(3) Å, c = 23.237(5) Å; β = 96.09(3)°; V = 2118.1(7) ų; Z = 4. All of the seven compounds were evaluated for the inhibition of growth of human hepatoma (HepG2) cells. Comparison with the positive-control 5-fluorouracil (IC₅₀ 51.6 µmol/L), 5 showed stronger cytotoxic activity with an IC₅₀ around 15.3 µmol/L, while IC₅₀ value of 3 was 90.3 µmol/L. The effect of slight structural variations in this series of compounds was found to cause a marked change in their activity against HepG2 cells.Key words: gallates, benzyl alcohol, human hepatoma cells, crystal structure, anti-cancer activities.

  合成了七种基于没食子酸酯的化合物（1-7），并通过元素分析、1H NMR 和 MS 光谱对其进行了表征。2-(3,5-二苄氧基-4-甲氧基)苯基-2-丙醇（6）是一种新化合物。首次通过单晶 X 射线衍射测定了 3,5-二羟基-4-甲氧基苯甲酸甲酯（3）、3,5-二苄氧基-4-甲氧基苯甲酸甲酯（4）、3,5-二苄氧基-4-甲氧基苯甲醇（5）和化合物 6 的结构。3 的晶体数据：空间群 P212121；a = 4.0750(8) Å，b = 7.5880(15) Å，c = 29.802(6) Å；V = 921.5(3) Å3；Z = 4。4：空间群 P-1；a = 10.068(2)埃，b = 10.499(2)埃，c = 11.388(2)埃；α = 76.84(3)°，β = 66.79(3)°，γ = 64.10(3)°；V = 993.0(3) Å3，Z = 2。5：空间群 P-1；a = 8.1410(16) Å，b = 8.7590(18) Å，c = 12.879(3) Å；α = 91.66(3)°，β = 94.69(3)°，γ = 91.73(3)°；V = 914.4(3) Å3；Z = 2。6：空间群 P21/c；a = 5.8100(12)埃，b = 15.778(3)埃，c = 23.237(5)埃；β = 96.09(3)°；V = 2118.1(7)埃3；Z = 4。对所有七种化合物抑制人肝癌（HepG2）细胞生长的能力进行了评估。与阳性对照 5-氟尿嘧啶（IC50 51.6 µmol/L）相比，5 显示出更强的细胞毒性活性，IC50 约为 15.3 µmol/L，而 3 的 IC50 值为 90.3 µmol/L。在这一系列化合物中，发现轻微的结构变化会导致它们对 HepG2 细胞的活性发生显著变化。
• Gadusol, a metabolite from fish eggs
  作者：Patrick T. Grant、Peter A. Plack、Ronald H. Thomson

  DOI：10.1016/s0040-4039(00)92866-1

  日期：1980.1

  Gadusol, a metabolite from the eggs of cod and other fishes, has been identified as 1,4,5-trihydroxy-2-methoxy-5-hydroxymethylcyclohex-1-en-3-one, related to the mycosporines and analogous compounds.

  Gadusol是鳕鱼和其他鱼类卵中的代谢产物，已被确定为1,4,5-三羟基-2-甲氧基-5-羟甲基环己-1-烯-3-酮，与霉菌素和类似化合物有关。
• Asymmetric synthesis of (2S,3R) β-(4-F-3-NO2) phenyl serine, D-(R)-4-methoxy-3,5-bistbutyldimethylsiloxy phenylglycine and their assemblage to C-O-D ring of vancomycin
  作者：Jieping Zhu、Jean-Philippe Bouillon、Girij Pal Singh、Jacqueline Chastanet、René Bengelmans

  DOI：10.1016/0040-4039(95)01409-b

  日期：1995.9

  The asymmetric synthesis of two appropriately functionalized non-proteinogenic amino acids 2 and 3 needed for the total synthesis of vancomycin was described. The assemblage of these amino acids into linear tripeptide followed by biaryl ether formation via intramolecular SNAr reaction led to the fully functionalized C-O-D ring of vancomycin.
• Meuzelaar, Gerrit J.; Van Vliet, Michiel C. A.; Maat, Leendert, European Journal of Organic Chemistry, 1999, # 9, p. 2315 - 2321
  作者：Meuzelaar, Gerrit J.、Van Vliet, Michiel C. A.、Maat, Leendert、Sheldon, Roger A.

  DOI：——

  日期：——