bis[(1R)-2-methoxy-2-oxo-1-phenylethyl] (1S,2S,3R,4S)-1-(3,4-dimethoxyphenyl)-4-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate | 149143-84-0

• 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: bis[(1R)-2-methoxy-2-oxo-1-phenylethyl] (1S,2S,3R,4S)-1-(3,4-dimethoxyphenyl)-4-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate
• CAS: 149143-84-0
• 化学式: C₄₀H₄₀O₁₃
• 分子量: 728.75
• InChiKey: VBXKBONBNUVSQQ-UWNKZCSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  13

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3-carbomethoxy-6,7-dimethoxy-1-(1,2-cis)-(3',4'-dimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-(2,3-cis)-2-carboxylic acid	149143-86-2	C23H26O8	430.455
  ——	(-)-(1S,2R,3R)-1-(3',4'-dimethoxyphenyl)-3-(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid lactone	4718-24-5	C22H24O6	384.429
  ——	(+)-picrodimethylretrodendrin	150132-92-6	C22H24O6	384.429
  ——	(-)-isopicrodimethylretrodendrin	——	C22H24O6	384.429
  ——	(+)-isodimethylretrodendrin	150132-93-7	C22H24O6	384.429
  ——	(1S,2S,3S)-1-(3,4-Dimethoxy-phenyl)-3-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid	149143-88-4	C22H26O7	402.444
  ——	(1S,2S)-1-(3,4-Dimethoxy-phenyl)-6,7-dimethoxy-1,2-dihydro-naphthalene-2,3-dicarboxylic acid 3-methyl ester	149143-85-1	C23H24O8	428.439

反应信息

• 作为反应物：
  描述：

  bis[(1R)-2-methoxy-2-oxo-1-phenylethyl] (1S,2S,3R,4S)-1-(3,4-dimethoxyphenyl)-4-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate 在 palladium on activated charcoal 氢气 、 sodium methylate 、 三乙基硼氢化锂 、 对甲苯磺酸 、 sodium t-butanolate 作用下， 以 甲醇 、 溶剂黄146 、 乙酸乙酯 、 叔丁醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 105.0h， 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 、 三氟乙酸 、 zinc(II) oxide 作用下， 以 二氯甲烷 、 溶剂黄146 、 甲苯 、 苯 为溶剂， 反应 25.2h， 生成 bis[(1R)-2-methoxy-2-oxo-1-phenylethyl] (1S,2S,3R,4S)-1-(3,4-dimethoxyphenyl)-4-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate
  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.