2,4-bis-(benzyloxy)-5-methoxybenzaldehyde | 7298-50-2

• 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: 2,4-bis-(benzyloxy)-5-methoxybenzaldehyde
• 英文别名: 2,4-dibenzyloxy-5-methoxybenzaldehyde；2,4-Dibenzlyoxy-5-methoxy-benzaldehyd；2,4-Dibenzyloxy-5-methoxybenzaldehyd；Benzaldehyde, 5-methoxy-2,4-bis(phenylmethoxy)-；5-methoxy-2,4-bis(phenylmethoxy)benzaldehyde
• CAS: 7298-50-2
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: YLJLNUPDSCGJTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-bis-(benzyloxy)-5-methoxybenzaldehyde 在 盐酸 、 氢氧化钾 作用下， 以 吡啶 、 乙醇 为溶剂， 生成 Acetic acid 3,5-bis-benzyloxy-2-[(E)-3-(2,4-bis-benzyloxy-5-methoxy-phenyl)-acryloyl]-phenyl ester
  参考文献：
  名称：

  Facile synthesis of polyhydroxycoumaronochromones with quinones: synthesis of alkylpolyhydroxy- and alkoxycoumaronochromones from 2′-hydroxyisoflavones

  摘要：

  4 ' ,5,7-Trihydroxy- or 8-alkyl-4 ' .5,7-trihvclroxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2 ' -hydroxyisoflavones with o-chloranil under mild conditions. By contrast, alkoxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2 ' -hydroxyisoflavones with DDQ. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01234-5
• 作为产物：
  描述：

  5-benzyloxy-2-methoxyacetophenone 在 sodium hydroxide 、 potassium carbonate 、 间氯过氧苯甲酸 、 三氟乙酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,4-bis-(benzyloxy)-5-methoxybenzaldehyde
  参考文献：
  名称：

  Facile synthesis of polyhydroxycoumaronochromones with quinones: synthesis of alkylpolyhydroxy- and alkoxycoumaronochromones from 2′-hydroxyisoflavones

  摘要：

  4 ' ,5,7-Trihydroxy- or 8-alkyl-4 ' .5,7-trihvclroxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2 ' -hydroxyisoflavones with o-chloranil under mild conditions. By contrast, alkoxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2 ' -hydroxyisoflavones with DDQ. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01234-5

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。
• Synthesis of Lamellarin U and Lamellarin G Trimethyl Ether by Alkylation of a Deprotonated α-Aminonitrile
  作者：Johannes C. Liermann、Till Opatz

  DOI：10.1021/jo800467e

  日期：2008.6.1

  1,2,3,4-Tetrahydroisoquinoline-1-carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions

  1,2,3,4-四氢异喹啉-1-腈可以用作起始的一锅合成5,6-二氢吡咯并[2,1的材料一]异喹啉和1-苄基-3,4-二氢异喹啉。后面的化合物以短的反应顺序被转化为薄片蛋白G三甲醚和薄片蛋白U。这种方法允许引入用于酚羟基官能团的酸敏感保护基，该保护基在经典的Bischler-Napieralski反应的苛刻条件下会裂解。
• Utility of Polymer-Supported Reagents in the Total Synthesis of Lamellarins
  作者：Poonsakdi Ploypradith、Rachel Kirk Kagan、Somsak Ruchirawat

  DOI：10.1021/jo050388m

  日期：2005.6.1

  Four solid-supported reagents have been utilized in the multistep synthesis of lamellarins. The use of Amberlyst A-26 Br-3(-) and polymer bound pyridine hydrobromide perbromide (PVPHP) for keto alpha-bromination of the less studied ortho-substituted acetophenone derivatives selectively furnished the corresponding monobromination products (phenacyl bromide derivatives), which were used directly in condensation reactions with benzyldihydroisoquinoline mediated by Amberlyst A-26 NaCO3-. The 2H-pyrrole carbonates subsequently underwent intramolecular Friedel-Crafts transacylation followed by lactonization to provide the lamellarin skeleton. Alternatively, Amberlyst A-26 NaCO3- effectively served as base in condensation reaction of benzyldihydroisoquinoline with alpha-nitrocinnamate derivatives to provide the corresponding 2-ethoxycarbonyl pyrroles, which smoothly underwent O-debenzylation reaction followed by lactonization to furnish the lamellarin skeleton. The novel Amberlyst-15 mediated lactonization reactions effectively combined the otherwise two separate steps into a single transformation.
• Facile synthesis of polyhydroxycoumaronochromones with quinones: synthesis of alkylpolyhydroxy- and alkoxycoumaronochromones from 2′-hydroxyisoflavones
  作者：Masao Tsukayama、Akihiro Oda、Yasuhiko Kawamura、Masaki Nishiuchi、Kazuyo Yamashita

  DOI：10.1016/s0040-4039(01)01234-5

  日期：2001.8

  4 ' ,5,7-Trihydroxy- or 8-alkyl-4 ' .5,7-trihvclroxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2 ' -hydroxyisoflavones with o-chloranil under mild conditions. By contrast, alkoxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2 ' -hydroxyisoflavones with DDQ. (C) 2001 Elsevier Science Ltd. All rights reserved.