2-hydroxy-3,4,6-trimethoxybenzaldehyde | 65162-31-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-3,4,6-trimethoxybenzaldehyde
• CAS: 65162-31-4
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: LRGJWCQSWJHJKW-UHFFFAOYSA-N

物化性质

• 熔点：
  102-102.7 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  359.5±37.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3,4,6-trimethoxybenzaldehyde 在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 (2S,5S)-(-)-2-叔丁基-3-甲基-5-苯基-4-咪唑啉酮 作用下， 以 乙醚 、 甲苯 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  脂族醛向2-羟基查耳酮的高度对映选择性加成通过协同有机催化剂实现。

  摘要：

  在这里，我们开发了脂族醛对2-羟基查尔酮的对映选择性加成反应，而2-羟基查耳酮则通过协同有机催化剂促进，从而以优异的对映选择性获得杂合类黄酮。该反应利用2-羟基查耳酮的环异构化在24 W CFL的照射下形成瞬时黄酮，其被原位产生的手性烯胺中间体捕获。通过与瞬时黄酮进行离子配对，手性磷酸的协同作用确保了该反应的出色结果。

  DOI：

  10.1039/d0cc04424e
• 作为产物：
  描述：

  2,6-二甲氧基对苯二酚 在 氢氧化钾 、 三氯化硼 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 2-hydroxy-3,4,6-trimethoxybenzaldehyde
  参考文献：
  名称：

  Iinuma, Munekazu; Iwashima, Kiyoshi; Tanaka, Toshiyuki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 10, p. 4217 - 4219

  摘要：

  DOI：

文献信息

• Flavonoids synthesis. I. Synthesis and spectroscopic properties of flavones with two hydroxy and five methoxy groups at C-2',3',4',5,6,6',7 and C-2',3,4',5,5',6,7.
  作者：MUNEKAZU IINUMA、YOSHINOBU MATOBA、TOSHIYUKI TANAKA、MIZUO MIZUNO

  DOI：10.1248/cpb.34.1656

  日期：——

  Four flavones oxygenated at C-2', 3', 4' and 6', and seven flavonols oxygenated at C-2', 4' and 5', each with a 5, 6, 7-trioxygenated structure in ring A, were synthesized for comparison with brickellin and apulein. The structures of brickelin and apulein were thus confirmed to be 2', 5-dihydroxy-3, 4', 5', 6, 7-pentamethoxyflavone and 2', 5'-dihydroxy-3, 4', 5, 6, 7-pentamethoxyflavone, respectively. The differences between flavones oxygenated at 2', 3', 4' and 6', and flavonols oxygenated at C-2', 4', 5' are discussed on the basis of spectroscopic data.

  合成了四种2'、3'、4'、6'位羟基化的黄酮及七种2'、4'、5'位羟基化的黄酮醇，它们均在A环的5、6、7位上羟基化，与brickellin和apulein进行对比，确认了brickellin和apulein的结构分别为2'，5'-二羟基-3'，4'，5'，6'，7-五甲氧基黄酮及2'，5-二羟基-3'，4'，5，6，7-五甲氧基黄酮。根据波谱数据讨论了2'、3'、4'、6'位羟基化的黄酮及C-2'、4'、5'位羟基化的黄酮醇之间的区别。
• Total synthesis of naturally occurring 5,6,7- and 5,7,8-trioxygenated coumarins
  作者：Dominick Maes、Maria Eugenia Riveiro、Carina Shayo、Carlos Davio、Silvia Debenedetti、Norbert De Kimpe

  DOI：10.1016/j.tet.2008.02.059

  日期：2008.5

  The synthesis of five naturally occurring polyoxygenated coumarins is described. It concerns two 5,6,7-trioxygenated coumarins, i.e., 6-hydroxy-5,7-dimethoxycoumarin (fraxinol) 1 and 5,6,7-trimethoxycoumarin 2, and three 5,7,8-trioxygenated coumarins, i.e., 8-hydroxy-5,7-dimethoxycoumarin (leptodactylone) 3, 5,7,8-trimethoxycoumarin 4 and 8-(3-methyl-2-butenyloxy)-5,7-dimethoxycoumarin (artanin) 5

  描述了五种天然存在的多加氧香豆素的合成。它涉及两个5,6,7-三加氧香豆素，即6-羟基-5,7-二甲氧基香豆素（fraxinol）1和5,6,7-三甲氧基香豆素2，以及三个5,7,8-三加氧的香豆素，即8-羟基-5,7-二甲氧基（leptodactylone）3，5,7,8- trimethoxycoumarin 4和8-（3-甲基-2-丁烯氧基）-5,7-二甲氧基（artanin）5。合成途径的关键特征是合成合适的四氧化苯甲醛，然后通过维蒂希反应将其转化为相应的香豆素。
• Reaction of 2,3,4,6-tetramethoxybenzaldehyde with aluminum chloride. Selective cleavage at position 2 and selective ether exchange at position 3
  作者：Edward G. Paul、Paul Sun-Chi Wang

  DOI：10.1021/jo01327a066

  日期：1979.6
• Toward establishing structure–activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells
  作者：María E. Riveiro、Dominick Maes、Ramiro Vázquez、Monica Vermeulen、Sven Mangelinckx、Jan Jacobs、Silvia Debenedetti、Carina Shayo、Norbert De Kimpe、Carlos Davio

  DOI：10.1016/j.bmc.2009.08.002

  日期：2009.9

  The presumption that some coumarins might be lead compounds in the search for new differentiation agents against leukemia is based on the fact that natural coumarins, 5-(3-methyl-2-butenyloxy)-6,7-methylenedioxycoumarin (C-2) and 5-methoxy-6,7-methylenedioxycoumarin (C-1) inhibit proliferation and induce differentiation in U-937 cells [Riveiro, M. E.; Shayo, C.; Monczor, F.; Fernandez, N.; Baldi, A.; De Kimpe, N.; Rossi, J.; Debenedetti, S.; Davio, C. Cancer Lett. 2004, 210, 179-188]. These promising findings prompted us to investigate the anti-leukemia activity of a broader range of related polyoxygenated coumarins. Twenty related natural or synthetically prepared coumarins, including a range of 5-substituted ayapin derivatives which have become easy accessible via newly developed synthesis methods, were evaluated, where treatments with 5-(2,3-dihydroxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-3) and 5-(2-hydroxy-3-methoxy-3-methylbutoxy)-6,7-methylenedioxycoumarin (D-2) were able to inhibit the cell growth and induce the differentiation of U-937 cells after 48 h treatment. These results provide insight into the correlation between some structural properties of polyoxygenated coumarins and their in vitro leukemic differentiation activity. (C) 2009 Elsevier Ltd. All rights reserved.
• PAUL E. G.; WANG P. S., J. ORG. CHEM., 1979, 44, NO 13, 2307-2308
  作者：PAUL E. G.、 WANG P. S.

  DOI：——

  日期：——