3-(4'-苄氧基苯基)-8-羟基-3,4-二氢-2-苯并吡喃-1-酮 | 637774-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 3-(4'-苄氧基苯基)-8-羟基-3,4-二氢-2-苯并吡喃-1-酮
• 英文名称: 3-(4'-benzyloxyphenyl)-8-hydroxy-3,4-dihydro-2-benzopyran-1-one
• 英文别名: 8-Hydroxy-3-(4-phenylmethoxyphenyl)-3,4-dihydroisochromen-1-one
• CAS: 637774-32-4
• 化学式: C₂₂H₁₈O₄
• 分子量: 346.383
• InChiKey: GRFZGAYIUKESRX-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C
• 沸点：
  579.4±50.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4'-苄氧基苯基)-8-羟基-3,4-二氢-2-苯并吡喃-1-酮 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以84%的产率得到绣球酚
  参考文献：
  名称：

  Efficient syntheses of (±)-hydrangenol, (±)-phyllodulcin and (±)-macrophyllol

  摘要：

  In this paper we report on a efficient and flexible synthetic route towards the total syntheses of the dihydrocoumarine derivatives hydrangenol (1), phyllodulcin (1a) and macrophyllol (6b). The syntheses started with a readily available phosphonium salt 2 and suitable modified benzaldehydes 3/3a/3b resulting in 46 to 61% overall yields in three to four-steps sequences. The racemic products could be separated by chiral HPLC. The evidence of the(R)-enantiomer for sweetness could be demonstrated for la. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.046
• 作为产物：
  描述：

  (3-acetyloxy-2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide 在 氢氧化钾 、 sodium ethanolate 、 三氟乙酸 作用下， 以 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 53.0h， 生成 3-(4'-苄氧基苯基)-8-羟基-3,4-二氢-2-苯并吡喃-1-酮
  参考文献：
  名称：

  Efficient syntheses of (±)-hydrangenol, (±)-phyllodulcin and (±)-macrophyllol

  摘要：

  In this paper we report on a efficient and flexible synthetic route towards the total syntheses of the dihydrocoumarine derivatives hydrangenol (1), phyllodulcin (1a) and macrophyllol (6b). The syntheses started with a readily available phosphonium salt 2 and suitable modified benzaldehydes 3/3a/3b resulting in 46 to 61% overall yields in three to four-steps sequences. The racemic products could be separated by chiral HPLC. The evidence of the(R)-enantiomer for sweetness could be demonstrated for la. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.09.046

文献信息

• Efficient syntheses of (±)-hydrangenol, (±)-phyllodulcin and (±)-macrophyllol
  作者：Mehmet Günes、Andreas Speicher

  DOI：10.1016/j.tet.2003.09.046

  日期：2003.10

  In this paper we report on a efficient and flexible synthetic route towards the total syntheses of the dihydrocoumarine derivatives hydrangenol (1), phyllodulcin (1a) and macrophyllol (6b). The syntheses started with a readily available phosphonium salt 2 and suitable modified benzaldehydes 3/3a/3b resulting in 46 to 61% overall yields in three to four-steps sequences. The racemic products could be separated by chiral HPLC. The evidence of the(R)-enantiomer for sweetness could be demonstrated for la. (C) 2003 Elsevier Ltd. All rights reserved.