(3R^*,4R^*)-3-methyl-3-<3,4-(methylenedioxy)benzyl>-4-(3,4-dimethoxybenzyl)-γ-butyrolactone | 131318-40-6

• 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^*,4R^*)-3-methyl-3-<3,4-(methylenedioxy)benzyl>-4-(3,4-dimethoxybenzyl)-γ-butyrolactone
• CAS: 131318-40-6；131318-41-7
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: BZFHRVZJYBRYLT-ZHRRBRCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  4-[(3,4-二甲氧基苯基)甲基]二氢呋喃-2-酮 在 双(三甲基硅烷基)氨基钾 、 lithium diisopropyl amide 作用下， 反应 5.83h， 生成 (3R^*,4R^*)-3-methyl-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

• A synthesis of α-substituted trans-α, β-dibenzyl-γ-butyrolactones: diastereofacial differentiation in the electrophilic attack on the metal enolates of α, β-dibenzyl-γ-butyrolactones
  作者：Moritani Yasunori、Ukita Tatsuzo、Nishitani Takashi、Seki Masahiko、Iwasaki Tameo

  DOI：10.1016/s0040-4039(00)94458-7

  日期：1990.1

  α-Substituted trans-α, β-dibenzyl-γ-butyrolactones were synthesized in a diastereoselective manner by the reaction of the potassium enolates of α, β-dibenzyl-γbutyrolactones with electrophiles. The method was applied to the synthesis of (±)trachelogenin.

  通过α ，β-二苄基-γ-丁内酯的烯醇钾与亲电子试剂的反应，以非对映选择性的方式合成α-取代的反式-α，β-二苄基-γ-丁内酯。该方法应用于（±）trachelogenin的合成。