trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran | 921767-78-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran
• 英文别名: trans-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-<(E)-prop-1-enyl>-2,3-dihydrobenzofuran；1-(4'-hydroxy-3'-methoxyphenyl)-2-methyl-5-(propen-1-yl)-7-methoxycoumaran；dl-Dehydrodiisoeugenol；dehydrodiisoeugenol；(+/-)-licarin A；licarin A；2-methoxy-4-[7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
• CAS: 921767-78-4
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: ITDOFWOJEDZPCF-AATRIKPKSA-N

物化性质

• 沸点：
  452.0±45.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)
• 保留指数：
  2722.9

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以83%的产率得到2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-[l(E)-3-oxopropenyl]benzofuran
  参考文献：
  名称：

  A concise and efficient synthesis of salvinal from isoeugenol via a phenoxenium ion intermediate

  摘要：

  In this letter, we describe how salvinal can be efficiently synthesized from isoeugenol via a phenoxenium ion intermediate by four steps in 23% over all total yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.131
• 作为产物：
  描述：

  反式-3-(4-羟基-3-甲氧基苯基)-2-丙烯-1-醇 在 双氧水 、 三乙基硼氢化锂 、 三乙胺 、 horseradish peroxidase 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 trans-2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran
  参考文献：
  名称：

  Stereoselective Synthesis of 8,9-Licarinediols

  摘要：

  The total synthesis of 8,9-licarinediols was selectively carried out from licarin A, previously obtained by oxidative coupling of (E)-isoeugenol. The corresponding enantiomerically pure (+)- and(-)-licarin A ester derivatives were subjected to Sharpless oxidation to yield the asymmetric C-8, C-9 dihydroxylation products, whose absolute configurations were established by means of the CD and NMR spectroscopic analyses of their Mosher ester derivatives. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00873-5

文献信息

• AhR mediators
  申请人：Krutmann Jean

  公开号：US20090028804A1

  公开（公告）日：2009-01-29

  The invention relates to a method for finding and assessing agonists [and] antagonists of the aryl hydrocarbon receptor (Ah receptor; AhR), to the agonists and antagonists themselves and to uses thereof.

  这项发明涉及一种用于寻找和评估芳香族羟基化合物受体（Ah受体；AhR）的激动剂和拮抗剂的方法，以及这些激动剂和拮抗剂本身及其用途。
• Process for making derivatives of dimers of isoeugenol
  申请人：PLC Pharmaceutical Licenses Co. Ltd.

  公开号：US04256764A1

  公开（公告）日：1981-03-17

  Compounds of formula ##STR1## have liver-protecting properties. They are prepared by reacting dehydro-isoeugenol or di-isoeugenol with an oxazolidine of formula ##STR2##

  式为##STR1##的化合物具有保护肝脏的性质。它们是通过将脱氢异欧芹酚或二异欧芹酚与式为##STR2##的噁唑烷酮反应制备的。
• An efficient and flexible synthesis of model lignin oligomers
  作者：W. Graham Forsythe、Mark D. Garrett、Christopher Hardacre、Mark Nieuwenhuyzen、Gary N. Sheldrake

  DOI：10.1039/c3gc41110a

  日期：——

  The use of model compounds in the development of selective lignin depolymerisation processes has been limited by the lack of complexity of these models compared with lignin itself. In this paper we report a convergent and efficient synthetic method for the flexible, multi-gram preparation of model lignin hexamers and octamers containing three of the most common connectivity motifs found within native lignin, namely β-O-4′, 5-5′ and β-5′, which will be used to further the mechanistic understanding of lignin depolymerisation processes.

