epitrachelogenin

• 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: epitrachelogenin
• 英文别名: (3R,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: YFVZKLQNMNKWSB-YCRPNKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  α-<(tert-Butyldimethylsilyl)oxy>-α-(3,4-dimethoxyphenyl)acetonitrile 在 palladium on activated charcoal MoO5*pyridine*HMPA 、 potassium hexamethyldisilazane 、 二乙基异丙基胺 、 硫酸 、 四丁基氟化铵 、 氢气 、 L-Selectride 、 sodium hydride 、 溶剂黄146 、 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， 生成 epitrachelogenin
  参考文献：
  名称：

  α-取代的顺式-α，β-二苄基-γ-丁内酯的高度立体选择性合成

  摘要：

  α-替补顺-α，β二苄基γ丁内酯（1）中以良好的收率合成以高度非对映方式经由亲电加成反应到β，γ二取代的α苄基γ丁内酯的烯醇化物的金属（2）作为关键步骤。

  DOI：

  10.1016/s0040-4039(00)73562-3

文献信息

• A highly stereoselective synthesis of α-substituted cis-α, β-dibenzyl-γ-butyrolactones
  作者：Yasunori Moritani、Chiaki Fukushima、Tsuyoshi Ogiku、Tatsuzo Ukita、Toshikazu Miyagishima、Tameo Iwasaki

  DOI：10.1016/s0040-4039(00)73562-3

  日期：1993.4

  α-Substituted cis-α, β-dibenzyl-γ-butyrolactones (1) were synthesized in good yields in a highly diastereoselective manner via electrophilic additions to the metal enolates of β, γ-disubstituted α-benzyl-γ-butyrolactones (2) as a key step.

  α-替补顺-α，β二苄基γ丁内酯（1）中以良好的收率合成以高度非对映方式经由亲电加成反应到β，γ二取代的α苄基γ丁内酯的烯醇化物的金属（2）作为关键步骤。
• Lignanes. 16. Premières synthèses totales du (+)-wikstromol, de la (−)-trachélogénine, de la (−)-nortrachélogénine et des lignoïdes apparentés
  作者：Melle Kenza Khamlach、Robert Dhal、Eric Brown

  DOI：10.1016/s0040-4020(01)89041-4

  日期：——

  Racemic and optically active alpha,beta-dibenzyl-gamma-butyrolactones (of synthetic origin) were hydroxylated in the alpha position with respect to the carbonyl group, using oxygen in the presence of LHDS. This led to (-)-trachelogenin 1, (-)-nortrachelogenin 2 and (+)-wikstromol 3, whose interesting pharmacological properties were recently described. These natural lignans were correlated to (+/-)-methyltrachelogenin 12 whose relative structure was definitely established by X-ray cristallography.
• 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.