(2R,3S,4R,5S)-tetrahydro-2,5-bis-(4-hydroxy-3-methoxyphenyl)-3,4-furandimethanol | 129387-93-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: (2R,3S,4R,5S)-tetrahydro-2,5-bis-(4-hydroxy-3-methoxyphenyl)-3,4-furandimethanol
• 英文别名: rel-(7R,8S,7'S,8'R)-4,9,4',9'-tetrahydroxy-3,3'-dimethoxy-7,7'-epoxylignan
• CAS: 129387-93-5
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: NYDZRKZVFLLTLO-GOFCXKROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108.61
• 氢给体数：
  4.0
• 氢受体数：
  7.0

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 作用下， 反应 6.0h， 生成 (2R,3S,4R,5S)-tetrahydro-2,5-bis-(4-hydroxy-3-methoxyphenyl)-3,4-furandimethanol
  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

• Four New Lignan Glycosides from Osmanthus fragransLour. var. aurantiacusMakino
  作者：Koichi Machida、Megumi Yamauchi、Eriko Kurashina、Masao Kikuchi

  DOI：10.1002/hlca.201000074

  日期：2010.11

  Four new tetrahydrofuranoid lignan glycosides, (7S,8R,7′R,8′S)‐4,9,4′,7′‐tetrahydroxy‐3,3′‐dimethoxy‐7,9′‐epoxylignan 9‐O‐β‐D‐glucopyranoside (2), (7R,8S,7′S,8′R)‐4,9,4′,7′‐tetrahydroxy‐3,3′‐dimethoxy‐7,9′‐epoxylignan 9‐O‐β‐D‐glucopyranoside (3), (7R,8S,7′R,8′S)‐4,9,4′,9′‐tetrahydroxy‐3,3′‐dimethoxy‐7,7′‐epoxylignan 9‐O‐β‐D‐glucopyranoside (4), and rel‐(7R,8S,7′S,8′R)‐4,9,4′,9′‐tetrahydroxy‐3,3′‐dimethoxy‐7

  四个新木脂素tetrahydrofuranoid苷，（7小号，8 - [R，7' - [R，8'小号）-4,9,4'，7'-四羟基-3,3'-二甲氧基- 7,9'-epoxylignan 9- ö - β - d吡喃葡萄糖苷（2），（7 - [R，8小号，7'小号，8' - [R）-4,9,4'，7'-四羟基-3,3'-二甲氧基- 7,9'- epoxylignan 9- ø - β - d吡喃葡萄糖苷（3），（7 - [R，8小号，7' - [R，8'小号）-4,9,4'，9'-四羟基-3,3'-二甲氧基- 7 ，7'-环氧木脂素9-ø - β - d吡喃葡萄糖苷（4），和rel-（7 - [R，8小号，7'小号，8' - [R）-4,9,4'，9'-四羟基-3,3'-二甲氧基- 7 ，7'- epoxylignan 9- ø - β - d吡喃葡萄糖苷（5），和10木脂素甙，已知1和6
• Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity
  作者：Hisashi Nishiwaki、Kumiko Nakayama、Yoshihiro Shuto、Satoshi Yamauchi

  DOI：10.1021/jf4046396

  日期：2014.1.22

  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.