(1S,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-1,2-dihydro-naphthalene-2,3-dicarboxylic acid 3-methyl ester | 149143-85-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (1S,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-1,2-dihydro-naphthalene-2,3-dicarboxylic acid 3-methyl ester
• CAS: 149143-85-1
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: HTDXFBCDHCASOQ-LEWJYISDSA-N

物化性质

• 沸点：
  578.6±50.0 °C(predicted)
• 密度：
  1.269±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-1,2-dihydro-naphthalene-2,3-dicarboxylic acid 3-methyl ester 在 palladium on activated charcoal 氢气 、 三乙基硼氢化锂 、 对甲苯磺酸 、 sodium t-butanolate 作用下， 以 溶剂黄146 、 乙酸乙酯 、 叔丁醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 81.0h， 生成 (-)-(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 吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 二氧化硫 、 sodium methylate 、 三氟乙酸 、 zinc(II) oxide 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 、 苯 为溶剂， 反应 49.2h， 生成 (1S,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-1,2-dihydro-naphthalene-2,3-dicarboxylic acid 3-methyl ester
  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.