3,4-双(甲氧基甲氧基)苯甲醛 | 6515-06-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3,4-双(甲氧基甲氧基)苯甲醛
• 英文名称: 3,4-bis-methoxymethoxy-benzaldehyde
• 英文别名: 3,4-di(methoxymethoxy)benzaldehyde；3,4-Bis(methoxymethoxy)benzaldehyde
• CAS: 6515-06-6
• 化学式: C₁₁H₁₄O₅
• 分子量: 226.229
• InChiKey: RYTSFSLVJDNOHI-UHFFFAOYSA-N

物化性质

• 溶解度：
  二氯甲烷；

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-双(甲氧基甲氧基)苯甲醛 在 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 反应 10.0h， 生成 (E)-3-(3,4-bis(methoxymethoxy)phenyl)acrylic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Natural Ester Sintenin and Its Synthetic Analogues

  摘要：

  Synthesis of 3-(3,4-dimethoxyphenyl)propyl-3-(3,4-dimethoxyphenyl) propanoate (18), a cytotoxic natural ester, was carried out by a convenient synthetic path with a total yield of 49%. Sixteen of its analogues (19-34) were also prepared. Seventeen unsaturated derivatives of 18, compounds 1-17, were also synthesized to examine the structure-activity relationship of this type of ester. All of the synthetic compounds were passed through the cytotoxicity screenings on human tumor cell lines, such as PC-3, Hela, A549, BEL7404, CNE, and KB. Some of the esters exhibited moderate inhibitory effects on these tumor cell lines. The phenolic derivatives exhibited the highest cytotoxicity among these derivatives, while the unsaturated esters were more cytotoxic than the saturated analogues. Some of the compounds also exhibited inhibition on a-glucosidase.

  DOI：

  10.1021/np0496441
• 作为产物：
  描述：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 以 乙醇 为溶剂， 以obtained in Production Example 11 and 32.20 g of the 3,4-bis(methoxymethoxy)benzaldehyde的产率得到3,4-双(甲氧基甲氧基)苯甲醛
  参考文献：
  名称：

  Anti-ulcer agent comprising chalcone derivative

  摘要：

  本发明涉及一种抗溃疡剂，其包括以下通式I所表示的化合物作为有效成分，以及包含在该通式I所表示的化合物中的一种新的查尔酮衍生物： 其中，X和Y独立地代表氢原子或共同形成单键，R1代表羟基、乙酰氧基、羧甲氧基或甲氧羰基甲氧基，R2代表氢原子、异戊烯基、异戊基或丙基，R3代表羟基或甲氧基，R4代表氢原子、羟基或甲氧基，R5代表氢原子、羟基、甲氧基或异戊基，R6代表羟基、甲氧基或羧甲氧基，R7代表氢原子或甲氧基。

  公开号：

  US05234951A1

文献信息

• DESIGN, SYNTHESIS AND FUNCTIONAL CHARACTERIZATION OF ROTTLERIN ANALOGS
  申请人：KANTHASAMY ANUMANTHA G.

  公开号：US20110112182A1

  公开（公告）日：2011-05-12

  A method of synthesizing rottlerin analogs is described. The synthesis methods described are the first known method of synthesizing rottlerin analogs from commercially-available materials to produce cost effective analogs. Rottlerin analog structures made by the synthesis methods and methods of use for treating a neurological or inflammatory response mediated by protein kinase C (PKC) are further described.

  描述了一种合成罗特林类似物的方法。所描述的合成方法是从商业可获得的材料中合成罗特林类似物的首个已知方法，以生产具有成本效益的类似物。通过这些合成方法制备的罗特林类似物结构以及用于治疗由蛋白激酶C（PKC）介导的神经或炎症反应的方法也进一步描述了。
• Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo
  作者：Julian Hofmann、Shaimaa Fayez、Matthias Scheiner、Matthias Hoffmann、Sabrina Oerter、Antje Appelt‐Menzel、Pamela Maher、Tangui Maurice、Gerhard Bringmann、Michael Decker

  DOI：10.1002/chem.202001264

  日期：2020.6.5

  Herein, the resolution of synthetic racemic sterubin (1 ) into its two enantiomers, (R )‐1 and (S )‐1 , is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC‐ECD coupling. (R )‐1 and (S )‐1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol

