4-acetoxy-3-(3'-methylbut-3'-en-1'-ynyl)benzaldehyde | 168132-67-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-acetoxy-3-(3'-methylbut-3'-en-1'-ynyl)benzaldehyde
• 英文别名: Benzaldehyde, 4-(acetyloxy)-3-(3-methyl-3-buten-1-ynyl)-；[4-formyl-2-(3-methylbut-3-en-1-ynyl)phenyl] acetate
• CAS: 168132-67-0
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: KCBMUYVRPPTFCK-UHFFFAOYSA-N

物化性质

• 沸点：
  368.2±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-acetoxy-3-(3'-methylbut-3'-en-1'-ynyl)benzaldehyde 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以56%的产率得到4-羟基-3-(3-甲基-3-丁烯-1-炔基)苯甲醛
  参考文献：
  名称：

  钯催化偶联反应合成酚类天然产物

  摘要：

  Derivatives of 2,4-diiodophenol are shown to undergo palladium catalyzed carbonylation and alkyne coupling reactions in excellent to moderate yield and high regioselectivity. The scope of these reactions is explored. Palladium catalyzed reactions are employed as the key steps in the synthesis of three phenolic natural products: Plicatin B, Drupanin and Eutypine.

  DOI：

  10.1016/0040-4020(95)00441-a
• 作为产物：
  描述：

  4-羟基-3-碘苯甲醛 在 四(三苯基膦)钯 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 23.1h， 生成 4-acetoxy-3-(3'-methylbut-3'-en-1'-ynyl)benzaldehyde
  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

文献信息

• [EN] METHODS FOR CONTROLLING FUNGAL PATHOGENS<br/>[FR] PROCEDES D'ELIMINATION DE PATHOGENES FONGIQUES
  申请人：SUMMUS GROUP LTD

  公开号：WO2001001977A1

  公开（公告）日：2001-01-11

  The invention is directed to methods and compositions for controlling fungal pathogens. The compositions comprise a compound having fungicidal activity and one of the formulas: (I), (II), (III), (IV).
• 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.
• Synthesis of phenolic natural products using palladium catalyzed coupling reactions
  作者：Roderick W. Bates、Christine J. Gabel、Jianhua Ji、Thota Rama-Devi

  DOI：10.1016/0040-4020(95)00441-a

  日期：1995.7

  Derivatives of 2,4-diiodophenol are shown to undergo palladium catalyzed carbonylation and alkyne coupling reactions in excellent to moderate yield and high regioselectivity. The scope of these reactions is explored. Palladium catalyzed reactions are employed as the key steps in the synthesis of three phenolic natural products: Plicatin B, Drupanin and Eutypine.

表征谱图