(E)-ethyl 6-<2-(3-benzyloxy-4-methoxyphenyl)ethenyl>-2-hydroxybenzoate | 172484-36-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-ethyl 6-<2-(3-benzyloxy-4-methoxyphenyl)ethenyl>-2-hydroxybenzoate
• 英文别名: ethyl 6-<2-(3-benzyloxy-4-methoxyphenyl)ethenyl>salicylate；ethyl 6-[2-(3-benzyloxy-4-methoxyphenyl)ethenyl]salicylate；ethyl 2-hydroxy-6-[(E)-2-(4-methoxy-3-phenylmethoxyphenyl)ethenyl]benzoate
• CAS: 172484-36-5
• 化学式: C₂₅H₂₄O₅
• 分子量: 404.463
• InChiKey: ZQOAKHJDZVCOJM-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 6-<2-(3-benzyloxy-4-methoxyphenyl)ethenyl>-2-hydroxybenzoate 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 23.55h， 生成 (-)-phyllodulcin
  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 、 3-苄氧基-4-甲氧基苯甲醛 在 sodium ethanolate 作用下， 生成 (E)-ethyl 6-<2-(3-benzyloxy-4-methoxyphenyl)ethenyl>-2-hydroxybenzoate
  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

• Synthesis of Dihydroisocoumarins, (±)-Hydrangenol and (±)-Phyllodulcin, Utilizing an Annelation Reaction of Enaminones with Ethyl Acetoacetate. Studies on the b-Carbonyl Componuds Connected with the b-Polyketides XIII
  作者：Naoki Takeuchi、Takako Nakano、Kaori Goto、Seisho Tobinaga

  DOI：10.3987/com-92-s16

  日期：——

  Naturally occurring dihydroisocoumarins, (+/-) -hydrangenol (1) and (+/-) -phyllodulcin (2) were synthesized from the enaminones (3) and (4) by the annelation reactions with ethyl acetoacetate (5).
• 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.