(+)-picrodimethylretrodendrin | 150132-92-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: (+)-picrodimethylretrodendrin
• 英文别名: (3aS,4S,9aR)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one
• CAS: 150132-92-6
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: YNINSHKHTZESCP-SZFUDVHCSA-N

物化性质

• 沸点：
  552.1±50.0 °C(predicted)
• 密度：
  1.207±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-picrodimethylretrodendrin 在 sodium t-butanolate 作用下， 以 叔丁醇 为溶剂， 反应 24.0h， 以94%的产率得到(-)-(1S,2R,3R)-1-(3',4'-dimethoxyphenyl)-3-(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid lactone
  参考文献：
  名称：

  A general asymmetric synthesis of (-)-.alpha.-dimethylretrodendrin and its diastereomers

  摘要：

  A Diels-Alder cycloaddition between the fumarate of methyl (R)-mandelate 14 and alpha-hydroxy-alpha'-aryl-o-quinodimethane 12 produced an exo cycloadduct 15 in 44% yield which was converted to optically pure (-)-alpha-dimethylretrodendrin(21) and three of its diastersomers. The 1,2,3-cis diastersomer 19 was found to possess an unexpected conformation as deduced from NOE experiments.

  DOI：

  10.1021/jo00067a057
• 作为产物：
  描述：

  6-溴藜芦醛 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 二氧化硫 、 氢气 、 sodium methylate 、 三乙基硼氢化锂 、 对甲苯磺酸 、 三氟乙酸 、 zinc(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 106.2h， 生成 (+)-picrodimethylretrodendrin
  参考文献：
  名称：

  A general asymmetric synthesis of (-)-.alpha.-dimethylretrodendrin and its diastereomers

  摘要：

  A Diels-Alder cycloaddition between the fumarate of methyl (R)-mandelate 14 and alpha-hydroxy-alpha'-aryl-o-quinodimethane 12 produced an exo cycloadduct 15 in 44% yield which was converted to optically pure (-)-alpha-dimethylretrodendrin(21) and three of its diastersomers. The 1,2,3-cis diastersomer 19 was found to possess an unexpected conformation as deduced from NOE experiments.

  DOI：

  10.1021/jo00067a057

文献信息

• A general asymmetric synthesis of (-)-.alpha.-dimethylretrodendrin and its diastereomers
  作者：Shawn P. Maddaford、James L. Charlton

  DOI：10.1021/jo00067a057

  日期：1993.7

  A Diels-Alder cycloaddition between the fumarate of methyl (R)-mandelate 14 and alpha-hydroxy-alpha'-aryl-o-quinodimethane 12 produced an exo cycloadduct 15 in 44% yield which was converted to optically pure (-)-alpha-dimethylretrodendrin(21) and three of its diastersomers. The 1,2,3-cis diastersomer 19 was found to possess an unexpected conformation as deduced from NOE experiments.