5-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one | 848653-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one
• 英文别名: 5-[(3,4,5-Trimethoxyphenyl)methyl]oxolan-2-one
• CAS: 848653-55-4
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: GUJNKRPGTDQPIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以45%的产率得到(-)-5-(3',4',5'-Trihydroxyphenyl)-γ-valerolactone
  参考文献：
  名称：

  呋喃基二烯氧基硅烷的催化，对映选择性长春Mukaiyama Aldol反应：γ-戊内酯Flavan-3-ol代谢物和δ-内酯类似物的化学发散方法

  摘要：

  从2-甲硅烷氧基呋喃和烷氧基取代的苯甲醛作为常见的前体开始，实现了一组羟苯基γ-戊内酯的不对称合成。关键的合成步骤包括对映选择性的乙烯基Mukaiyama aldol反应和Barton-McCombie脱氧反应。通过5–6个步骤获得了5个对映体富集的γ-戊内酯目标，总产率为18–63％，ee为82–98％，这为直接进入此类具有生物有效性且难得的flavan -3-ol代谢物铺平了道路。同时，偶然发现了一种空前的一锅还原环扩展过程，从酚丁醇化物前体产生外消旋的δ-内酯类似物。

  DOI：

  10.1002/adsc.201500705
• 作为产物：
  描述：

  1-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 sodium carbonate 、 copper(II) sulfate 、 丙酸 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 生成 5-(3,4,5-trimethoxybenzyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives

  摘要：

  Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 muM. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.070

文献信息

• Catalytic, Enantioselective Vinylogous Mukaiyama Aldol Reaction of Furan-Based Dienoxy Silanes: A Chemodivergent Approach to γ-Valerolactone Flavan-3-ol Metabolites and δ-Lactone Analogues
  作者：Claudio Curti、Nicoletta Brindani、Lucia Battistini、Andrea Sartori、Giorgio Pelosi、Pedro Mena、Furio Brighenti、Franca Zanardi、Daniele Del Rio

  DOI：10.1002/adsc.201500705

  日期：2015.12.14

  a set of hydroxyphenyl γ-valerolactones was achieved starting from 2-silyloxyfuran and alkoxy-substituted benzaldehydes as common precursors. Key synthesis steps included an enantioselective vinylogous Mukaiyama aldol reaction and a Barton–McCombie deoxygenation. Five enantioenriched γ-valerolactone targets were obtained in 5–6 steps, 18–63% overall yields and 82–98 % ee, paving the way for the straightforward

  从2-甲硅烷氧基呋喃和烷氧基取代的苯甲醛作为常见的前体开始，实现了一组羟苯基γ-戊内酯的不对称合成。关键的合成步骤包括对映选择性的乙烯基Mukaiyama aldol反应和Barton-McCombie脱氧反应。通过5–6个步骤获得了5个对映体富集的γ-戊内酯目标，总产率为18–63％，ee为82–98％，这为直接进入此类具有生物有效性且难得的flavan -3-ol代谢物铺平了道路。同时，偶然发现了一种空前的一锅还原环扩展过程，从酚丁醇化物前体产生外消旋的δ-内酯类似物。
• Chemo-, Regio- and Stereoselective Heck Arylation of Allylated Malonates: Mechanistic Insights by ESI-MS and Synthetic Application toward 5-Arylmethyl-γ-lactones
  作者：Caio C. Oliveira、Marcelo V. Marques、Marla N. Godoi、Thaís Regiani、Vanessa G. Santos、Emerson A. F. dos Santos、Marcos N. Eberlin、Marcus M. Sá、Carlos R. D. Correia

  DOI：10.1021/ol502529v

  日期：2014.10.3

  We describe herein a general method for the controlled Heck arylation of allylated malonates. Both electron-rich and electron-poor aryldiazonium salts were readily employed as the aryl-transfer agents in good yields and in high chemo-, regio-, and stereoselectivity without formation of decarboxylated byproducts. Reaction monitoring via ESI-MS was used to support the formation of chelated Pd species

  我们在本文中描述了控制烯丙基化丙二酸酯的Heck芳基化的一般方法。富电子和贫电子的芳基重氮盐都容易以高收率和高化学，区域和立体选择性用作芳基转移剂，而不会形成脱羧副产物。通过ESI-MS进行的反应监测用于支持通过催化循环形成螯合的Pd物质。另外，一些Heck加合物已成功用于药理活性γ-内酯的全合成。
• Synthesis and biological activity of the tea catechin metabolites, M4 and M6 and their methoxy-derivatives
  作者：Joshua D. Lambert、Joseph E. Rice、Jungil Hong、Zhe Hou、Chung S. Yang

  DOI：10.1016/j.bmcl.2004.12.070

  日期：2005.2

  Syntheses are reported for metabolites M4 (1) and M6 (2) of the green tea polyphenols epicatechin (EC) and epigallocatechin (EGC) and their gallate derivatives. Several methoxy-derivatives of 1 and 2 were also prepared. Compounds 1 and 2 were evaluated for growth inhibitory activity against a panel of immortalized and malignant human cell lines with 1 being the more active compound. The possible antiinflammatory activity of 1 and its trimethoxy derivative was also evaluated. Neither compound inhibited the release of arachidonic acid, although 1 inhibited NO production by 50% at 20 muM. (C) 2005 Elsevier Ltd. All rights reserved.
• Ligand‐Enabled Ni^II‐Catalyzed Hydroxylarylation of Alkenes with Molecular Oxygen
  作者：Dao‐Ming Wang、Li‐Qin She、Hao Yuan、Yichen Wu、Yong Tang、Peng Wang

  DOI：10.1002/anie.202304573

  日期：2023.8.28

  The use of molecular oxygen as the terminal oxidant in transition metal catalyzed oxidative process is an appealing and challenging task in organic synthetic chemistry. Here, we report a Ni‐catalyzed hydroxylarylation of unactivated alkenes enabled by a β‐diketone ligand with high efficiency and excellent regioselectivity employing molecular oxygen as the oxidant and hydroxyl source. This reaction features mild conditions, broad substrate scope and incredible heterocycle compatibility, providing a variety of β‐hydroxylamides, γ‐hydroxylamides, β‐aminoalcohols, γ‐aminoalcohols, and 1,3‐diols in high yields. The synthetic value of this methodology was demonstrated by the efficient synthesis of two bioactive compounds, (±)‐3′‐methoxyl citreochlorol and tea catechin metabolites M4.

  摘要在过渡金属催化的氧化过程中使用分子氧作为末端氧化剂是有机合成化学中一项既吸引人又具有挑战性的任务。在此，我们报告了一种镍催化的未活化烯烃羟基芳基化反应，该反应以分子氧为氧化剂和羟基源，由β-二酮配体促成，具有高效率和优异的区域选择性。该反应具有条件温和、底物范围广、杂环兼容性强等特点，能以高产率提供各种 β-羟基酰胺、γ-羟基酰胺、β-氨基醇、γ-氨基醇和 1,3-二醇。(±)-3′-methoxyl citreochlorol 和茶儿茶素代谢物 M4 这两种生物活性化合物的高效合成证明了该方法的合成价值。