(3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one | 172484-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one
• 英文别名: [(3R)-3-(3-hydroxy-4-methoxyphenyl)-1-oxo-3,4-dihydroisochromen-8-yl] (1R,4S)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 172484-39-8
• 化学式: C₂₆H₂₆O₈
• 分子量: 466.488
• InChiKey: XZRLOLAYTLHPQP-BAEUJYSMSA-N

物化性质

• 沸点：
  684.5±55.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.05h， 以99%的产率得到白花前胡甲素
  参考文献：
  名称：

  Enantiodifferentiation in Taste Perception of the phyllodulcins

  摘要：

  Both enantiomers of phyllodulcin 1 have been prepared. Ester 2 was synthesized in a Wittig reaction from O-benzyl isovanillin. The corresponding stilbene carboxylic acid 3 could be cyclized with CF3CO2H to produce the 3'-benzyl ether 4 of (+/-)-phyllodulcin. Acylation with (1R,4S)-camphanoyl chloride gave first 5 and after hydrogenolysis of the benzyl ether group in 5 the diastereomeric esters 6. The diastereomerically pure 8-(1R,4S)-camphanoate (+)-6 of (R)-phyllodulcin could be isolated by repeated recrystallization. With (1S,4R)-camphanoyl chloride the enantiomeric 8-(1S,4R)-camphanoate (-)-6 of O-phyllodulcin could be prepared via ent-5 from a mixture of the diastereomeric esters ent-6. Ethanolysis of (+)-6 gave (R)-phyllodulcin [(+)-1] with 99% ee. The enantiomeric (S)-(-)-1 with 98% ee could be obtained from (-)-6. While (+)-1, the enantiomer occuring in fermented leaves of amacha, has an intense sweet taste, the enantiomer (-)-1 is completely tasteless.

  DOI：

  10.1016/0957-4166(95)00367-x
• 作为产物：
  描述：

  (3-acetyloxy-2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氢气 、 sodium ethanolate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 29.83h， 生成 (3R)-(+)-8-<(1R,4S)-camphanoyloxy>-3,4-dihydro-3-(3-hydroxy-4-methoxyphenyl)-1H-2-benzopyran-1-one
  参考文献：
  名称：

  Enantiodifferentiation in Taste Perception of the phyllodulcins

  摘要：

  Both enantiomers of phyllodulcin 1 have been prepared. Ester 2 was synthesized in a Wittig reaction from O-benzyl isovanillin. The corresponding stilbene carboxylic acid 3 could be cyclized with CF3CO2H to produce the 3'-benzyl ether 4 of (+/-)-phyllodulcin. Acylation with (1R,4S)-camphanoyl chloride gave first 5 and after hydrogenolysis of the benzyl ether group in 5 the diastereomeric esters 6. The diastereomerically pure 8-(1R,4S)-camphanoate (+)-6 of (R)-phyllodulcin could be isolated by repeated recrystallization. With (1S,4R)-camphanoyl chloride the enantiomeric 8-(1S,4R)-camphanoate (-)-6 of O-phyllodulcin could be prepared via ent-5 from a mixture of the diastereomeric esters ent-6. Ethanolysis of (+)-6 gave (R)-phyllodulcin [(+)-1] with 99% ee. The enantiomeric (S)-(-)-1 with 98% ee could be obtained from (-)-6. While (+)-1, the enantiomer occuring in fermented leaves of amacha, has an intense sweet taste, the enantiomer (-)-1 is completely tasteless.

  DOI：

  10.1016/0957-4166(95)00367-x

文献信息

• Enantiodifferentiation in Taste Perception of the phyllodulcins
  作者：Reinhard Zehnter、Hans Gerlach

  DOI：10.1016/0957-4166(95)00367-x

  日期：1995.11

  Both enantiomers of phyllodulcin 1 have been prepared. Ester 2 was synthesized in a Wittig reaction from O-benzyl isovanillin. The corresponding stilbene carboxylic acid 3 could be cyclized with CF3CO2H to produce the 3'-benzyl ether 4 of (+/-)-phyllodulcin. Acylation with (1R,4S)-camphanoyl chloride gave first 5 and after hydrogenolysis of the benzyl ether group in 5 the diastereomeric esters 6. The diastereomerically pure 8-(1R,4S)-camphanoate (+)-6 of (R)-phyllodulcin could be isolated by repeated recrystallization. With (1S,4R)-camphanoyl chloride the enantiomeric 8-(1S,4R)-camphanoate (-)-6 of O-phyllodulcin could be prepared via ent-5 from a mixture of the diastereomeric esters ent-6. Ethanolysis of (+)-6 gave (R)-phyllodulcin [(+)-1] with 99% ee. The enantiomeric (S)-(-)-1 with 98% ee could be obtained from (-)-6. While (+)-1, the enantiomer occuring in fermented leaves of amacha, has an intense sweet taste, the enantiomer (-)-1 is completely tasteless.