(Z)-3-(4-methoxybenzylidene)dihydro-2(3H)-furanone | 1530-62-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-3-(4-methoxybenzylidene)dihydro-2(3H)-furanone
• 英文别名: (E)-3-(4-methoxybenzylidene)dihydrofuran-2(3H)-one；NSC 10428；3-[(Z)-4-Methoxybenzylidene]oxolane-2-one；(3Z)-3-[(4-methoxyphenyl)methylidene]oxolan-2-one
• CAS: 1530-62-7
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: MBSKMEQHKIKWQZ-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲烯基丁内酯 、 4-碘苯甲醚 在 palladium diacetate potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以52%的产率得到(Z)-3-(4-methoxybenzylidene)dihydro-2(3H)-furanone
  参考文献：
  名称：

  Palladium-Catalysed Vinylic Substitution of Aryl/Vinyl Iodides and Triflates with α-Methylene-γ-butyrolactone − An Application to the Synthesis of 3-Alkyl-γ-Butyrolactones through Combined Palladium-Catalysed Coupling/Hydrogenation Reactions

  摘要：

  DOI：

  10.1002/1099-0690(200108)2001:16<3165::aid-ejoc3165>3.0.co;2-6

文献信息

• Systematic Investigation into the Matsuda–Heck Reaction of α-Methylene Lactones: How Conformational Constraints Direct the β-H-Elimination Step
  作者：Bernd Schmidt、Felix Wolf、Christopher Ehlert

  DOI：10.1021/acs.joc.6b02207

  日期：2016.11.18

  were correlated with the dihedral angles between Pd and endo-β-H. This correlation revealed that in the case of the six-membered lactone an energetically favorable conformer adopts a nearly synperiplanar Pd/endo-β-H arrangement, whereas for the analogous Pd σ-complex of the five-membered lactone the smallest Pd/endo-β-H dihedral angle is observed for a conformer with a comparatively high potential energy

  α-亚甲基-γ-丁内酯和α-亚甲基-δ-戊内酯与芳烃重氮盐在Pd催化的Matsuda-Heck偶联作用下分别与α-苄基丁烯化物或戊烯醇化物或与α-苄基内酯结合。观察到的区域选择性强烈依赖于环的大小，六元环仅产生α-苄基戊烯醚化物，而五元α-亚甲基内酯与具有高比例（E）-α-亚苄基-γ-的区域异构体混合物反应丁内酯。DFT计算表明，这些差异的原因不是热力学而是动力学性质。插入Pd-芳基键所产生的Pdσ-复合物构象的相对能量与Pd和内在分子之间的二面角相关-β-H。这种相关性表明，在六元内酯的情况下，在能量上有利的构象异构体采用接近同平面的Pd /内-β-H排列，而对于五元内酯的类似Pdσ-复合物，最小的Pd /内-对于具有相对高的势能的构象异构体，观察到β-H二面角。exo-亚甲基内酯的Matsuda-Heck芳基化反应的优化条件最终被用于天然产物anemarcoumarin A的合成。
• 3-(Arylmethyl)-1-(3'-diethylaminopropyl) pyrrolidines and process of preparation thereof
  申请人：Council of Scientific and Industrial Research

  公开号：EP0562185A1

  公开（公告）日：1993-09-29

  The novel compounds 3-(arylmethyl)-1-(3'-diethylaminopropyl) pyrrolidines are disclosed which have the general formula: wherein R represents an alkoxy group having 1 to 6 carbon atoms, like methoxy, ethoxy, propoxy or butoxy and a process for preparing the same. Particularly, the invention provides the compound having the above said formula wherein the alkoxy substituent is in the 4 position of the benzene ring or the substituent methylenedioxy at 3 and 4 position. The compounds have the property of reversing the resistance of chloroquine resistant strains of the malarial parasite P. berghi in vivo and P. falciparum in vitro and can be used for reversing the resistance of human malarial parasites, particularly P. falciparum. The invention also includes compositions containing the new compounds and an anti-malarial drug, preferably chloroquine.

  本发明揭示了一种新型化合物3-(芳基甲基)-1-(3'-二乙基氨基丙基)吡咯烷，其具有以下通式： 其中R代表1至6个碳原子的烷氧基，例如甲氧基、乙氧基、丙氧基或丁氧基，并提供一种制备该化合物的方法。特别地，本发明提供了上述通式中烷氧基取代基位于苯环的4位或取代基为3和4位的亚甲二氧基。该化合物具有在体内逆转氯喹耐药性疟原虫P. berghi和体外逆转P. falciparum的特性，并可用于逆转人类疟原虫，特别是P. falciparum的耐药性。本发明还包括含有新化合物和抗疟药物（优选为氯喹）的组合物。
• Palladium-Catalyzed Arylation of α-Methylene-γ-butyrolactone:  3-Benzylfuran-2(5<i>H</i>)-ones vs (<i>Z</i>)-Benzylidene-γ-butyrolactones and Their Reduction to 3-Benzyl-γ-butyrolactones
  作者：Antonio Arcadi、Marco Chiarini、Fabio Marinelli、Zoltán Berente、Làszlò Kollàr

  DOI：10.1021/ol9912130

  日期：2000.1.1

  [GRAPHICS]The palladium-catalyzed arylation of the alpha-methylene-gamma-butyrolactone proceeds in good yields and may be directed toward the synthesis of 3-benzylfuran-2(5H)-ones when the starting aryl iodides contain strongly electron withdrawing groups. The combined palladium-catalyzed arylation/hydrogenation of the alpha-methylene-gamma-butyrolactone represents a new simple entry into functionalized alpha-benzyl-gamma-butyrolactones.
• Verwendung von verätherten 2-(4-Hydroxybenzyliden)-gamma-butyrolactonen als Lichtschutzmittel
  申请人：BASF Aktiengesellschaft

  公开号：EP0044970B1

  公开（公告）日：1983-06-22