matairesinyl 4,4'-bistriflate | 501645-95-0

• 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: matairesinyl 4,4'-bistriflate
• 英文别名: [2-methoxy-4-[[(3R,4R)-4-[[3-methoxy-4-(trifluoromethylsulfonyloxy)phenyl]methyl]-5-oxooxolan-3-yl]methyl]phenyl] trifluoromethanesulfonate
• CAS: 501645-95-0
• 化学式: C₂₂H₂₀F₆O₁₀S₂
• 分子量: 622.517
• InChiKey: XIPIOLVDJVMOOW-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  matairesinyl 4,4'-bistriflate 在 bis-triphenylphosphine-palladium(II) chloride lithium aluminium tetrahydride 、 甲酸 、 1,3-双(二苯基膦)丙烷 、 三溴化硼 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 肠二醇
  参考文献：
  名称：

  Synthesis of (−)-Matairesinol, (−)-Enterolactone, and (−)-Enterodiol from the Natural Lignan Hydroxymatairesinol

  摘要：

  [GRAPHICS]We describe here a four-step semisynthetic method for the preparation of enantiomerically pure (-)-enterolactone starting from the readily available lignan hydroxymatairesinol from Norway spruce (Picea abies). Hydroxymatairesinol was first hydrogenated to matairesinol. Matairesinol was esterified to afford the matairesinyl 4,4'-bistriflate, which was deoxygenated by palladium-catalyzed reduction to 3,3'-dimethylenterolactone. Demethylation of 3,3'-dimethylenterolactone and reduction with LiAlH4 yielded (-)-enterolactone and (-)-enterodiol, respectively.

  DOI：

  10.1021/ol0273598
• 作为产物：
  描述：

  hydroxymatairesinol 在 palladium on activated charcoal lutidine 、 氢气 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 50.0 ℃ 、800.01 kPa 条件下， 反应 52.0h， 生成 matairesinyl 4,4'-bistriflate
  参考文献：
  名称：

  Synthesis of (−)-Matairesinol, (−)-Enterolactone, and (−)-Enterodiol from the Natural Lignan Hydroxymatairesinol

  摘要：

  [GRAPHICS]We describe here a four-step semisynthetic method for the preparation of enantiomerically pure (-)-enterolactone starting from the readily available lignan hydroxymatairesinol from Norway spruce (Picea abies). Hydroxymatairesinol was first hydrogenated to matairesinol. Matairesinol was esterified to afford the matairesinyl 4,4'-bistriflate, which was deoxygenated by palladium-catalyzed reduction to 3,3'-dimethylenterolactone. Demethylation of 3,3'-dimethylenterolactone and reduction with LiAlH4 yielded (-)-enterolactone and (-)-enterodiol, respectively.

  DOI：

  10.1021/ol0273598

文献信息

• Synthesis of (−)-Matairesinol, (−)-Enterolactone, and (−)-Enterodiol from the Natural Lignan Hydroxymatairesinol
  作者：Patrik Eklund、Anna Lindholm、J.-P. Mikkola、Annika Smeds、Reko Lehtilä、Rainer Sjöholm

  DOI：10.1021/ol0273598

  日期：2003.2.1

  [GRAPHICS]We describe here a four-step semisynthetic method for the preparation of enantiomerically pure (-)-enterolactone starting from the readily available lignan hydroxymatairesinol from Norway spruce (Picea abies). Hydroxymatairesinol was first hydrogenated to matairesinol. Matairesinol was esterified to afford the matairesinyl 4,4'-bistriflate, which was deoxygenated by palladium-catalyzed reduction to 3,3'-dimethylenterolactone. Demethylation of 3,3'-dimethylenterolactone and reduction with LiAlH4 yielded (-)-enterolactone and (-)-enterodiol, respectively.