(3R^*,4S^*)-3-deuterio-3-[3,4-(methylenedioxy)benzyl]-4-(3,4-dimethoxybenzyl)-γ-butyrolactone

• 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: (3R^*,4S^*)-3-deuterio-3-[3,4-(methylenedioxy)benzyl]-4-(3,4-dimethoxybenzyl)-γ-butyrolactone
• 化学式: C₂₁H₂₂O₆
• 分子量: 371.394
• InChiKey: LEVKKQBBEVGIKN-TTYLMGMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4-dimethoxyphenyl)acetonitrile 在 palladium on activated charcoal 硫酸 、 四丁基氟化铵 、 氢气 、 重水 、 双(三甲基硅烷基)氨基钾 、 L-Selectride 、 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， -78.0~40.0 ℃ 、354.64 kPa 条件下， 反应 74.0h， 生成 (3R^*,4S^*)-3-deuterio-3-[3,4-(methylenedioxy)benzyl]-4-(3,4-dimethoxybenzyl)-γ-butyrolactone
  参考文献：
  名称：

  Stereoselective Syntheses of Cis- and Trans-Isomers of α-Hydroxy-α,β-dibenzyl-γ-butyrolactone Lignans:  New Syntheses of (±)-Trachelogenin and (±)-Guayadequiol

  摘要：

  Cis- and trans-isomers of alpha-hydroxy-alpha,beta-dibenzyI-gamma-butyrolactone lignans 1a,d-g and 2a,c,d were stereoselectively synthesized in good yields based on the electrophilic addition to the metal enolate of alpha-benzyl-gamma-butyolactone derivatives 1l-o and 3 as a key step, This method was applied to the syntheses of (+/-)-trachelogenin and (+/-)-guayadequiol, representative examples of the trans- and cis-isomers of alpha-hydroxy-alpha,beta-dibenzyl-y-butyrolactone lignan series.

  DOI：

  10.1021/jo9601932

文献信息

• Stereoselective Syntheses of <i>Cis</i>- and <i>Trans</i>-Isomers of α-Hydroxy-α,β-dibenzyl-γ-butyrolactone Lignans:  New Syntheses of (±)-Trachelogenin and (±)-Guayadequiol
  作者：Yasunori Moritani、Chiaki Fukushima、Tatsuzo Ukita、Toshikazu Miyagishima、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1021/jo9601932

  日期：1996.1.1

  Cis- and trans-isomers of alpha-hydroxy-alpha,beta-dibenzyI-gamma-butyrolactone lignans 1a,d-g and 2a,c,d were stereoselectively synthesized in good yields based on the electrophilic addition to the metal enolate of alpha-benzyl-gamma-butyolactone derivatives 1l-o and 3 as a key step, This method was applied to the syntheses of (+/-)-trachelogenin and (+/-)-guayadequiol, representative examples of the trans- and cis-isomers of alpha-hydroxy-alpha,beta-dibenzyl-y-butyrolactone lignan series.