(8R,8'S)-3,3'-methoxy-9,9'-epoxylignane-4,4'-diol

• 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: (8R,8'S)-3,3'-methoxy-9,9'-epoxylignane-4,4'-diol
• 英文别名: (-)-trans-3,4-divanilyltetrahydrofuran；meso-shonanin；shonanin；meso-divanillyltetrahydrofuran；4-[[(3R,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-3-yl]methyl]-2-methoxyphenol
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: ROGUIJKVZZROIQ-IYBDPMFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  6
• 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

• 作为反应物：
  描述：

  (E)-4-methoxymethyl-3-methoxycinnamic acid 、 (8R,8'S)-3,3'-methoxy-9,9'-epoxylignane-4,4'-diol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 C₃₂H₃₆O₉
  参考文献：
  名称：

  （±）-二香草基四氢呋喃阿魏酸酯的全合成

  摘要：

  描述了一种合成芝麻基苏木和苏式-（±）-二香草基四氢呋喃阿魏酸酯的简便方法。合成基于统一的合成策略，该策略涉及两次Stobbe缩合以生成木脂素的骨架，然后进行还原反应以形成内消旋和苏-异（±）-异二十二碳五烯醇。内消旋-和苏式- （±）-secoisolanciresinol通过快速柱色谱法分离，通过用分子内的TsCl反应，得到关键中间体，随后内消旋-或苏-与阿魏酸（±）-shonanin，然后缩合以获得sesquilignan苏-或其类似物赤型-（±）-二香草基四氢呋喃阿魏酸酯。

  DOI：

  10.1007/s12039-010-0050-7
• 作为产物：
  描述：

  (3R,4S)-3-(4-benzyloxy-3-methoxybenzyl)-4-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]tetrahydrofuran 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以90%的产率得到(8R,8'S)-3,3'-methoxy-9,9'-epoxylignane-4,4'-diol
  参考文献：
  名称：

  First Discovery of Insecticidal Activity of 9,9′-Epoxylignane and Dihydroguaiaretic Acid against Houseflies and the Structure–Activity Relationship

  摘要：

  The insecticidal activity of (-)-(8R,8'R)-3,3'-dimethoxy-9,9'-epoxylignane-4,4'-diol (1) against houseflies was clarified for the first time. The activities of other stereoisomers were weaker than that of the (8R,8'R)-stereoisomer. In the course of research into structure activity relationships involving 30 newly synthesized (8R,8'R)-derivatives, 5-fold higher activity (ED50 = 0.91 nmol/fly) was observed for (-)-(8R,8'R)-3,3',4-trimethoicy-9,9'-epoxylignan-4'-ol (21) than for the naturally occurring compound (1). The activity of I was weaker than that of (-)-(8R,8'R)-dihydroguaiaretic acid ((-)-DGA) (4); however, compound 21 showed almost the same level of activity as 4.

  DOI：

  10.1021/jf400300n

文献信息

• An efficient method for the synthesis of lignans
  作者：Qian Wang、Yong Yang、Ying Li、Wei Yu、Zi Jie Hou

  DOI：10.1016/j.tet.2006.03.111

  日期：2006.6

  An efficient approach for the synthesis of several types of lignans (dibenzylbutanediols, dibenzylbutanes, substituted tetrahydrofurans, aryldihydronaphthalenes, arylnaphthalenes, and aryltetralins) was developed. The regioselective oxidative coupling of ethyl ferulate was used as the key step.

  开发了一种有效的合成几种类型的木脂素的方法（二苄基丁二醇，二苄基丁烷，取代的四氢呋喃，芳基二氢萘，芳基萘和芳基四氢化萘）。阿魏酸乙酯的区域选择性氧化偶联被用作关键步骤。
• Total synthesis of (±)-divanillyltetrahydrofuran ferulate
  作者：Ya-Mu Xia、Jia You、Qi Wang

  DOI：10.1007/s12039-010-0050-7

  日期：2010.5

  A convenient method for the synthesis of sesquilignan threo- and erythro-(±)-divanillyltetrahydrofuran ferulate is described. The synthesis was based on a unified synthetic strategy involving two Stobbe condensations to give the skeleton of lignan, and then reduction reaction to form meso- and threo-(±)-secoisolanciresinol. meso- and threo-(±)-secoisolanciresinol were separated by flash column chromatography

  描述了一种合成芝麻基苏木和苏式-（±）-二香草基四氢呋喃阿魏酸酯的简便方法。合成基于统一的合成策略，该策略涉及两次Stobbe缩合以生成木脂素的骨架，然后进行还原反应以形成内消旋和苏-异（±）-异二十二碳五烯醇。内消旋-和苏式- （±）-secoisolanciresinol通过快速柱色谱法分离，通过用分子内的TsCl反应，得到关键中间体，随后内消旋-或苏-与阿魏酸（±）-shonanin，然后缩合以获得sesquilignan苏-或其类似物赤型-（±）-二香草基四氢呋喃阿魏酸酯。
• First Discovery of Insecticidal Activity of 9,9′-Epoxylignane and Dihydroguaiaretic Acid against Houseflies and the Structure–Activity Relationship
  作者：Tuti Wukirsari、Hisashi Nishiwaki、Ayaka Hasebe、Yoshihiro Shuto、Satoshi Yamauchi

  DOI：10.1021/jf400300n

  日期：2013.5.8

  The insecticidal activity of (-)-(8R,8'R)-3,3'-dimethoxy-9,9'-epoxylignane-4,4'-diol (1) against houseflies was clarified for the first time. The activities of other stereoisomers were weaker than that of the (8R,8'R)-stereoisomer. In the course of research into structure activity relationships involving 30 newly synthesized (8R,8'R)-derivatives, 5-fold higher activity (ED50 = 0.91 nmol/fly) was observed for (-)-(8R,8'R)-3,3',4-trimethoicy-9,9'-epoxylignan-4'-ol (21) than for the naturally occurring compound (1). The activity of I was weaker than that of (-)-(8R,8'R)-dihydroguaiaretic acid ((-)-DGA) (4); however, compound 21 showed almost the same level of activity as 4.