(2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide | 868127-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide
• CAS: 868127-84-8
• 化学式: C₄₃H₅₄O₈Si
• 分子量: 726.982
• InChiKey: RLMAJZIFGJRQPD-CDEFLAKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.62
• 重原子数：
  52.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide 在 palladium on activated charcoal 4 A molecular sieve 、 四丁基氟化铵 、 氢气 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 19.0h， 生成 (2S,3R)-2,3-bis(4-hydroxy-3-methoxybenzoyl)-4-butanolide
  参考文献：
  名称：

  Radical and Superoxide Scavenging Activities of Matairesinol and Oxidized Matairesinol

  摘要：

  研究了氧化马黛茶酚的自由基和超氧化物清除活性。可以推断，游离苄基位置对更高的自由基清除活性非常重要。7′-oxomatairesinol (Mat 2) 和 7-oxomatairesinol (Mat 3) 的活性水平不同。8-hydroxymatairesinol 的活性低于 matairesinol（Mat 1）。氧化马黛茶酚的超氧化物清除活性也是首次得到证实。据推测，氧化的马黛茶酚中苯酚的 pKa 值影响了这种活性。

  DOI：

  10.1271/bbb.60096
• 作为产物：
  描述：

  (3R)-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide 、 4-苄氧基-3-甲氧基苯甲醛 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以81%的产率得到(2S,3R)-2-[(S)-(4-benzyloxy-3-methoxyphenyl)(hydroxy)methyl]-3-[(R)-(4-benzyloxy-3-methoxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide
  参考文献：
  名称：

  Effect of Benzylic Oxygen on the Antioxidant Activity of Phenolic Lignans

  摘要：

  It has been clarified in the present investigation that a high degree of oxidation at the benzylic position of phenolic lignans bearing a 4-hydroxy-3-methoxybenzyl group reduces their antioxidant activity and that the antioxidant activity of the bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran lignan 2 is higher than that of the corresponding gamma-butyrolactone lignan 1. This was demonstrated by comparing the antioxidant activities of compounds 1 and 2 with those of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4, the bis(hydroxybenzyl)tetrahydrofurans 7 and 8, the (benzoyl)(benzyl)tetrahydrofuran 6, and the dibenzoyltetrahydrofuran 9. The activity level of compound 2 was approximately the same potency as that of the tetrahydronaphthalene-tetrahydrofuran 5. These compounds possess either a 4-hydroxy3-methoxybenzyl group or a 4-hydroxy-3-methoxybenzoyl group as the benzyl or benzoyl group. An examination of radical scavenging activity showed differences of activity between diastereomers. To make this comparison possible, compounds 1-9 were synthesized using new synthetic routes for several of these lignans. In this investigation, stereoisomers of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4 and liovils 7 and 8 were synthesized for the first time.

  DOI：

  10.1021/np050089s

文献信息

• Effect of the Benzylic Structure of Lignan on Antioxidant Activity
  作者：Satoshi YAMAUCHI、Takuya SUGAHARA、Junko MATSUGI、Tatsushi SOMEYA、Toshiya MASUDA、Taro KISHIDA、Koichi AKIYAMA、Masafumi MARUYAMA

  DOI：10.1271/bbb.70275

  日期：2007.9.23

  The effect of the benzylic structure of lignan on antioxidant activity was evaluated. Secoisolariciresinol (1) and 3,4-bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran (2), which have two secondary benzylic positions without oxygen, showed the highest antioxidant activity. Optically active verrucosin (4) was synthesized for the first time in this experiment.

  评估了木酚类化合物苄基结构对抗氧化活性的影响。没有氧的两个二级苄位的次羟基瑞士素 (1) 和3,4-双(4-羟基-3-甲氧基苄基)四氢呋喃 (2) 显示出最高的抗氧化活性。本实验中首次合成了具有光学活性的疣酮 (4)。