(2,4-dihydroxy-benzylidene)-dimethyl-ammonium; dichloro phosphate

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2,4-dihydroxy-benzylidene)-dimethyl-ammonium; dichloro phosphate
• 英文别名: (2,4-Dihydroxy-benzyliden)-dimethyl-ammonium; Dichlorophosphat；(2,4-Dihydroxybenzylidene)dimethylammonium dichlorophosphinate；dichlorophosphinate;(2,4-dihydroxyphenyl)methylidene-dimethylazanium
• 化学式: C₉H₁₂NO₂*Cl₂O₂P
• 分子量: 300.078
• InChiKey: RHORPWLHLOJYQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2,4-dihydroxy-benzylidene)-dimethyl-ammonium; dichloro phosphate 在 Lipase Amano PS 、 水 、 potassium carbonate 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 59.5h， 生成 (-)-(R)-5,7-dimethoxyethoxymethyloxy-2-acetoxymethyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Enantioselective acylation of 2-hydroxymethyl-2,3-dihydrobenzofurans catalysed by lipase from Pseudomonas cepacia (Amano PS) and total stereoselective synthesis of (−)-(R)-MEM-protected arthrographol

  摘要：

  Lipase Amano PS catalysed acylation of (+/-)-2-hydroxymethyl-2,3-dihydrobenzofurans using vinyl acetate as the acyl donor in n-hexane gave (-)-(R)-2-acetoxymethyl-2,3-dihydrobenzo and (+)-(S)-2-hydroxymethyl-2,3-dihydrobenzofurans in high enantiomeric excess. (-)-(R)-Acetate 18j is converted to (-)-(R)-MEM-protected arthrographol 22. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00302-5
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 间苯二酚 在 三氯氧磷 作用下， 生成 (2,4-dihydroxy-benzylidene)-dimethyl-ammonium; dichloro phosphate
  参考文献：
  名称：

  Vilsmeier-Haack 反应制备 2,4-二羟基苯甲醛

  摘要：

  摘要 已开发出一种通过 Vilsmeier-Haack 反应从间苯二酚有效合成 2,4-二羟基苯甲醛 (1) 的方法。磷酰氯/DMF 或草酰氯/DMF 以 65-75% 的产率生成 1。中间体甲脒盐已被表征。

  DOI：

  10.1080/00397919608003654

文献信息

• Preparation of 2,4-Dihydroxybenzaldehyde by the Vilsmeier-Haack Reaction
  作者：Wilford L. Mendelson、Stuart Hayden

  DOI：10.1080/00397919608003654

  日期：1996.2

  Abstract An efficient synthesis of 2,4-dihydroxybenzaldehyde (1) from resorcinol via the Vilsmeier-Haack reaction has been developed. Either phosphorous oxychloride/DMF or oxalyl chloride/DMF produces 1 in yields of 65–75%. The intermediate formamidinium salts have been characterized.

  摘要 已开发出一种通过 Vilsmeier-Haack 反应从间苯二酚有效合成 2,4-二羟基苯甲醛 (1) 的方法。磷酰氯/DMF 或草酰氯/DMF 以 65-75% 的产率生成 1。中间体甲脒盐已被表征。
• Mangoni, Annali di Chimica, 1958, vol. 48, p. 930,933 Anm.8,937
  作者：Mangoni

  DOI：——

  日期：——
• 2,4-dihydroxy benzaldehyde derived Schiff bases as small molecule Hsp90 inhibitors: Rational identification of a new anticancer lead
  作者：Sayan Dutta Gupta、B. Revathi、Gisela I. Mazaira、Mario D. Galigniana、C.V.S. Subrahmanyam、N.L. Gowrishankar、N.M. Raghavendra

  DOI：10.1016/j.bioorg.2015.02.003

  日期：2015.4

  Hsp90 is a molecular chaperone that heals diverse array of biomolecules ranging from multiple oncogenic proteins to the ones responsible for development of resistance to chemotherapeutic agents. Moreover they are over-expressed in cancer cells as a complex with co-chaperones and under-expressed in normal cells as a single free entity. Hence inhibitors of Hsp90 will be more effective and selective in destroying cancer cells with minimum chances of acquiring resistance to them. In continuation of our goal to rationally develop effective small molecule azomethines against Hsp90, we designed few more compounds belonging to the class of 2,4-dihydroxy benzaldehyde derived imines (1-13) with our validated docking protocol. The molecules exhibiting good docking score were synthesized and their structures were confirmed by IR, H-1 NMR and mass spectral analysis. Subsequently, they were evaluated for their potential to suppress Hsp90 ATPase activity by Malachite green assay. The antiproliferative effect of the molecules were examined on PC3 prostate cancer cell lines by adopting 3-(4,5-dimethythiazol-2yl)-2,5-diphenyl tetrazolium bromide (MTT) assay methodology. Finally, schiff base 13 emerged as the lead molecule for future design and development of Hsp90 inhibitors as anticancer agents. (C) 2015 Elsevier Inc. All rights reserved.
• Enantioselective acylation of 2-hydroxymethyl-2,3-dihydrobenzofurans catalysed by lipase from Pseudomonas cepacia (Amano PS) and total stereoselective synthesis of (−)-(R)-MEM-protected arthrographol
  作者：S Ramadas、G.L.David Krupadanam

  DOI：10.1016/s0957-4166(00)00302-5

  日期：2000.8

  Lipase Amano PS catalysed acylation of (+/-)-2-hydroxymethyl-2,3-dihydrobenzofurans using vinyl acetate as the acyl donor in n-hexane gave (-)-(R)-2-acetoxymethyl-2,3-dihydrobenzo and (+)-(S)-2-hydroxymethyl-2,3-dihydrobenzofurans in high enantiomeric excess. (-)-(R)-Acetate 18j is converted to (-)-(R)-MEM-protected arthrographol 22. (C) 2000 Published by Elsevier Science Ltd.