2,4',4-trimethoxymethoxychalcone | 251909-34-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,4',4-trimethoxymethoxychalcone
• 英文别名: (E)-retro-2,4,4'-tri-O-methoxymethylchalcone；2,4,4'-tri-O-methoxymethyl-retro-chalcone；(E)-3-[2,4-bis(methoxymethoxy)phenyl]-1-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 251909-34-9
• 化学式: C₂₁H₂₄O₇
• 分子量: 388.417
• InChiKey: ROVMUUPKCDINAK-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,4',4-trimethoxymethoxychalcone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 以99%的产率得到1-(4'-O-methoxymethylphenyl)-3-(2'',4''-di-O-methoxymethylphenyl)-1-propanol
  参考文献：
  名称：

  Studies on Flavans. III. The Total Synthesis of (±)-7,4′-Dihydroxy-3′-methoxyflavan, (±)-7,3′-Dihydroxy-4′-methoxyflavan, and (±)-7,4′-Dihydroxyflavan

  摘要：

  The first total synthesis of (+/-)-7,3'-dihydroxy-4'-methoxyflavan (1) and (+/-)-7,4'-dihydroxy-3'-methoxyflavan (2), along with the synthesis of (+/-)-7,4'-dihydroxyflavan (3), three naturally occurring flavans, were described. The key step is the cyclization of 1,3-diaryl-1-propanol by (BF3Et2O)-Et-..

  DOI：

  10.1081/scc-120024733
• 作为产物：
  描述：

  苯(甲)醛,2,4-二(甲氧基甲氧基)- 、 1-[4-(甲氧基甲氧基)苯基]乙酮 在 氢氧化钾 作用下， 以72%的产率得到2,4',4-trimethoxymethoxychalcone
  参考文献：
  名称：

  The novel flavan-3-ol, (2R,3S)-guibourtinidol and its diastereomers

  摘要：

  The novel (2R,3S)-guibourtinidol, representing the first flavan-3-ol with 4',7-dihydroxy phenolic substitution pattern, was identified in the heartwood of Cassia abbreviata. Asymmetric dihydroxylation of (E)-1-(4'-O-methoxymethylphenyl)-3-(2 ",4 " di- O-methoxymethylphenyl)-propene with AD-mix-alpha or AD-mix-beta and subsequent acid-catalyzed cyclization afforded the four free phenolic guibourtinidol diastereomers, essentially enantiopure and in good yield. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00348-9

文献信息

• Nel, Reinier J. J.; Heerden, Pieter S. van; Rensburg, Hendrik van, Journal of Chemical Research, Miniprint, 1999, # 10, p. 2610 - 2625
  作者：Nel, Reinier J. J.、Heerden, Pieter S. van、Rensburg, Hendrik van、Ferreira, Daneel

  DOI：——

  日期：——
• The novel flavan-3-ol, (2R,3S)-guibourtinidol and its diastereomers
  作者：Reinier J.J Nel、Makhosazana Mthembu、Johan Coetzee、Hendrik van Rensburg、Elfranco Malan、Daneel Ferreira

  DOI：10.1016/s0031-9422(99)00348-9

  日期：1999.11

  The novel (2R,3S)-guibourtinidol, representing the first flavan-3-ol with 4',7-dihydroxy phenolic substitution pattern, was identified in the heartwood of Cassia abbreviata. Asymmetric dihydroxylation of (E)-1-(4'-O-methoxymethylphenyl)-3-(2 ",4 " di- O-methoxymethylphenyl)-propene with AD-mix-alpha or AD-mix-beta and subsequent acid-catalyzed cyclization afforded the four free phenolic guibourtinidol diastereomers, essentially enantiopure and in good yield. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Studies on Flavans. III. The Total Synthesis of (±)-7,4′-Dihydroxy-3′-methoxyflavan, (±)-7,3′-Dihydroxy-4′-methoxyflavan, and (±)-7,4′-Dihydroxyflavan
  作者：Jijun Xue、Xianshu Zhang、Xuesong Chen、Yingpeng Zhang、Ying Li

  DOI：10.1081/scc-120024733

  日期：2003.10

  The first total synthesis of (+/-)-7,3'-dihydroxy-4'-methoxyflavan (1) and (+/-)-7,4'-dihydroxy-3'-methoxyflavan (2), along with the synthesis of (+/-)-7,4'-dihydroxyflavan (3), three naturally occurring flavans, were described. The key step is the cyclization of 1,3-diaryl-1-propanol by (BF3Et2O)-Et-..