6'-acetoxy-2'-hydroxyacetophenone | 26674-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6'-acetoxy-2'-hydroxyacetophenone
• 英文别名: acetic acid 2-acetyl-3-hydroxyphenyl ester；2-Acetoxy-6-hydroxy-acetophenon；2',6'-Dihydroxyacetophenone, acetate；(2-acetyl-3-hydroxyphenyl) acetate
• CAS: 26674-05-5
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: FYAUIMDHUAKCPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6'-acetoxy-2'-hydroxyacetophenone 在 phenyltrimethylammonium tribromide 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 9.0h， 生成 (Z)-4-hydroxy-2-benzylidenebenzofuran-3(2H)-one
  参考文献：
  名称：

  Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase

  摘要：

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

  DOI：

  10.1021/jm200242p
• 作为产物：
  描述：

  2,6-diacetoxyacetophenone 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 以87%的产率得到6'-acetoxy-2'-hydroxyacetophenone
  参考文献：
  名称：

  BF3·OEt2 mediated regioselective deacetylation of polyacetoxyacetophenones and its application in the synthesis of natural products

  摘要：

  We have developed an efficient method to regioselectively deacetylate polyacetoxyacetophenones using BF(3)center dot OEt(2) in excellent yields and demonstrated the application of the procedure in the synthesis of natural products. (C) 2008 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.020

文献信息

• Diels–Alder reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethane. New synthesis of benzo[b]xanthones
  作者：Angela Sandulache、Artur M.S Silva、José A.S Cavaleiro

  DOI：10.1016/s0040-4020(01)01131-0

  日期：2002.1

  efficient new route to the benzo[b]xanthone system has been developed and applied to the synthesis of several new derivatives. The cycloaddition reactions of chromone-3-carboxaldehydes 12, reacting as dienophiles, with ortho-benzoquinodimethane 7 gave a diastereomeric mixture of cycloadducts 8 and 9. The formation of these compounds results from the Diels–Alder reactions of 12 and 7 followed by the in

  已开发出一种有效的苯并[ b ]吨蒽酮体系新途径，并将其应用于几种新衍生物的合成。色酮-3-羧醛12的环加成反应（作为亲二烯体）与邻-苯并醌二甲烷7反应，得到环加合物8和9的非对映异构体混合物。这些化合物的形成是由12和7的Diels–Alder反应以及随后的原位甲酰化作用引起的。在碘的存在下，用二甲基亚砜氧化加合物8和9生成了新颖的苯并[ b ]氧杂蒽11 丰产。
• A process for the production of 2-alkyl- or 2-alkenyl-4,6-diacetyl resorcinols; 2-allyl-4,6-diacetyl resorcinol
  申请人：FISONS plc

  公开号：EP0012512A1

  公开（公告）日：1980-06-25

  2-Alkyl- or 2-Alkenyl-4,6-diacetyl resorcinols of the formula in which R1 is alkyl C 1 to 6, e.g. isopropyl, or alkenyl C 2 to 6, e.g. allyl, are obtained by reacting 4,6-diacetylresorcinol with a corresponding alkyl or alkenyl halide. The reaction is carried out preferably at a temperature of from 20 to 120° C, in a polar hydrogen bonding solvent, e.g. water, and in the presence of a base. The product 4,6-diacetyl resorcinols are useful as intermediates in the production of certain bezodipyran-dicarboxylic acids, which are of known utility as pharmaceuticals. Certain of the product 4,6-diacetyl resorcinols are novel.

  式中的 2-烷基-或 2-烯基-4,6-二乙酰基间苯二酚，其中 R1 为 C 1-6 烷基（如异丙基）或 C 2-6 烯基（如烯丙基）。 其中 R1 为 C 1-6 烷基（如异丙基）或 C 2-6 烯基（如烯丙基）的间苯二酚与相应的烷基或烯基卤化物反应而得。反应最好在 20 至 120 摄氏度的温度下、极性氢键溶剂（如水）中和碱存在下进行。产物 4,6-二乙酰基间苯二酚可用作生产某些已知可用作药物的苯并二吡喃二羧酸的中间体。某些 4,6-二乙酰基间苯二酚产品具有新颖性。
• Lipoxygenase inhibitors
  申请人：MERCK FROSST CANADA INC.

  公开号：EP0146243A1

  公开（公告）日：1985-06-26

  Compounds of the general Formula I: wherein Z is a bond, CR14=CR15 or CHR14-CHR15; X is O, S, SO, or S02 R1, R2, R3, R4, T, V are as defined in the prescription; and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit the mammalian 5-lipoxygenase enzyme, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders. The compounds are made into suitable pharmaceutical compositions for administration to patients. Certain of the compounds are novel.

  通式 I 的化合物：其中 Z 是键、CR14=CR15 或 CHR14-CHR15；X 是 O、S、SO 或 S02 R1、R2、R3、R4、T、V 如处方中所定义；及其药学上可接受的盐是白三烯生物合成的抑制剂。 这些化合物可抑制哺乳动物的 5-脂氧合酶，从而阻止花生四烯酸代谢为白三烯。 因此，这些化合物可用于治疗哮喘、过敏性疾病、炎症、皮肤病和某些心血管疾病。 这些化合物可制成适当的药物组合物给患者用药。 某些化合物是新型的。
• TMSI-Promoted Vinylogous Michael Addition of Siloxyfuran to 2-Substituted Chromones: A General Approach for the Total Synthesis of Chromanone Lactone Natural Products
  作者：Jie Liu、Zhanchao Li、Pei Tong、Zhixiang Xie、Yuan Zhang、Ying Li

  DOI：10.1021/jo502571r

  日期：2015.2.6

  A concise and facile synthetic protocol for the construction of the 2-gamma-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (+/-)-microdiplodiasone, (+/-)-lachnone C, and (+/-)-gonytolides C and G.
• LAU C. K.; BELANGER P. C.; DUFRESNE C.; SCHEIGETZ J., J. ORG. CHEM., 52,(1987) N 9, 1670-1673
  作者：LAU C. K.、 BELANGER P. C.、 DUFRESNE C.、 SCHEIGETZ J.

  DOI：——

  日期：——