(+/-)-1-(4-benzyloxyphenyl)-3,4-dihydroxybutan-1-one | 470665-19-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-1-(4-benzyloxyphenyl)-3,4-dihydroxybutan-1-one
• 英文别名: (rac)-1-(4-(benzyloxy)phenyl)-3,4-dihydroxybutan-1-one；3,4-Dihydroxy-1-(4-phenylmethoxyphenyl)butan-1-one
• CAS: 470665-19-1
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: CCWPTYBBQJDWDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(4-benzyloxyphenyl)-3,4-dihydroxybutan-1-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以36%的产率得到4-(4-hydroxyphenyl)butane-1,2,4-triol
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Hydroxyalkyl- and Hydroxyacyl-phenols and Their Benzyl Ethers

  摘要：

  New phenolic compounds with hydrophilic side chains were prepared from 4-benzyloxybenzaldehyde and alkenyl magnesium bromides, followed by Sharpless dihydroxylation and hydrogenolytic removal of the benzyl group. The resulting compounds were tested in an agar diffusion assay against gram positive bacteria, gram negative bacteria, and against the fungi Candida glabrata and Aspergillus niger.

  DOI：

  10.1002/1521-4184(200203)335:2/3<94::aid-ardp94>3.0.co;2-w
• 作为产物：
  描述：

  4-苄氧基苯甲醛 在 α-AD mix {K4[Fe(CN)6], OsO4, Na2CO3, (DHQ)2-PHAL} 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 13.0h， 生成 (+/-)-1-(4-benzyloxyphenyl)-3,4-dihydroxybutan-1-one
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Hydroxyalkyl- and Hydroxyacyl-phenols and Their Benzyl Ethers

  摘要：

  New phenolic compounds with hydrophilic side chains were prepared from 4-benzyloxybenzaldehyde and alkenyl magnesium bromides, followed by Sharpless dihydroxylation and hydrogenolytic removal of the benzyl group. The resulting compounds were tested in an agar diffusion assay against gram positive bacteria, gram negative bacteria, and against the fungi Candida glabrata and Aspergillus niger.

  DOI：

  10.1002/1521-4184(200203)335:2/3<94::aid-ardp94>3.0.co;2-w

文献信息

• Chloramphenicol base chemistry. Part 10 1 : Asymmetric synthesis of α -hydroxy chiral alcohols via intramolecular Michael additions of γ -hydroxy- α , β -unsaturated enones with chloramphenicol base derived bifunctional urea organocatalysts
  作者：Haifeng Wang、Linjie Yan、Yan Wu、Fener Chen

  DOI：10.1016/j.tet.2017.03.076

  日期：2017.5

  γ-hydroxy-α, β-unsaturated enones. The oxidation of the resulting products provided facile access to the corresponding α-hydroxy chiral alcohols with good efficiency and enantioselectivity, with the reaction displaying broad substrate scope. The utility of this methodology was further demonstrated by the synthesis of (R)-2-hydroxy-4-phenylbutanoate, which is a key building block for the construction of the ACE

  我们已经开发了氯霉素碱脲催化的γ-羟基-α，β-不饱和烯酮的分子内迈克尔加成。所得产物的氧化提供了以良好的效率和对映选择性容易地获得相应的α-羟基手性醇的反应，该反应显示出广泛的底物范围。通过合成（R）-2-羟基-4-苯基丁酸（R）-2-羟基-4-苯基丁酸酯进一步证明了该方法的实用性，这是构建ACE抑制剂盐酸贝那普利的关键组成部分。
• Synthesis and Antimicrobial Activity of Hydroxyalkyl- and Hydroxyacyl-phenols and Their Benzyl Ethers
  作者：Jürgen Krauß、D. Unterreitmeier

  DOI：10.1002/1521-4184(200203)335:2/3<94::aid-ardp94>3.0.co;2-w

  日期：2002.3

  New phenolic compounds with hydrophilic side chains were prepared from 4-benzyloxybenzaldehyde and alkenyl magnesium bromides, followed by Sharpless dihydroxylation and hydrogenolytic removal of the benzyl group. The resulting compounds were tested in an agar diffusion assay against gram positive bacteria, gram negative bacteria, and against the fungi Candida glabrata and Aspergillus niger.