α-(3,4-dimethoxyphenyl)-6-bromoveratryl alcohol | 149143-83-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-(3,4-dimethoxyphenyl)-6-bromoveratryl alcohol
• CAS: 149143-83-9
• 化学式: C₁₇H₁₉BrO₅
• 分子量: 383.239
• InChiKey: LNAHWTATLVYZCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  α-(3,4-dimethoxyphenyl)-6-bromoveratryl alcohol 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 、 sodium t-butanolate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 、 甲苯 、 叔丁醇 、 苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 113.12h， 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：

  4-溴黎芦醚 、 6-溴藜芦醛 在 正丁基锂 作用下， 生成 α-(3,4-dimethoxyphenyl)-6-bromoveratryl alcohol
  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.