(-)-(1S,2R,3R)-1-(3',4'-dimethoxyphenyl)-3-(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid lactone | 4718-24-5

• 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: (-)-(1S,2R,3R)-1-(3',4'-dimethoxyphenyl)-3-(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid lactone
• 英文别名: α-retrodendrin dimethyl ether；(-)-α-dimethylretrodendrin；Di-O-methyl-α-retrodendrin；Dimethyl-α-retrodendrin；(3aR,4S,9aR)-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one
• CAS: 4718-24-5
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: YNINSHKHTZESCP-WVFSVQOHSA-N

物化性质

• 熔点：
  181.5-189.5 °C(Solv: methanol (67-56-1); chloroform (67-66-3)(4:1))
• 沸点：
  552.1±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(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：

  (-)-(1S,2R,3R)-1-(3',4'-dimethoxyphenyl)-3-(hydroxymethyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid lactone 在 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 生成 dehydrodimethylretrodendrin
  参考文献：
  名称：

  Conidendrin. II.¹ The Stereochemistry and Reactions of the Lactone Ring²

  摘要：

  DOI：

  10.1021/ja01649a021
• 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 、 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 130.2h， 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

文献信息

• (R)-(+)-β-Veratryl-γ-butyrolactone. A new key-intermediate for the asymmetric synthesis of various lignans
  作者：Eric Brown、Alain Daugan

  DOI：10.1016/s0040-4039(00)83862-9

  日期：1986.1

  α-veratrylhemisuccinate was resolved into its (R)-(+) and (S)-(−) antipodes by (S)-(−) and (R)-(+)-α-methylbenzylamine respectively. Calcium borohydride reduction of the (R)-(+)-hemiester afforded (R)-(+)-β-veratryl-γ-butyrolactone. The latter was used for the synthesis of various naturlly occurring lignans such as (+)-dimethylisolariciresinol, (−)-kusunokinin and (−)-dimethylmatairesinol.

  α-藜芦基琥珀酸甲酯分别通过（S）-（-）和（R）-（+）-α-甲基苄基胺分解为（R）-（+）和（S）-（-）对映体。（R）-（+）-半胱氨酸的硼氢化钙还原得到（R）-（+）-β-藜芦基-γ-丁内酯。后者被用于合成各种天然存在的木脂素，例如（+）-二甲基异拉西里醇，（-）-苦参素和（-）-二甲基马来甾醇。
• Pelter, Andrew; Ward, Robert S.; Jones, D. Martin, Journal of the Chemical Society. Perkin transactions I, 1993, # 21, p. 2621 - 2630
  作者：Pelter, Andrew、Ward, Robert S.、Jones, D. Martin、Maddocks, Peter

  DOI：——

  日期：——
• Application of Tosylate Reductions and Molecular Rotations to the Stereochemistry of Lignans²
  作者：Anthony W. Schrecker、Jonathan L. Hartwell

  DOI：10.1021/ja01607a063

  日期：1955.1
• 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.
• Conidendrin. II.¹ The Stereochemistry and Reactions of the Lactone Ring²
  作者：Merle E. Cisney、Wilbur L. Shilling、W. M. Hearon、David W. Goheen

  DOI：10.1021/ja01649a021

  日期：1954.10