2,4-bis(benzyloxy)-6-hydroxybenzaldehyde | 863237-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-bis(benzyloxy)-6-hydroxybenzaldehyde
• 英文别名: 2,4-Bis(benzyloxy)-6-hydroxybenzaldehyde；2-hydroxy-4,6-bis(phenylmethoxy)benzaldehyde
• CAS: 863237-56-3
• 化学式: C₂₁H₁₈O₄
• 分子量: 334.372
• InChiKey: VOVATTFSGDLECM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-bis(benzyloxy)-6-hydroxybenzaldehyde 在 氢氧化钾 、 sodium tetrahydroborate 、 溴 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三苯基膦 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 (E)-(5-(3-(2,4-bis(benzyloxy)-6-(methoxymethoxy)-phenyl)prop-1-enyl)-1,3-phenylene)bis(oxy)bis(methylene)-dibenzene
  参考文献：
  名称：

  Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus

  摘要：

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.086
• 作为产物：
  描述：

  间苯三酚甲醛 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60 %的产率得到2,4-bis(benzyloxy)-6-hydroxybenzaldehyde
  参考文献：
  名称：

  C7 修饰的红糖苷类似物的合成

  摘要：

  通过在 C5 处选择性氯化核心结构，然后在 C7 处进行 Duff 甲酰化，制备了在 C7 处具有不同酰基的桃金娘酮的各种类似物。在保护酚羟基后，一系列格氏反应、氧化和脱保护得到类似物。事实证明，其中一些人非常活跃。

  DOI：

  10.1002/ejoc.202300259

文献信息

• Total synthesis of mangiferin, homomangiferin, and neomangiferin
  作者：Xiong Wei、Danlin Liang、Qing Wang、Xiangbao Meng、Zhongjun Li

  DOI：10.1039/c6ob01622g

  日期：——

  Total synthesis of mangiferin, homomangiferin, and neomangiferin, three C-glycosyl xanthone natural products with a wide spectrum of pharmacological effects, has been achieved starting from 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranose. The key steps involve a stereoselective Lewis acid promoted C-glycosylation of protected phloroglucinol with tetrabenzylglucopyranosyl acetate and a highly regioselective

  从2,3,4,6-四-O-苄基-α/β- D-起始已实现了芒果苷，高芒果苷和新芒果苷的全合成，这是三种具有广泛药理作用的C-糖基yl吨酮天然产物。吡喃葡萄糖。关键步骤包括用四苄基吡喃葡萄糖基乙酸酯立体选择性的路易斯酸促进受保护的间苯三酚的C-糖基化和高度区域选择性的碱基诱导的环化，以构建核心黄酮骨架。
• An expedient synthesis of enantioenriched substituted (2-benzofuryl)arylcarbinols via tandem Rap–Stoermer and asymmetric transfer hydrogenation reactions
  作者：Gullapalli Kumaraswamy、Gajula Ramakrishna、Ragam Raju、Mogilisetti Padmaja

  DOI：10.1016/j.tet.2010.10.074

  日期：2010.12

  An expedient synthesis of enantioenriched substituted (benzofuran-yl)-aryl and heteroaryl carbinols, is described. A key feature of this protocol is synthesis of functionally varied benzofuran scaffolds via a Rap–Stoermer reaction/catalytic asymmetric transfer hydrogenation (ATH) using substituted salicylaldehyde and α-haloaryl, heteroaryl ketones.

  描述了方便合成富含对映体的取代的（苯并呋喃基）-芳基和杂芳基甲醇。该协议的关键特征是使用取代的水杨醛和α-卤代芳基，杂芳基酮通过Rap-Stoermer反应/催化不对称转移氢化（ATH）合成功能多样的苯并呋喃骨架。
• Total Synthesis of Kehokorins A–E, Cytotoxic <i>p</i>-Terphenyls
  作者：Shunya Takahashi、Yasuaki Suda、Takemichi Nakamura、Koji Matsuoka、Hiroyuki Koshino

  DOI：10.1021/acs.joc.7b00147

  日期：2017.3.17

  This paper describes a general method for the synthesis of kehokorins A–E, novel cytotoxic p-terphenyls. 2,4,6-Trihydroxybenzaldehyde served as a common building block for preparation of the central aromatic ring. Construction of their p-terphenyl skeletons was achieved by a stepwise Suzuki–Miyaura coupling, whereas the phenyldibenzofuran moiety was built up by an intramolecular Ullmann reaction. Introduction

  本文介绍了一种合成kehokorins A–E，新型细胞毒性对-三联苯的通用方法。2,4,6-三羟基苯甲醛是制备中心芳香环的常用结构单元。通过逐步的Suzuki-Miyaura偶联可实现其对叔丁基骨架的构建，而苯基二苯并呋喃部分则通过分子内乌尔曼反应建立。通过三氯乙亚氨酸酯方法将1-鼠李糖残基引入到部分保护的酮可可林B中。
• Asymmetric total synthesis of B-ring modified (−)-epicatechin gallate analogues and their modulation of β-lactam resistance in Staphylococcus aureus
  作者：James C. Anderson、Catherine Headley、Paul D. Stapleton、Peter W. Taylor

  DOI：10.1016/j.tet.2005.05.086

  日期：2005.8

  Two enantiomerically pure B-ring modified analogues of (-)epicatechin gallate were synthesised and their modulation of beta-lactam resistance using three strains of methicillin resistant Staphylococcus aureus (BB 568, EMRSA-15 and EMRSA-16) evaluated. Sub-inhibitory concentrations (12.5 and 25 mg/L) of the two analogues fully sensitised each of the three MRSA strains to oxacillin, reducing the MIC to less than 0.5 mg/L, identical to levels achieved with ECg. Lower concentrations demonstrated that the position and degree of hydroxylation of the B-ring is important for activity. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of Rhodomyrtone Analogs Modified at C7
  作者：Marvin Wenninger、Martin E. Maier、Aparna Viswanathan Ammanath、Li Huang、Friedrich Götz

  DOI：10.1002/ejoc.202300259

  日期：2023.6

  Various analogs of rhodomyrtone with different acyl groups at C7 were prepared by selective chlorination of the core structure at C5 followed by a Duff formylation at C7. After protection of the phenolic OH groups, a sequence of Grignard reaction, oxidation, and deprotection led to the analogs. Some of them turned out to be very active.

  通过在 C5 处选择性氯化核心结构，然后在 C7 处进行 Duff 甲酰化，制备了在 C7 处具有不同酰基的桃金娘酮的各种类似物。在保护酚羟基后，一系列格氏反应、氧化和脱保护得到类似物。事实证明，其中一些人非常活跃。