  在发展选择性木质素解聚过程方面，模型化合物应用受限，因其复杂性不足，与木质素本身相去甚远。本文中，我们报道了合成模型木质素六聚体和八聚体的集约而高效的方法，可灵活制备多克量产品。模型化合物包含三种最常见的连接模式，即β-O-4′、5-5′和β-5′，这些模式存在于天然木质素中。我们将运用这些模型化合物，进一步深化对木质素解聚过程机理的理解。
• USE OF DIHYDRODEHYDRODIISOEUGENOL AND PREPARATIONS COMPRISING DIHYDRODEHYDRODIISOEUGENOL
  申请人：Meyer Imke

  公开号：US20130101650A1

  公开（公告）日：2013-04-25

  This invention relates to cosmetic and pharmaceutical preparations comprising (i) a diastereomer or a mixture of two or more diastereomers of the compound of formula (I) or (ii) a salt of a diastereomer or of a mixture of two or more diastereomers of the compound of formula (I) or (iii) a mixture of two or more salts of a diastereomer or of a mixture of two or more diastereomers of the compound of formula (I), a diastereomer, salt or a mixture as defined above as a drug for topical application and/or for the treatment of lipoatrophy; the non-therapeutic use of a diastereomer, salt or a mixture as defined above for the prevention, treatment or reduction of skin aging, especially skin wrinkles; the use of a diastereomer, salt or a mixture as defined above for the production of an orally administered non-pharmaceutical preparation.

  本发明涉及包含(i)化合物的对映异构体或两个或两个以上对映异构体的混合物或(ii)化合物的对映异构体或两个或两个以上对映异构体的混合物的盐或(iii)化合物的对映异构体或两个或两个以上对映异构体的混合物的两个或两个以上盐的混合物的化妆品和药用制剂，上述对映异构体、盐或混合物被定义为用于局部应用的药物和/或治疗脂肪萎缩；上述对映异构体、盐或混合物的非治疗用途被定义为用于预防、治疗或减少皮肤老化，特别是皱纹；上述对映异构体、盐或混合物被定义为用于制造口服非药用制剂。
• Schistosomicidal and trypanocidal structure–activity relationships for (±)-licarin A and its (−)- and (+)-enantiomers
  作者：A.C. Pereira、L.G. Magalhães、U.O. Gonçalves、P.P. Luz、A.C.G. Moraes、V. Rodrigues、P.M. da Matta Guedes、A.A. da Silva Filho、W.R. Cunha、J.K. Bastos、N.P.D. Nanayakkara、M.L.A. e Silva

  DOI：10.1016/j.phytochem.2011.04.007

  日期：2011.8

  (+/-)-Licarin A (1) was obtained by oxidative coupling, and its enantiomers, (-)-licarin A (2) and (+)-licarin A (3), were resolved by chiral HPLC. Schistosomicidal and trypanocidal activities of these compounds were evaluated in vitro against Schistosoma mansoni adult worms and trypomastigote forms of Trypanosoma cruzi. The racemic mixture (1) displayed significant schistosomicidal activity with an LC50 value of 53.57 mu M and moderate trypanocidal activity with an IC50 value of 127.17 mu M. On the other hand, the (-)-enantiomer (2), displaying a LC50 value of 91.71 mu M, was more active against S. mansoni than the (+)-enantiomer (3), which did not show activity. For the trypanocidal assay, enantiomer 2 showed more significant activity (IC50 of 23.46 mu M) than enantiomer 3, which showed an IC50 value of 87.73 mu M. Therefore, these results suggest that (+/-)-licarin A (1) and (-)-licarin A (2) are promising compounds that could be used for the development of schistosomicidal and trypanocidal agents. (C) 2011 Elsevier Ltd. All rights reserved.

  (±)- Licensing A (1) 通过氧化偶联获得，其对映体 (-)-licarin A (2) 和 (+)-licarin A (3) 通过手性 HPLC 分离得到。这些化合物在体外对曼氏血吸虫成虫和克氏锥虫的锥鞭毛体形式进行了抗血吸虫和抗锥虫活性评估。外消旋混合物 (1) 显示出显著的抗血吸虫活性，LC50 值为 53.57 μM，并具有中等抗锥虫活性，IC50 值为 127.17 μM。另一方面，(-)-对映体 (2) 显示出 LC50 值为 91.71 μM，对 S. mansoni 的作用比 (+)-对映体 (3) 更有效，而 (3) 未显示活性。在抗锥虫实验中，对映体 2 显示出比对映体 3 更显著的活性，其 IC50 值分别为 23.46 μM 和 87.73 μM。因此，这些结果表明 (±)-licarin A (1) 和 (-)-licarin A (2) 是有前途的化合物，可用于开发抗血吸虫和抗锥虫剂。© 2011 Elsevier Ltd. 保留所有权利。