4-甲酰基-2-碘苯酚乙酸酯 | 166803-90-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 4-甲酰基-2-碘苯酚乙酸酯
• 英文名称: 4-acetoxy-3-iodobenzaldehyde
• 英文别名: Acetic acid 4-formyl-2-iodo-phenyl ester；(4-formyl-2-iodophenyl) acetate
• CAS: 166803-90-3
• 化学式: C₉H₇IO₃
• 分子量: 290.057
• InChiKey: DJLQTRUNVPCKOF-UHFFFAOYSA-N

物化性质

• 沸点：
  347.8±37.0 °C(Predicted)
• 密度：
  1.803±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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-甲酰基-2-碘苯酚乙酸酯 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 23.0h， 生成 5-formyl-2-isopropenylbenzofuran
  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：

  2,4-二碘苯酚乙酸酯 以40%的产率得到
  参考文献：
  名称：

  Bates Roderick W., Gabel Christine J., Ji Jianhua, Tetrahedron Lett., 35 (1994) N 38, S 6993-6996

  摘要：

  DOI：

文献信息

• Hg(II)-Mediated Intramolecular Cyclization Reaction in Aqueous Media and Its Application as Hg(II) Selective Indicator
  作者：Ananta Kumar Atta、Seul-Bi Kim、Jungseok Heo、Dong-Gyu Cho

  DOI：10.1021/ol4000873

  日期：2013.3.1

  The Hg(II)-specific intramolecular cyclization reaction of ethynyl phenols was carried out for the first time in semiaqueous media at ambient temperature. The reaction unit (ethynyl phenol) was coupled with a malononitrile derivative (signal unit), which afforded the chromogenic Hg(II) indicator 7. The reaction of the chromogenic Hg(II) indicator 7 was further optimized in DMSO/water (3:7, v/v) (10

  乙炔基酚的Hg（II）特异性分子内环化反应是在环境温度下首次在半水介质中进行的。将反应单元（乙炔基苯酚）与丙二腈衍生物（信号单元）偶联，得到发色的Hg（II）指示剂7。在DMSO /水（3：7，v / v）（10 mM PBS缓冲液，pH = 7.0）中进一步优化了生色Hg（II）指示剂7的反应。在Hg（II）存在下，化合物7显示出从蓝色到浅黄色的颜色变化。
• Synthesis of Dihydrobenzofurans via Palladium-Catalyzed Annulation of 1,3-Dienes by <i>o</i>-Iodoaryl Acetates
  作者：Roman V. Rozhkov、Richard C. Larock

  DOI：10.1021/jo100495t

  日期：2010.6.18

  palladium-catalyzed annulation of 1,3-dienes by o-iodoaryl acetates provides an efficient approach to biologically interesting dihydrobenzofurans. The annulation is believed to proceed via (1) oxidative addition of the aryl iodide to Pd(0), (2) syn-addition of the resulting arylpalladium complex to the 1,3-diene, (3) intramolecular coordination of the phenolic oxygen to the Pd center, (4) hydrolysis of the acetyl

  乙酸邻碘芳基酯在钯催化的1,3-二烯上的环化反应提供了一种有效的方法，用于制备生物学上令人关注的二氢苯并呋喃。该环被认为是通过（1）氧化加成的芳基碘化物与Pd（0），（2）进行合成所得的芳基钯配合物与1,3-二烯的-addition，（3）分子内酚氧的协调到Pd中心，（4）乙酰基水解，和（5）Pd（0）的还原消除，从而使催化剂再生。该反应是相当普遍的，区域选择性，立体选择性和，以及各种终端，环状的，和内部1,3-二烯，以及富电子和缺电子ø -iodoaryl乙酸盐，可以使用。
• Regioselective coupling reactions of diiodophenol derivatives
  作者：Roderick W. Bates、Christine J. Gabel、Jianhua Ji

  DOI：10.1016/0040-4039(94)88207-x

  日期：1994.9

  The acetate and t-BOC derivatives of 2,4-diiodophenol undergo regioselective palladium catalyzed coupling reactions. The products are those of para substitution.
• 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.
• [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).