3-(3-methoxyphenyl)furan-2,5-dione | 64505-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-methoxyphenyl)furan-2,5-dione
• CAS: 64505-00-6
• 化学式: C₁₁H₈O₄
• 分子量: 204.182
• InChiKey: MVJCWFAIVNKMSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-methoxyphenyl)furan-2,5-dione 在 盐酸 、 aluminum (III) chloride 、 四(三苯基膦)钯 、 18-冠醚-6 、 potassium tert-butylate 、 potassium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 2-[[6-[[4-(3-Methoxyphenyl)-3-(4-methylphenyl)-6-oxopyridazin-1-yl]methyl]-5,6,7,8-tetrahydronaphthalen-1-yl]oxy]acetic acid
  参考文献：
  名称：

  Discovery of a new series of potent prostacyclin receptor agonists with in vivo activity in rat

  摘要：

  The design and synthesis of two closely related series of prostacyclin receptor agonist compounds that showed excellent human IP receptor potency and efficacy is described. Compounds from this series showed in vivo activity after SC dosing in the monocrotaline model of PAH in rat. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.024
• 作为产物：
  描述：

  (E)-2-(3-Methoxy-phenyl)-but-2-enedioic acid 在 乙酸酐 作用下， 反应 12.0h， 以2858 mg的产率得到3-(3-methoxyphenyl)furan-2,5-dione
  参考文献：
  名称：

  CP-263,114综合研究。通过铑类胡萝卜素C–H插入构建异捻烷环系统

  摘要：

  描述了铑类胡萝卜素C–H的插入策略，该结构用于构造异twistane环系统，该过程需要后期碎裂以实现CP-263,114的全合成。

  DOI：

  10.1016/s0040-4020(02)00664-6

文献信息

• Arylmaleic anhydrides via Heck arylation of fumaric acid
  作者：Alexander I. Roshchin

  DOI：10.1016/j.tetlet.2010.05.023

  日期：2010.7

  Palladium-catalyzed arylation of fumaric acid with aryl iodides is found to be a very simple, economic and scalable approach to arylmaleic anhydrides. The reaction is facilitated by the presence of donor moieties on the aryl fragment and does not occur with strong acceptor groups.

  发现富马酸与芳基碘化物的钯催化的芳基化是一种非常简单，经济且可扩展的制备芳基马来酸酐的方法。芳基片段上供体部分的存在促进了该反应，并且在强受体基团上不发生该反应。
• Divergent Total Syntheses of Enmein‐Type Natural Products: (−)‐Enmein, (−)‐Isodocarpin, and (−)‐Sculponin R
  作者：Saiyong Pan、Sicong Chen、Guangbin Dong

  DOI：10.1002/anie.201803709

  日期：2018.5.22

  Divergent total syntheses of the enmein‐type natural products (−)‐enmein, (−)‐isodocarpin, and (−)‐sculponin R have been achieved in a concise fashion. Key features of the strategy include 1) an efficient early‐stage cage formation to control succeeding diastereoselectivity, 2) a one‐pot acylation/akylation/lactonization to construct the C‐ring and C8 quarternary center, 3) a reductive alkenylation

  enmein型天然产物（-）-enmein，（-）-isodocarpin和（-）-sculponin R的不同总合成方法已经很简洁。该策略的主要特征包括：1）有效的早期笼形结构，以控制后续的非对映选择性； 2）单锅酰化/烷基化/内酯化，以构建C环和C8季中心； 3）还原性烯基化方法，以构建主要的D / E环和4）灵活的路线以允许对三种天然产物进行不同的合成。
• Single-Step Synthesis of γ-Ketoacids through a Photoredox-Catalyzed Dual Decarboxylative Coupling of α-Oxo Acids and Maleic Anhydrides
  作者：Alex M. Davies、Shrikant S. Londhe、Emma R. Smith、Jon A. Tunge

  DOI：10.1021/acs.orglett.3c03258

  日期：2023.12.8

  A photocatalytic methodology for the single step synthesis of γ-ketoacids from α-ketoacids has been developed. This method employs maleic anhydrides as traceless synthetic equivalents of acrylic acids, achieving a selective cross-coupling via a dual decarboxylative strategy, where molecular CO2 is released as the only waste byproduct. The method has also been expanded to incorporate a highly regioselective

  开发了一种从 α-酮酸一步合成 γ-酮酸的光催化方法。该方法采用马来酸酐作为丙烯酸的无痕合成等价物，通过双重脱羧策略实现选择性交叉偶联，其中分子CO 2作为唯一的废物副产物被释放。该方法还得到了扩展，可将高度区域选择性的三组分与各种醇偶联，以获得功能化的 γ-酮酯。
• Synthesis and Pharmacological Characterization of Bicyclic Triple Reuptake Inhibitor 3-Aryl Octahydrocyclopenta[<i>c</i>]pyrrole Analogues
  作者：Liming Shao、Michael C. Hewitt、Scott C. Malcolm、Fengjiang Wang、Jianguo Ma、Una C. Campbell、Nancy A. Spicer、Sharon R. Engel、Larry W. Hardy、Zhi-Dong Jiang、Rudy Schreiber、Kerry L. Spear、Mark A. Varney

  DOI：10.1021/jm101312a

  日期：2011.8.11

  The present work expands the chemical space known to offer potent inhibition of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) and discloses novel bicyclic octahydrocyclopenta[c]pyrrole and octahydro-1H-isoindole scaffolds as potent triple reuptake inhibitors (TRIs) for the potential treatment of depression. Optimized compounds 22a (SEAT, NET, DAT, IC(50) = 20, 109, 430 nM), 23a (SERT, NET, DAT, IC(50) = 29, 85, 168 nM), and 26a (SERT, NET, DAT, IC(50) = 53, 150, 140 nM) were highly brain penetrant, active in vivo in the mouse tail suspension test at 10 and 30 mpk PO, and were not generally motor stimulants at doses ranging from 1 to 30 mpk PO. Moderate in vitro cytochrome P450 (CYP) and potassium ion channel Kv11.1 (hERG) inhibition were uncovered as potential liabilities for the chemical series.
• Arylation of Unsaturated Systems by Free Radicals. VII. The Meerwein Reaction. V.¹ Further Arylations of Maleimides. Ultraviolet Spectra of Arylmaleimides, Arylmaleic Anhydrides and Arylmaleo- and Fumaronitriles
  作者：Christian S. Rondestvedt、Max J. Kalm、O. Vogl

  DOI：10.1021/ja01604a044

  日期：1956.12