2-Chloro-1-(4-methoxy-3-phenylmethoxyphenyl)ethanone | 171849-65-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Chloro-1-(4-methoxy-3-phenylmethoxyphenyl)ethanone
• 英文别名: 2-chloro-1-(4-methoxy-3-phenylmethoxyphenyl)ethanone
• CAS: 171849-65-3
• 化学式: C₁₆H₁₅ClO₃
• 分子量: 290.746
• InChiKey: RJHDIQRSKMGUPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Chloro-1-(4-methoxy-3-phenylmethoxyphenyl)ethanone 在 sodium hydride 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone
  参考文献：
  名称：

  First chemical synthesis report of an anthocyanin metabolite with in vivo occurrence: cyanidin-4′-O-methyl-3-glucoside

  摘要：

  Anthocyanins are natural polyphenolic compounds with important biological properties. In humans, these compounds are metabolized into different derivatives namely methyl, glucuronyl, and sulfate conjugates. Among these, cyanidin-4'-O-methyl-3-glucoside, already detected in vivo, seems to be an interesting metabolite to be used as standard for biological studies. The lack of suitable standards is a major drawback in biological studies. Bearing this in mind, this work describes a strategy for the chemical synthesis of cyanidin-4'-O-methyl-3-glucoside 9, which involved in the synthesis of the 'Western' and 'Eastern' molecules, namely 2,4-diacetoxy-6-hydroxybenzaldehyde 2 and 2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone 8, respectively. The final step consisted in the Robinson's acidic aldol condensation between 2 and 8 molecules, which after the respective deprotections yield product 9. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.100
• 作为产物：
  描述：

  3,4-二羟基-2'-氯苯乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-Chloro-1-(4-methoxy-3-phenylmethoxyphenyl)ethanone
  参考文献：
  名称：

  First chemical synthesis report of an anthocyanin metabolite with in vivo occurrence: cyanidin-4′-O-methyl-3-glucoside

  摘要：

  Anthocyanins are natural polyphenolic compounds with important biological properties. In humans, these compounds are metabolized into different derivatives namely methyl, glucuronyl, and sulfate conjugates. Among these, cyanidin-4'-O-methyl-3-glucoside, already detected in vivo, seems to be an interesting metabolite to be used as standard for biological studies. The lack of suitable standards is a major drawback in biological studies. Bearing this in mind, this work describes a strategy for the chemical synthesis of cyanidin-4'-O-methyl-3-glucoside 9, which involved in the synthesis of the 'Western' and 'Eastern' molecules, namely 2,4-diacetoxy-6-hydroxybenzaldehyde 2 and 2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone 8, respectively. The final step consisted in the Robinson's acidic aldol condensation between 2 and 8 molecules, which after the respective deprotections yield product 9. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.100

文献信息

• First chemical synthesis report of an anthocyanin metabolite with in vivo occurrence: cyanidin-4′-O-methyl-3-glucoside
  作者：Luís Cruz、Nuno Mateus、Victor de Freitas

  DOI：10.1016/j.tetlet.2013.03.100

  日期：2013.5

  Anthocyanins are natural polyphenolic compounds with important biological properties. In humans, these compounds are metabolized into different derivatives namely methyl, glucuronyl, and sulfate conjugates. Among these, cyanidin-4'-O-methyl-3-glucoside, already detected in vivo, seems to be an interesting metabolite to be used as standard for biological studies. The lack of suitable standards is a major drawback in biological studies. Bearing this in mind, this work describes a strategy for the chemical synthesis of cyanidin-4'-O-methyl-3-glucoside 9, which involved in the synthesis of the 'Western' and 'Eastern' molecules, namely 2,4-diacetoxy-6-hydroxybenzaldehyde 2 and 2-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3'-benzyloxy-4'-methoxyacetophenone 8, respectively. The final step consisted in the Robinson's acidic aldol condensation between 2 and 8 molecules, which after the respective deprotections yield product 9. (C) 2013 Elsevier Ltd. All rights reserved.