(E)-1-(2-benzyloxy-6-hydroxy-4-methoxymethoxyphenyl)-3-(4-benzyloxy-3-methoxyphenyl)propenone | 1429227-33-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(2-benzyloxy-6-hydroxy-4-methoxymethoxyphenyl)-3-(4-benzyloxy-3-methoxyphenyl)propenone
• 英文别名: (E)-1-[2-hydroxy-4-(methoxymethoxy)-6-phenylmethoxyphenyl]-3-(3-methoxy-4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 1429227-33-7
• 化学式: C₃₂H₃₀O₇
• 分子量: 526.586
• InChiKey: SFBJRFBTQAGHQP-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-1-(2-benzyloxy-6-hydroxy-4-methoxymethoxyphenyl)-3-(4-benzyloxy-3-methoxyphenyl)propenone 在 咪唑 、 sodium tetrahydroborate 、 甲基磺酰胺 、 cerium(III) chloride heptahydrate 、 AD-mix-α 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 163.0h， 生成 (2R,3S)-5-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-7-(methoxymethoxy)chroman-3-yl propionate
  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：

  1-[2-羟基-4,6-双(甲氧基甲氧基)苯基]乙酮,2',4'-双(甲氧基甲氧基)-6'-羟基苯乙酮 在 水 、 sodium hydride 、 potassium carbonate 作用下， 以 正庚烷 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 23.67h， 生成 (E)-1-(2-benzyloxy-6-hydroxy-4-methoxymethoxyphenyl)-3-(4-benzyloxy-3-methoxyphenyl)propenone
  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

• 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.