2-[acetoxy(phenyl)methyl]phenyl acetate | 55190-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[acetoxy(phenyl)methyl]phenyl acetate
• 英文别名: [2-[acetyloxy(phenyl)methyl]phenyl] acetate
• CAS: 55190-57-3
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: UYCGUIXDBWRPTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[acetoxy(phenyl)methyl]phenyl acetate 、 1-(2-(4-chlorophenyl)-2-oxoethyl)pyridinium bromide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以76%的产率得到trans-(4-chlorophenyl)(3-phenyl-2,3-dihydrobenzofuran-2-yl)methanone
  参考文献：
  名称：

  作为新型α-葡萄糖苷酶抑制剂的2-芳基-4 H-色烯和3-芳基-1 H-苯并[ f ]色烯衍生物的合成，体外和体内评价

  摘要：

  在本文中，我们报告了一种新型的芳基亚甲基衍生物的研究，该衍生物是具有突出的α-葡萄糖苷酶抑制特性的天然类黄酮的类似物。通过简单的逐步计算机筛选，有效合成和生物学评估来鉴定新型抑制剂。显示2-芳基-4H-亚甲基核心保留药效基团性质，同时易于合成获得。通过筛选鉴定出的先导化合物可抑制酵母α-葡萄糖苷酶，IC 50为62.26 µM，可防止2.2 mg / kg剂量的大鼠餐后高血糖。

  DOI：

  10.1016/j.bmcl.2018.10.018
• 作为产物：
  描述：

  2-羟基二苯甲酮 、 乙酸酐 生成 2-[acetoxy(phenyl)methyl]phenyl acetate
  参考文献：
  名称：

  Photochemical transformations of small ring heterocyclic compounds. LXII. Competitive keto-enolate photochemistry in the 3-phenylcoumaran-2-one system

  摘要：

  DOI：

  10.1021/ja00840a040

文献信息

• Reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans into 2-hydroxydihydrochalcones and flav-2-enes
  作者：Dmitry V. Osipov、Maxim R. Demidov、Vitaly А. Osyanin、Yuri N. Klimochkin

  DOI：10.1007/s10593-021-03039-6

  日期：2021.12

  4-diaryl-substituted 4H-chromenes by the formal [4+1] cycloaddition reaction of o-quinone methides and pyridinium ylides followed by reductive rearrangement of 2-aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid or samarium and trimethylchlorosilane in 1,4-dioxane. The reduction of 3-unsubstituted 2-aroyl-2,3-dihydrobenzofurans by the action of zinc in acetic acid leads mainly to 2-hydroxydihydrochalcones

  提出了通过邻醌甲基化物和吡啶鎓叶立德的形式 [4+1] 环加成反应然后还原重排合成 2-芳基和 2,4-二芳基取代的 4 H-色烯的两步程序。 2-芳酰基-2,3-二氢苯并呋喃通过乙酸中的锌或钐和 1,4-二恶烷中的三甲基氯硅烷的作用。通过乙酸中锌的作用还原 3-未取代的 2-芳酰基-2,3-二氢苯并呋喃主要产生 2-羟基二氢查耳酮。
• Synthesis and biological evaluation of 2-acylbenzofuranes as novel α-glucosidase inhibitors with hypoglycemic activity
  作者：Alexander A. Spasov、Denis A. Babkov、Tatyana Yu Prokhorova、Ekaterina A. Sturova、Diana R. Muleeva、Maxim R. Demidov、Dmitry V. Osipov、Vitaly A. Osyanin、Yuri N. Klimochkin

  DOI：10.1111/cbdd.13038

  日期：2017.12

  A series of benzofuran derivatives was synthesized as analogues of known natural α‐glucosidase inhibitors. Their activity was evaluated in enzymatic assay and in rat model of diabetes mellitus. Newly identified inhibitors demonstrate significant potency with IC50 values ranging from 6.50 to 722.2 μm, as well as hypoglycemic activity exceeding the reference drug acarbose. Docking simulations provided insight into structure‐activity relationships to direct further development of these novel hypoglycemic agents.
• Reactions of <i>o</i>-Quinone Methides with Pyridinium Methylides: A Diastereoselective Synthesis of 1,2-Dihydronaphtho[2,1-<i>b</i>]furans and 2,3-Dihydrobenzofurans
  作者：Vitaly A. Osyanin、Dmitry V. Osipov、Yuri N. Klimochkin

  DOI：10.1021/jo400621r

  日期：2013.6.7

  A simple, general route to the 1,2-dihydronaphtho[2,1-b]furans and 2,3-dihydrobenzofurans substituted at C-2 by an acyl or aryl group, starting from phenolic Mannich bases and pyridinium ylides, has been developed. The mechanism of the reaction is believed to involve the formation of the o-quinone methide intermediate, Michael-type addition of the ylide to the o-quinone methide, followed by intramolecular nucleophilic substitution.