(3R,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(3-methoxy-4-phenylmethoxyphenyl)methyl]oxolan-2-one | 124887-01-0

• 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)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(3-methoxy-4-phenylmethoxyphenyl)methyl]oxolan-2-one
• CAS: 124887-01-0；124988-55-2；131351-74-1；131351-75-2
• 化学式: C₂₈H₃₀O₇
• 分子量: 478.542
• InChiKey: AGVYHXRDSVLBAW-RBISFHTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(3-methoxy-4-phenylmethoxyphenyl)methyl]oxolan-2-one 在 Pd-Pt 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 10.0h， 以100%的产率得到epitrachelogenin
  参考文献：
  名称：

  Lignanes。16.合成首字母总计为（+）-wikstromol，（-）-trachélogénine，（（-）-nortrachélogénine）和表观密码。

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)89041-4
• 作为产物：
  描述：

  4-[(3,4-二甲氧基苯基)甲基]二氢呋喃-2-酮 在 MoO5*pyridine*HMPA 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 lithium diisopropyl amide 作用下， 反应 1.5h， 生成 (3R,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(3-methoxy-4-phenylmethoxyphenyl)methyl]oxolan-2-one
  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。
• Total syntheses of (-)-trachelogenin, (-)-nortrachelogenin and (+)-wikstromol
  作者：Kenza Khamlach、Robert Dhal、Eric Brown

  DOI：10.1016/s0040-4039(00)99653-9

  日期：1989.1

  β-dibenzyl-γ-butyrolactones (lignans of synthetic origin), and were correlated to (±)-methyltrachelogenin 9 whose relative structure was definitely established by X-ray cristallography. (-)-Trachelogenin 1 and (-)-nortrachelogenin 12 thus have the (8S,8′S) absolute configuration, whereas (+)-nortrachelogenin 20 (or wikstromol) has the (8R,8′R) absolute configuration.

  通过相应的α，β-二苄基-γ-丁内酯（合成来源的木脂素）的α-羟基化获得标题化合物，并将其与（±）-甲基trachelogenin 9相关联，后者的相对结构通过X射线结晶成像法确定。因此，（-）-Trachelogenin 1和（-）-nortrachelogenin 12具有（8S，8'S）绝对构型，而（+）-nortrachelogenin 20（或wikstromol）具有（8R，8'R）绝对构型。
• KHAMLACH, KENZA;DHAL, ROBERT;BROWN, ERIC, TETRAHEDRON LETT., 30,(1989) N7, C. 2221-2224
  作者：KHAMLACH, KENZA、DHAL, ROBERT、BROWN, ERIC

  DOI：——

  日期：——
• 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.
• 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.