3,4-dimethoxy-5-nitrobenzyl chloride | 42877-11-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dimethoxy-5-nitrobenzyl chloride
• 英文别名: 5-(Chloromethyl)-1,2-dimethoxy-3-nitrobenzene
• CAS: 42877-11-2
• 化学式: C₉H₁₀ClNO₄
• 分子量: 231.636
• InChiKey: WFSXLEKNOFWVRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dimethoxy-5-nitrobenzyl chloride 在 Ru-carbon potassium tert-butylate 、 氢溴酸 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 5-氟多巴
  参考文献：
  名称：

  Syntheses of 5-fluoro-d/l-dopa and [18F]5-fluoro-l-dopa

  摘要：

  This paper describes the synthesis of 5-fluoro-D/L-dopa and the corresponding [F-18]5-fluoro-L-dopa starting from 5-nitrovanillin via malonic ester synthesis, the Balz-Schiemann reaction and the separation of the racemic mixture [F-18]5-fluoro-D/L-dopa with a chiral HPLC system. The inactive 5-fluoro-D/L-dopa was obtained in an eight-step synthesis with an overall yield of 10%. For a reliable synthesis, the nitro group was reduced with hydrazine hydrate and ruthenium on charcoal.

  DOI：

  10.1016/0022-1139(93)03032-h
• 作为产物：
  描述：

  5-nitroveratral 在 盐酸 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 生成 3,4-dimethoxy-5-nitrobenzyl chloride
  参考文献：
  名称：

  Syntheses of 5-fluoro-d/l-dopa and [18F]5-fluoro-l-dopa

  摘要：

  This paper describes the synthesis of 5-fluoro-D/L-dopa and the corresponding [F-18]5-fluoro-L-dopa starting from 5-nitrovanillin via malonic ester synthesis, the Balz-Schiemann reaction and the separation of the racemic mixture [F-18]5-fluoro-D/L-dopa with a chiral HPLC system. The inactive 5-fluoro-D/L-dopa was obtained in an eight-step synthesis with an overall yield of 10%. For a reliable synthesis, the nitro group was reduced with hydrazine hydrate and ruthenium on charcoal.

  DOI：

  10.1016/0022-1139(93)03032-h

文献信息

• Synthesis of 3,4-dihydroxy-5-fluoro-DL-phenylalanine and 3,4-dihydroxy-5-[fluorine-18]fluoro-DL-phenylalanine
  作者：Gunter Firnau、Claude Nahmias、Stephen Garnett

  DOI：10.1021/jm00262a026

  日期：1973.4
• Syntheses of 5-fluoro-d/l-dopa and [18F]5-fluoro-l-dopa
  作者：Mario Argentini、Claudia Wiese、Regin Weinreicht

  DOI：10.1016/0022-1139(93)03032-h

  日期：1994.8

  This paper describes the synthesis of 5-fluoro-D/L-dopa and the corresponding [F-18]5-fluoro-L-dopa starting from 5-nitrovanillin via malonic ester synthesis, the Balz-Schiemann reaction and the separation of the racemic mixture [F-18]5-fluoro-D/L-dopa with a chiral HPLC system. The inactive 5-fluoro-D/L-dopa was obtained in an eight-step synthesis with an overall yield of 10%. For a reliable synthesis, the nitro group was reduced with hydrazine hydrate and ruthenium on charcoal.