  阿尔茨海默病（AD）是一种神经系统疾病，目前尚无预防或治疗方法。类黄酮是具有潜在治疗价值的植物化学物质。先前的研究表明，从加州植物Eriodictyon californicum中分离出的黄烷酮 sterubin 在多项体外试验中是一种有效的神经保护剂。本文描述了将合成外消旋斯特鲁宾 ( 1 ) 拆分为其两种对映体 ( R ) -1和 ( S ) -1 ，该操作已在手性色谱相上进行，并通过 HPLC-ECD 在线进行立体化学归属耦合。 ( R ) -1和 ( S ) -1在体外表现出相当的神经保护作用，没有显着差异。虽然纯立体异构体在甲醇中构型稳定，但在培养基存在下观察到快速外消旋化。我们还确定了提取的斯特鲁宾为其纯 ( S )-对映体。此外，首次在AD小鼠模型中体内研究了sterubin ( 1 )的活性。低剂量的 Sterubin ( 1 ) 对短期和长期记忆表现出显着的积极影响。
• Scope and limitations of the Heck–Matsuda-coupling of phenol diazonium salts and styrenes: a protecting-group economic synthesis of phenolic stilbenes
  作者：Bernd Schmidt、Nelli Elizarov、René Berger、Frank Hölter

  DOI：10.1039/c3ob40420j

  日期：——

  4-Phenol diazonium salts undergo Pd-catalyzed Heck reactions with various styrenes to 4′-hydroxy stilbenes. In almost all cases higher yields and fewer side products were observed, compared to the analogous 4-methoxy benzene diazonium salts. In contrast, the reaction fails completely with 2- and 3-phenol diazonium salts. For these substitution patterns the methoxy-substituted derivatives are superior

  4-苯酚重氮盐与各种苯乙烯进行Pd催化的Heck反应，生成4'-羟基苯乙烯。与类似的4-甲氧基苯重氮盐相比，几乎在所有情况下均观察到更高的收率和更少的副产物。相反，用2-和3-苯酚重氮盐使反应完全失败。对于这些取代方式，甲氧基取代的衍生物是优越的。
• Methyl Caffeate as an α-Glucosidase Inhibitor from<i>Solanum torvum</i>Fruits and the Activity of Related Compounds
  作者：Keisuke TAKAHASHI、Yasuyuki YOSHIOKA、Eisuke KATO、Shigeki KATSUKI、Osamu IIDA、Keizo HOSOKAWA、Jun KAWABATA

  DOI：10.1271/bbb.90789

  日期：2010.4.23

  In screening experiments for rat intestinal α-glucosidase (sucrase and maltase) inhibitors in 325 plants cultivated in Japan’s southern island, of Tanegashima, marked inhibition against both sucrase and maltase was found in the extract of the fruit of Solanum torvum. Enzyme-assay guided fractionation of the extract led to the isolation of methyl caffeate (1) as a rat intestinal sucrase and maltase inhibitor. We examined 13 caffeoyl derivatives for sucrase- and maltase-inhibitory activities. The results showed that methyl caffeate (1) had a most favorable structure for both sucrase and maltase inhibition, except for a higher activity of methyl 3,4,5-trihydroxycinnamate (14) against sucrase. Its moderate inhibitory action against α-glucosidase provides a prospect for antidiabetic usage of S. torvum fruit.

  在日本南岛种子岛栽培的325种植物中，筛选大鼠肠道α-葡萄糖苷酶（蔗糖酶和麦芽糖酶）抑制剂的实验发现，茄属植物Solanum torvum果实提取物对蔗糖酶和麦芽糖酶均有显著抑制作用。通过酶活性导向的提取物分级分离，得到了作为大鼠肠道蔗糖酶和麦芽糖酶抑制剂的咖啡酸甲酯（1）。我们检测了13种咖啡酸衍生物对蔗糖酶和麦芽糖酶的抑制活性。结果显示，咖啡酸甲酯（1）在蔗糖酶和麦芽糖酶抑制方面具有最优的结构，除了对蔗糖酶活性更高的3,4,5-三羟基肉桂酸甲酯（14）外。其对α-葡萄糖苷酶的中等抑制作用为Solanum torvum果实的抗糖尿病用途提供了前景。
• Oxoammonium‐Mediated Allylsilane–Ether Coupling Reaction
  作者：Federica Carlet、Greta Bertarini、Gianluigi Broggini、Alexandre Pradal、Giovanni Poli

  DOI：10.1002/ejoc.202100026

  日期：2021.4.22

  An oxoammonium‐mediated α‐C(sp3) allylation of allyl‐ and benzyl ethers using allylsilanes as nucleophilic partners is disclosed. This new C−C bond forming C−H activation process allows to obtain the corresponding coupled products in moderate to good yields.

  公开了使用烯丙基硅烷作为亲核伙伴的烯丙基和苄基醚的氧铵介导的α-C（sp 3）烯丙基化反应。这种新的形成C-H键的C-C键可允许以中等到良好的产率获得相应的偶联产物。