4,4'-(3,4-dimethyltetrahydrofuran-2,5-diyl)bis(2-methoxyphenol) | 131829-51-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: 4,4'-(3,4-dimethyltetrahydrofuran-2,5-diyl)bis(2-methoxyphenol)
• 英文别名: tetrahydrofuroguaiacin B；isonectandrin B；nectandrin B；tetrahydrofurogualacin；Tetrahydro-furoguaiacin-B；4-[(2S,3R,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
• CAS: 131829-51-1
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: GMXMKSFJQLFOSO-SRRICDNISA-N

物化性质

• 沸点：
  509.7±50.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (7R,7′S,8S,8′R)-4,4′-dibenzyloxy-3,3′-dimethoxy-7,7′-epoxylignane-9,9′-diol 在 5%-palladium/activated carbon 、 氢气 、 三乙基硼氢化锂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 4,4'-(3,4-dimethyltetrahydrofuran-2,5-diyl)bis(2-methoxyphenol)
  参考文献：
  名称：

  Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity

  摘要：

  All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.

  DOI：

  10.1021/jf4046396

文献信息

• Structure-activity relationships of talaumidin derivatives: Their neurite-outgrowth promotion in vitro and optic nerve regeneration in vivo
  作者：Kenichi Harada、Katsuyoshi Zaha、Rina Bando、Ryo Irimaziri、Miwa Kubo、Yoshiki Koriyama、Yoshiyasu Fukuyama

  DOI：10.1016/j.ejmech.2018.02.014

  日期：2018.3

  talaumidin (1). However, the preparation of optically active (–)-2 requires a complicated synthetic route. To explore new neurotrophic compounds that can be obtained on a large scale, we established a short step synthetic route for talaumidin derivatives and synthesized fourteen analogues based on the structure of (–)-2. First, we synthesized a racemic compound of (–)-2 (2a) and assessed its neurotrophic

  （–）-Talaumidin（1），一种2,5-联芳基-3,4-二甲基四氢呋喃木脂素，显示出有效的神经营养活性，例如神经突增生和神经保护作用。以前，我们发现（–）-（1 S，2 R，3 S，4 R）-立体异构体2的活性比天然产物他洛米定（1）更为显着。但是，旋光性（–）- 2的制备需要复杂的合成路线。为了探索可以大规模获得的新的神经营养化合物，我们建立了talaumidin衍生物的短步合成路线，并基于（–）- 2的结构合成了十四种类似物。首先，我们合成了（–）- 2（2a）的外消旋化合物，并评估了其神经营养活性。我们发现外消旋体2a的神经营养特性与（–）- 2相似。使用相同的合成方法，合成了几种talaumidin衍生物，以优化芳环上的氧官能度。结果，双（亚甲基二氧基苯）衍生物2b具有最高的神经营养活性。此外，对2b的构效关系的研究表明，2,5-二苯基-四氢呋喃结构是必不可少的结构，THF
• POLYCYCLIC COMPOUNDS AND METHODS RELATED THERETO
  申请人：Chavez Kathryn J.

  公开号：US20110275708A1

  公开（公告）日：2011-11-10

  The invention relates to a novel compound of formula I or pharmaceutically acceptable salts thereof as well as pharmaceutical, nutraceutical, and botanical drug compositions and therapeutic methods related thereto. In certain embodiments, the compounds are used for the treatment of abnormal cell growth, hyperproliferative disorders, and inflammatory diseases in mammals. In other embodiments, the invention encompasses methods to isolate and synthesize the compounds.
• US8563603B2
  申请人：——

  公开号：US8563603B2

  公开（公告）日：2013-10-22