4-benzyloxy-2,3,6-trimethoxybenzaldehyde | 52249-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzyloxy-2,3,6-trimethoxybenzaldehyde
• 英文别名: 4-Benzyl-2,3,6-trimethoxybenzaldehyd；4-(Benzyloxy)-2,3,6-trimethoxybenzaldehyde；2,3,6-trimethoxy-4-phenylmethoxybenzaldehyde
• CAS: 52249-82-8
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: QINQKJIIDLROSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  475.2±40.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-2,3,6-trimethoxybenzaldehyde 在 氢氧化钾 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 7.0h， 生成 4'-benzyloxy-2',3',5,6,6',7-hexamethoxyflavone
  参考文献：
  名称：

  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.

  摘要：

  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。

  DOI：

  10.1248/cpb.34.1656
• 作为产物：
  描述：

  5-溴香兰素 在 铜 、 sodium carbonate 、 potassium carbonate 、 间氯过氧苯甲酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 22.5h， 生成 4-benzyloxy-2,3,6-trimethoxybenzaldehyde
  参考文献：
  名称：

  A concise synthesis of viscolin, and its anti-inflammatory effects through the suppression of iNOS, COX-2, ERK phosphorylation and proinflammatory cytokines expressions

  摘要：

  In the present report, a concise synthesis of viscolin (1) has been achieved. The anti-inflammatory effect of viscolin was investigated in vitro and in vivo. Viscolin blocked the expression of iNOS and COX-2, and it also inhibited the ERIC for the activation of NF-kappa B in LPS-stimulated RAW 264.7 macrophages. Western blotting and immunohistochemical analysis revealed that viscolin decreased Carr-induced iNOS and COX-2 expressions. These results could help to deduce the anti-inflammatory mechanisms. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.008

文献信息

• Total synthesis and biological evaluation of viscolin, a 1,3-diphenylpropane as a novel potent anti-inflammatory agent
  作者：Chung-Ren Su、Yuh-Chiang Shen、Ping-Chung Kuo、Yann-Lii Leu、Amooru G. Damu、Yea-Hwey Wang、Tian-Shung Wu

  DOI：10.1016/j.bmcl.2006.09.046

  日期：2006.12

  Total synthesis of viscolin, an anti-inflammatory 1,3-diphenylpropane isolated from Viscum coloratum, employing the Wittig reaction is reported. Key steps in the synthesis of viscolin depend on the selection of protecting groups to maintain the para hydroxyl group that is the most critical chemical structure influencing the biological activity of viscolin and the utilization of microwave-assisted Wittig

  报道了使用Wittig反应的粘胶的全合成，粘胶是一种从发色豌豆（Viscum coloratum）分离的消炎的1，3-二苯基丙烷。粘胶蛋白合成的关键步骤取决于保护对羟基的保护基团的选择，该对羟基是影响粘胶蛋白生物学活性的最关键化学结构，并利用微波辅助的维蒂希（Wittig）烯化反应。评估了合成粘胶蛋白，其前体产物16及其类似物17的抗炎作用，这些作用是通过它们对白细胞和小胶质细胞中活性氧（ROS），一氧化氮（NO）以及促炎性细胞因子产生的影响来进行的。
• A concise synthesis of viscolin, and its anti-inflammatory effects through the suppression of iNOS, COX-2, ERK phosphorylation and proinflammatory cytokines expressions
  作者：Guan-Jhong Huang、M. Vijaya Bhaskar Reddy、Ping-Chung Kuo、Chieh-Hung Huang、Hung-Cheng Shih、E.-Jian Lee、Mei-Lin Yang、Yann-Lii Leu、Tian-Shung Wu

  DOI：10.1016/j.ejmech.2011.12.008

  日期：2012.2

  In the present report, a concise synthesis of viscolin (1) has been achieved. The anti-inflammatory effect of viscolin was investigated in vitro and in vivo. Viscolin blocked the expression of iNOS and COX-2, and it also inhibited the ERIC for the activation of NF-kappa B in LPS-stimulated RAW 264.7 macrophages. Western blotting and immunohistochemical analysis revealed that viscolin decreased Carr-induced iNOS and COX-2 expressions. These results could help to deduce the anti-inflammatory mechanisms. (C) 2011 Elsevier Masson SAS. All rights reserved.
• 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。