4-benzyloxy-6-hydroxy-2-(methoxymethoxy)acetophenone | 1365537-25-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-benzyloxy-6-hydroxy-2-(methoxymethoxy)acetophenone
• 英文别名: 1-[2-Hydroxy-6-(methoxymethoxy)-4-phenylmethoxyphenyl]ethanone；1-[2-hydroxy-6-(methoxymethoxy)-4-phenylmethoxyphenyl]ethanone
• CAS: 1365537-25-2
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: GHAQSZQTBCOFMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-6-hydroxy-2-(methoxymethoxy)acetophenone 在 奎宁环 、 sodium tetrahydroborate 、 甲基磺酰胺 、 cerium(III) chloride heptahydrate 、 osmium tri chloride trihydrate 、 sodium hydride 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醇 、 正庚烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 、 叔丁醇 为溶剂， 反应 87.67h， 生成
  参考文献：
  名称：

  Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates

  摘要：

  Ten orthogonally protected (-)-epicatechin and 3'- or 4'-O-methyl-(-)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (-)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (-)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (-)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (-)-epicatechin glucuronides and sulfates. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.012
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 咪唑 、 四丁基氟化铵 、 potassium carbonate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 4-benzyloxy-6-hydroxy-2-(methoxymethoxy)acetophenone
  参考文献：
  名称：

  Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates

  摘要：

  Ten orthogonally protected (-)-epicatechin and 3'- or 4'-O-methyl-(-)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (-)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (-)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (-)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (-)-epicatechin glucuronides and sulfates. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.02.012

文献信息

• A versatile approach to the regioselective synthesis of diverse (−)-epicatechin-β-d-glucuronides
  作者：Eric S. Mull、Michael Van Zandt、Adam Golebiowski、R. Paul Beckett、Pradeep K. Sharma、Hagen Schroeter

  DOI：10.1016/j.tetlet.2012.01.054

  日期：2012.3

  A versatile new approach is reported for the total synthesis of five glucuronide metabolites of epicatechin, using selective protection/deprotection techniques. (C) 2012 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of orthogonally protected (2R,3R)-(−)-epicatechin derivatives, key intermediates in the de novo chemical synthesis of (−)-epicatechin glucuronides and sulfates
  作者：Mingbao Zhang、G. Erik Jagdmann、Michael Van Zandt、Paul Beckett、Hagen Schroeter

  DOI：10.1016/j.tetasy.2013.02.012

  日期：2013.4

  Ten orthogonally protected (-)-epicatechin and 3'- or 4'-O-methyl-(-)-epicatechin derivatives were prepared in a regiospecific and enantioselective manner. For each orthogonally protected (-)-epicatechin derivative, one specific phenolic hydroxyl was protected with a methoxymethyl (MOM) or p-methoxybenyzl (PMB) group and the remainder were protected as benzyl ethers. These uniquely protected (-)-epicatechin derivatives were designed to facilitate the regiospecific installation of a glucuronic acid or sulfate unit onto (-)-epicatechin after selective removal of the MOM or PMB protecting group to provide authentic standards of (-)-epicatechin glucuronides and sulfates. (c) 2013 Elsevier Ltd. All rights reserved.