(3R,4R,5R)-4-<1,3-Benzodioxol-5-ylbis(phenylthio)methyl>-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone | 158665-03-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (3R,4R,5R)-4-<1,3-Benzodioxol-5-ylbis(phenylthio)methyl>-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone
• 英文别名: (3R,4R,5R)-4-[1,3-benzodioxol-5-yl-bis(phenylsulfanyl)methyl]-3-[(3-methoxy-4-phenylmethoxyphenyl)methyl]-5-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxolan-2-one
• CAS: 158665-03-3
• 化学式: C₄₉H₅₂O₇S₂
• 分子量: 817.08
• InChiKey: PVHMGDKLRFGITJ-IFIUSBFESA-N

物化性质

• 沸点：
  880.0±65.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  58
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R,4R,5R)-4-<1,3-Benzodioxol-5-ylbis(phenylthio)methyl>-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone 在 palladium on activated charcoal 氢氧化钾 、 sodium tetrahydroborate 、 氢气 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 22.0h， 生成 (3R,4R)-4-(1,3-苯并二氧戊环-5-基甲基)二氢-3-[(4-羟基-3-甲氧基苯基)甲基]-2(3H)-呋喃酮
  参考文献：
  名称：

  Enantioselective Synthesis of Natural Dibenzylbutyrolactone Lignans (-)-Enterolactone, (-)-Hinokinin, (-)-Pluviatolide, (-)-Enterodiol, and Furofuran Lignan (-)-Eudesmin via Tandem Conjugate Addition to .gamma.-Alkoxybutenolides

  摘要：

  A general and efficient method is described for the asymmetric synthesis of a variety of lignans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)-eudesmin (30) in 16% overall yield from 5b are described.

  DOI：

  10.1021/jo00099a033
• 作为产物：
  描述：

  4-苄氧基-3-甲氧基苯甲醇 在 正丁基锂 、 四甲基乙二胺 、 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 22.5h， 生成 (3R,4R,5R)-4-<1,3-Benzodioxol-5-ylbis(phenylthio)methyl>-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone
  参考文献：
  名称：

  Enantioselective Synthesis of Natural Dibenzylbutyrolactone Lignans (-)-Enterolactone, (-)-Hinokinin, (-)-Pluviatolide, (-)-Enterodiol, and Furofuran Lignan (-)-Eudesmin via Tandem Conjugate Addition to .gamma.-Alkoxybutenolides

  摘要：

  A general and efficient method is described for the asymmetric synthesis of a variety of lignans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)-eudesmin (30) in 16% overall yield from 5b are described.

  DOI：

  10.1021/jo00099a033

文献信息

• Enantioselective Synthesis of Natural Dibenzylbutyrolactone Lignans (-)-Enterolactone, (-)-Hinokinin, (-)-Pluviatolide, (-)-Enterodiol, and Furofuran Lignan (-)-Eudesmin via Tandem Conjugate Addition to .gamma.-Alkoxybutenolides
  作者：Arjan van Oeveren、Johan F. G. A. Jansen、Ben L. Feringa

  DOI：10.1021/jo00099a033

  日期：1994.10

  A general and efficient method is described for the asymmetric synthesis of a variety of lignans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)-eudesmin (30) in 16% overall yield from 5b are described.