2,3-双(3,4-二甲氧基亚苄基)丁二酸 | 73119-35-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: 2,3-双(3,4-二甲氧基亚苄基)丁二酸
• 英文名称: 2,3-bis(3,4-dimethoxybenzylidene)butanedioic acid
• 英文别名: bis-(3,4-dimethoxybenzylidene)succinic；bis(3,4-dimethoxybenzylidene)succinic acid；E,E-bis(3,4-dimethoxybenzylidene)succinic acid；diveratrylidenesuccinic acid；Di-((E)-veratryliden)-bernsteinsaeure；di-((E)-veratrylidene)-succinic acid；(2E,3E)-2,3-bis[(3,4-dimethoxyphenyl)methylidene]butanedioic acid
• CAS: 73119-35-4
• 化学式: C₂₂H₂₂O₈
• 分子量: 414.412
• InChiKey: RDNZVLBCRYBJGP-KAVGSWPWSA-N

物化性质

• 沸点：
  617.0±55.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3-双(3,4-二甲氧基亚苄基)丁二酸 在 四氢呋喃 、 甲醇 、 sodium hydroxide 、 lithium aluminium tetrahydride 、 乙醚 、 镍 、 丙酮 、 氢化铝 作用下， 生成 1,1'-(2,3-二甲基-1,4-丁烷二基)二(3,4-二甲氧基苯)
  参考文献：
  名称：

  meso-Dihydroguaiaretic Acid and its Derivatives²

  摘要：

  DOI：

  10.1021/ja01571a054
• 作为产物：
  描述：

  在 盐酸 、 sodium hydroxide 作用下， 反应 12.0h， 以82%的产率得到2,3-双(3,4-二甲氧基亚苄基)丁二酸
  参考文献：
  名称：

  由内消旋酸酐不对称合成木脂素内酯

  摘要：

  给出了内消旋-2,3-二苄基丁二酸酐的合成。该化合物与（+）-α-甲基苄基胺的反应非对映选择性地进行，得到丁二酸单酰胺，其转化为对映体富集的顺式-2，3-二苄基丁内酯木脂素。

  DOI：

  10.1016/0040-4020(96)00761-2

文献信息

• Rotamers and isomers in the fulgide series. Part 1. Stereochemistry and conformational analysis of bis-(3,4-dimethoxybenzylidene)succinic anhydrides by X-ray crystallography and molecular mechanics
  作者：Jan C. A. Boeyens、Louis Denner、Guido W. Perold

  DOI：10.1039/p29880001749

  日期：——

  two forms, the Z,Z-isomer and the arylnaphthalene derivative. X-Ray structures of these crystalline forms are reported. The conformations of the other rotamers were simulated by molecular mechanics, using an empirical force-field based on the observed structure of the symmetrical E,E-rotamer, described here. The aromatic rings of the E,E-isomers are eclipsed and under severe strain, which inhibits free

  双-（3,4-二甲氧基亚苄基）琥珀酸酐的构象分析表明，除了Z，Z-异构体外，该二芳基富马特的E，E-异构体还以三种不同的相对自由地可相互转化的手性旋转异构体及其对映异构体的形式出现。的ë，ê异构体经历容易脱氢以形成arylnaphthalene衍生物。获得具有两种形式的对称的E，E-旋转异构体Z，Z-异构体和芳基萘衍生物的晶体。X报道了这些结晶形式的射线结构。其他旋转异构体的构型是通过分子力学模拟的，使用的是经验力场，该力场基于此处描述的对称E，E-旋转异构体的观察结构。E，E-异构体的芳环会黯然失色，并处于严重的应变之下，这会抑制自由旋转。堆积能量仅促进可能的E，E-旋转异构体之一的结晶，并且对甲氧基取代基的取向具有显著作用。
• New Synthetic Route to Butanolide Lignans by a Ruthenium Complex Catalyzed Hydrogenation of the Corresponding Stobbe's Fulgenic Acids
  作者：Massimo Bambagiotti-Alberti、Silvia A. Coran、Franco F. Vinvieri、Nadia Mulinacci、Giuseppe M. L. Pieraccini

  DOI：10.3987/com-88-4321

  日期：——
• Dicaffeoyltartaric Acid Analogues Inhibit Human Immunodeficiency Virus Type 1 (HIV-1) Integrase and HIV-1 Replication at Nontoxic Concentrations
  作者：Ryan A. Reinke、Peter J. King、Joseph G. Victoria、Brenda R. McDougall、Guoxiang Ma、Yingqun Mao、Manfred G. Reinecke、W. Edward Robinson

  DOI：10.1021/jm010359d

  日期：2002.8.1

  The human immunodeficiency virus type 1 (HIV-1) is a major health problem worldwide. In this study, 17 analogues of L-chicoric acid, a potent inhibitor of HIV integrase were studied. Of these analogues, five submicromolar inhibitors of integrase were discovered and 13 compounds with activity against integrase at less than 10 muM were identified. Six demonstrated greater than 10-fold selectivity for HIV replication over cellular toxicity. Ten analogues inhibited HIV replication at nontoxic concentrations. Alteration of the linkages between the two bis-catechol rings, including the use of amides, mixed amide esters, cholate, and alkyl bridges, was explored. Amides were as active as esters but were more toxic in tissue culture. Alkyl and cholate bridges were significantly less potent against HIV-1 integrase in vitro and were inactive against HIV-1 replication. Two amino acid derivates and one digalloylderivative of L-chicoric acid (L-CA) showed improved selectivity over L-CA against integration in cell culture. These data suggest that in addition to the bis-catechols and free carboxylic acid groups reported previously, polar linkages are important constituents for optimal activity against HIV-1 integrase and that new derivatives can be developed with increased specificity for integration over HIV entry in vivo.
• Boshoff, Philip R.; Perold, Guido W., Journal of Chemical Research, Miniprint, 1986, # 2, p. 735 - 745
  作者：Boshoff, Philip R.、Perold, Guido W.

  DOI：——

  日期：——
• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18