2-iodohydroquinone diacetate | 496881-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2-iodohydroquinone diacetate
• 英文别名: 1,4-diacetoxy-2-iodo-benzene；(Jod-p-phenylen)-diacetat；1,4-Diacetoxy-2-jod-benzol；(4-Acetyloxy-3-iodophenyl) acetate
• CAS: 496881-71-1
• 化学式: C₁₀H₉IO₄
• 分子量: 320.084
• InChiKey: VQBDHGNIBSNKCE-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±37.0 °C(Predicted)
• 密度：
  1.713±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-iodohydroquinone diacetate 在 四(三苯基膦)钯 lithium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.5h， 生成 干蠕孢菌素
  参考文献：
  名称：

  Synthesis and Structure−Phytotoxicity Relationships of Acetylenic Phenols and Chromene Metabolites, and Their Analogues, from the Grapevine Pathogen Eutypa lata

  摘要：

  Eutypa lata, the fungus responsible for dying-arm disease in grapevines, produces a number of structurally related secondary metabolites, of which eutypine (1) has been implicated as the principal phytotoxin. However, analysis of an E. lata strain from California known to be pathogenic to grapevines showed that eutypine was not present, suggesting that other metabolites could be phytotoxic. Investigation of the relative phytotoxicities of individual metabolites has been limited by insufficient material and lack of a reliable bioassay. Metabolites of particular interest and their precursors were therefore synthesized, and a rapid, quantitative bioassay via topical application of individual compounds to disks of grape leaves and measurement of chlorophyll loss was developed to provide a relative measure of tissue damage. The recently reported metabolite eulatachromene (2) was found to have phytotoxicity greater than that of eutypine (1). The cyclization product, 5-formyl-2-methylvinyl[1]benzofuran (3), also showed significant activity, whereas the reduction product, eutypinol (4), was inactive, as was the quinol, siccayne (5). These results indicate that before strains of Eutypa are incriminated as pathogenic they must be analyzed for the presence or absence of specific constituents for which the phytotoxicity has been unequivocally established.

  DOI：

  10.1021/np020415t
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 2-iodohydroquinone diacetate
  参考文献：
  名称：

  An Optical Method for the Study of Reversible Organic Oxidation—Reduction Systems. III. Preparation and Use of a New Optically Active Standard

  摘要：

  DOI：

  10.1021/ja01318a039

文献信息

• Synthesis and Structure−Phytotoxicity Relationships of Acetylenic Phenols and Chromene Metabolites, and Their Analogues, from the Grapevine Pathogen <i>Eutypa </i><i>l</i><i>ata</i>
  作者：Leverett R. Smith、Noreen Mahoney、Russell J. Molyneux

  DOI：10.1021/np020415t

  日期：2003.2.1

  Eutypa lata, the fungus responsible for dying-arm disease in grapevines, produces a number of structurally related secondary metabolites, of which eutypine (1) has been implicated as the principal phytotoxin. However, analysis of an E. lata strain from California known to be pathogenic to grapevines showed that eutypine was not present, suggesting that other metabolites could be phytotoxic. Investigation of the relative phytotoxicities of individual metabolites has been limited by insufficient material and lack of a reliable bioassay. Metabolites of particular interest and their precursors were therefore synthesized, and a rapid, quantitative bioassay via topical application of individual compounds to disks of grape leaves and measurement of chlorophyll loss was developed to provide a relative measure of tissue damage. The recently reported metabolite eulatachromene (2) was found to have phytotoxicity greater than that of eutypine (1). The cyclization product, 5-formyl-2-methylvinyl[1]benzofuran (3), also showed significant activity, whereas the reduction product, eutypinol (4), was inactive, as was the quinol, siccayne (5). These results indicate that before strains of Eutypa are incriminated as pathogenic they must be analyzed for the presence or absence of specific constituents for which the phytotoxicity has been unequivocally established.
• An Optical Method for the Study of Reversible Organic Oxidation—Reduction Systems. III. Preparation and Use of a New Optically Active Standard
  作者：D. E. Kvalnes

  DOI：10.1021/ja01318a039

  日期：1934.3