4-(二甲氧基甲基)-2,6-二甲氧基苯酚 | 66460-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(二甲氧基甲基)-2,6-二甲氧基苯酚
• 英文名称: 4-Hydroxy-3,5-dimethoxy-benzaldehyd-dimethylacetal
• 英文别名: 4-(Dimethoxymethyl)-2,6-dimethoxyphenol
• CAS: 66460-63-7
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: AYYWUJZPRZWBKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(二甲氧基甲基)-2,6-二甲氧基苯酚 在 TEA 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 benzyl [2,6-dimethoxy-4-[(10R,15R,16R)-16-methoxy-12-oxo-13-oxa-8,11-diazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2,4,6-tetraen-10-yl]phenyl] carbonate
  参考文献：
  名称：

  Inhibition of DNA Topoisomerase II by Azaelliptitoxins Functionalized in the Variable Substituent Domain

  摘要：

  A series of novel C-11-substituted derivatives of azaelliptitoxin (azatoxin) have been synthesized and tested for their inhibitory activity against human DNA topoisomerase II. Incorporation of a C-11 polyamine pr amine resulted in an increase in the intercalation properties of the drug and a decrease of topoisomerase II activity. The structure-activity relationship (SAR) profile of the nonintercalating C-11 anilino azatoxin class follows the SAR of the (anilino)acridine family. 11-(4-Cyanoanilino)azatoxin (14) was found to be the most active analog in this series, exhibiting similar to 10-fold higher activity than azatoxin 12 and etoposide.

  DOI：

  10.1021/jm9508806
• 作为产物：
  描述：

  丁香醛 、 原甲酸三甲酯 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以1.37 g的产率得到4-(二甲氧基甲基)-2,6-二甲氧基苯酚
  参考文献：
  名称：

  （+）-聚没食子甲酸酯A和（+）-聚没食子酸酯B的总合成：绝对立体化学和生物遗传意义的阐明。

  摘要：

  （+）-聚没食子内酯A和（+）-聚没食子内酯B的总合成已通过使用羰基内酯环加成策略完成。通过[Rh 2（OAc）4]催化的羰基叶立德形成/分子内1,3-偶极环加成序列。这些天然产物的芳基亚甲基部分是通过甲硅烷基烯醇醚与二甲基乙缩醛的Mukaiyama aldol型反应成功安装的，然后在碱性条件下消除。我们还开发了一种基于杂-迈克尔反应的羰基叶立德前体的替代方法。该方法需要18个步骤，天然产物的总收率为9.8％和9.3％。比较合成材料和天然产物的比旋光度，表明聚果糖苷是通过果糖衍生的氧pyryrylium两性离子与异戊二烯衍生物之间的[5 + 2]环加成而以几乎外消旋的形式生物合成的。

  DOI：

  10.1002/chem.201200542

文献信息

• Transdithioacetalization of acetals, ketals, oximes, enamines and tosylhydrazones catalysed by natural kaolinitic clay
  作者：G. K. Jnaneshwara、N. B. Barhate、A. Sudalai、V. H. Deshpande、R. D. Wakharkar、A. S. Gajare、M. S. Shingare、R. Sukumar

  DOI：10.1039/a706475f

  日期：——

  Natural kaolinitic clay efficiently catalyses the transdithioacetalization of acetals, ketals, oximes, enamines and tosylhydrazones with ethane-1,2-dithiol and propane-1,3-dithiol to produce the corresponding dithiolanes in high yields.

  天然高岭土能高效催化缩醛、缩酮、肟、烯胺和甲苯磺酰腙与乙二硫醇和丙三硫醇的反式双硫缩醛化反应，以高产率生成相应的二硫杂环戊烷。
• Esters are effective co-catalysts in copper-catalyzed methanolysis of aryl bromides
  作者：Patrice Capdevielle、Michel Maumy

  DOI：10.1016/s0040-4039(00)77477-6

  日期：1993.2

  Rate of copper(I)-catalyzed substitution of aryl bromides into methyl-aryl ethers by methoxide ion is greatly enhanced in presence of esters. Soluble copper(I) complexes 2, arising from tetrahedral adducts 1 of methoxide onto esters, are likely responsible for this improvement.

  在酯的存在下，铜（I）催化甲醇盐离子将芳基溴化物取代为甲基-芳基醚的速率大大提高。由甲醇的四面体加成物1生成的可溶性铜（I）配合物2可能是这种改善的原因。
• Novel therapeutic agents that modulate enzymatic processes
  申请人：——

  公开号：US20040023290A1

  公开（公告）日：2004-02-05

  Novel multi-binding compounds are disclosed that modulate enzymatic processes. The compounds of the invention comprise from 2-10 ligands covalently connected, each of said ligands being capable of binding to an enzyme, enzyme substrate or enzyme cofactor thereby modulating the biological processes/functions thereof.

  本发明揭示了一种多重结合化合物，可调节酶过程。该发明的化合物包括2-10个共价连接的配体，每个配体都能够结合到酶、酶底物或酶辅因子上，从而调节其生物过程/功能。
• Catalyst- and Oxidizing Reagent-Free Electrochemical Benzylic C(sp³)–H Oxidation of Phenol Derivatives
  作者：Zhong-Wei Hou、Ming-Ming Zhang、Wen-Chao Yang、Lei Wang

  DOI：10.1021/acs.joc.2c00455

  日期：2022.6.17

  A site-selective electrochemical approach for the benzylic C(sp3)–H oxidation reaction of phenol derivatives along with hydrogen evolution has been developed. The protocol proceeds in an easily available undivided cell at room temperature under catalyst- and oxidizing reagent-free conditions. The corresponding aryl aldehydes and ketones are obtained in satisfactory yields, and the gram-scale synthesis

  已经开发了一种用于苯酚衍生物的苄基 C(sp 3 )-H 氧化反应以及析氢的位点选择性电化学方法。该协议在无催化剂和无氧化剂条件下在室温下在一个容易获得的未分裂电池中进行。相应的芳基醛和酮均以满意的收率得到，且易于进行克级合成。
• Structure-activity relationship for DNA topoisomerase II-induced DNA cleavage by azatoxin analogues
  作者：Jose S. Madalengoitia、Jetze J. Tepe、Karl A. Werbovetz、Erich K. Lehnert、Timothy L. Macdonald

  DOI：10.1016/s0968-0896(97)00113-2

  日期：1997.9

  Eighteen analogues of the nonintercalative DNA topoisomerase II (topo II)-active epipodophyllotoxin-ellipticine hybrid, azatoxin, were synthesized and evaluated for their ability to induce topo II-mediated DNA strand breaks in vitro. In general, the SAR profile of the azatoxins showed more homology with that of the epipodophyllotoxins than with the ellipticines. Of the compounds studied, only fluoro substitution at the 8-, 9, and 10-positions of azatoxins enhanced activity, with 9-fluoroazatoxin being the most active compound in this series. (C) 1997 Elsevier Science Ltd.