(2S,3S)-2,3-Bis<(3,4-dimethoxyphenyl)hydroxymethyl>-1,4-butanediol | 72536-39-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 二苄基丁烷木脂素
• 英文名称: (2S,3S)-2,3-Bis<(3,4-dimethoxyphenyl)hydroxymethyl>-1,4-butanediol
• 英文别名: (2S,3S)-1,4-bis(3,4-dimethoxyphenyl)-2,3-bis(hydroxymethyl)butane-1,4-diol
• CAS: 72536-39-1
• 化学式: C₂₂H₃₀O₈
• 分子量: 422.475
• InChiKey: LQRCAWLJBNWJNW-KILAXVPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-Bis<(3,4-dimethoxyphenyl)hydroxymethyl>-1,4-butanediol 在 三氟化硼乙醚 作用下， 以44%的产率得到桉脂素
  参考文献：
  名称：

  μ-薄荷基氧丁烯内酯的不对称1,4-加成。（第三部分）1个对映体的（-）eudesmin合成。

  摘要：

  基于3,4-二甲氧基苯甲醛的芳基二硫醚的对映选择性迈克尔加成，将光学纯的（-）Eudesmin合成为（5S）-甲氧基-s [5H]-呋喃酮，总产率为16％。

  DOI：

  10.1016/s0040-4039(00)79733-4
• 作为产物：
  描述：

  (2R,3R)-3-(3,4-dimethoxybenzoyl)-1-(3,4-dimethoxyphenyl)-2-[(4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidine-1-carbonyl]-4-[(4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidin-1-yl]butane-1,4-dione 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-2,3-Bis<(3,4-dimethoxyphenyl)hydroxymethyl>-1,4-butanediol
  参考文献：
  名称：

  Stereoselective homocoupling of chiral 1-aroylacetyl-2-imidazolidinones by oxidation with Br2

  摘要：

  The oxidative coupling of sodium enolates of (4R,5S)-1-aroylacetyl-3,4-dimethyl-5-phenyl-2-imidazolidinones with Br-2 as the oxidant affords the R,R-dimers stereoselectively. The R,R-selectivity can be explained by a radical Coupling mechanism. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00488-3

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.
• Stereoselective intramolecular coupling of diaroylacetates of (1R,1′R)-exo,exo′-3,3′-biisoborneol by oxidation with Br2
  作者：Naoki Kise、Azumi Fujimoto、Noriaki Moriyama、Nasuo Ueda

  DOI：10.1016/s0957-4166(03)00572-x

  日期：2003.9

  The oxidative coupling of diaroylacetate derivatives prepared from (1R, 1'R)-exo,exo'-3,3'-biisoborneol with NaH-Br-2 gave the corresponding intramolecularly coupled products stereoselectively. The major (R,R)-isomers thus obtained were transformed to (-)-Sesamin and (-)-Eudesmin. (C) 2003 Elsevier Ltd. All rights reserved.