(Z)-3-pentylideneisobenzofuran-1(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: (Z)-3-pentylideneisobenzofuran-1(3H)-one
• 英文别名: 1(3H)-Isobenzofuranone, 3-pentylidene-；(3Z)-3-pentylidene-2-benzofuran-1-one
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: UYKZUWVXNVHOGQ-XFXZXTDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-3-pentylideneisobenzofuran-1(3H)-one 在 C₃₈H₄₈IrNOP⁽¹⁺⁾*C₃₂H₁₂BF₂₄^(1-) 、 氢气 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、1.01 MPa 条件下， 反应 24.0h， 以95%的产率得到(R)-3-pentylbenzo[c]furan-1(3H)-one
  参考文献：
  名称：

  Ir-SpinPHOX催化3-亚萘二甲酸酯的对映选择性加氢

  摘要：

  使用基于螺[4,4] -1,6-壬二烯的膦-恶唑啉配体（SpinPHOX）的Ir I络合物作为催化剂开发了3种亚萘二甲酸酯的第一个不对称氢化反应，提供了多种手性3出色的对映体过量（最高ee达98％）的预取代邻苯二甲酸酯。该协议的实用性已在手性药物NBP和BZP前体以及天然产物创心酚和邻苯二甲酰亚胺的不对称合成中得到证明。

  DOI：

  10.1002/anie.201807639
• 作为产物：
  描述：

  3-Hydroxy-3-pentyl-2-benzofuran-1-one 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 1.5h， 生成 (Z)-3-pentylideneisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Synthesis, resolution, and antiplatelet activity of 3-substituted 1(3H)-isobenzofuranone

  摘要：

  A series of 3-substituted-1(3H)-isobenzofuranone 6a-g and 7a-g were synthesized from phthalic anhydride. The compound 6a-g was resolved. The antiplatelet activities of these compounds were evaluated using in vitro experiment of platelet aggregation. The levels of antiplatelet activity were displayed as following sequence: l-isomer > dl-isomer > d-isomer, respectively. The alkylphthalide is more active than the corresponding alkenephthalide. All these compounds were less active than n-butylphthalide (NBP, 6c) and Aspirin (Asp). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.082

文献信息

• Divergent Syntheses of (<i>Z</i>)-3-Alkylideneisobenzofuran-1(3<i>H</i>)-ones and 1<i>H</i>-Isochromen-1-ones by Copper-Catalyzed Cycloisomerization of 2-Alkynylbenzoic Acids in Ionic Liquids
  作者：Raffaella Mancuso、Christian S. Pomelli、Piera Chiappetta、Katia F. Gioia、Asif Maner、Nadia Marino、Lucia Veltri、Cinzia Chiappe、Bartolo Gabriele

  DOI：10.1021/acs.joc.8b00923

  日期：2018.6.15

  The cycloisomerization of readily available 2-alkynylbenzoic acids 1 in ionic liquids (ILs) as recyclable reaction media has been studied under the catalytic action of CuCl2. With substrates bearing an aryl group on the triple bond, a mixture of (Z)-3-alkylideneisobenzofuran-1(3H)-ones (from 5-exo-dig cyclization) and 1H-isochromen-1-ones (from 6-endo-dig cyclization) was observed in 1-ethyl-3-methylimidazolium

  在CuCl 2的催化作用下，已经研究了易得的2-炔基苯甲酸1在离子液体（ILs）中作为可循环反应介质的环异构化。在具有在三键上带有芳基的底物的情况下，（Z）-3-亚烷基亚异苯并呋喃-1（3 H）-ones（来自5 exo - dig环化反应）和1 H -isochromen-1-ones（来自6 -内型-挖环化）的1-乙基-3-甲基咪唑鎓乙基硫酸盐（EmimEtSO观察到4），同时将反应原来是仅朝向使用异苯并呋喃酮的形成选择性ñ乙基N-甲基吗啉二氰胺[Mor 1,2 N（CN）2 ]作为溶剂。当在EmimEtSO 4或Mor 1,2 N（CN）2中使用带有末端三键的底物时，也有选择地获得了5元产物。另一方面，在EmimEtSO 4中，三键上带有烷基或烯基的2-炔基苯甲酸选择性地导致1 H -isochromen-1- one ，而在Mor 1中观察到区域异构混合物的形成。2 N（CN）2。
• NHC-Catalyzed Oxidative Cyclization Reactions of 2-Alkynylbenzaldehydes under Aerobic Conditions: Synthesis of O-Heterocycles
  作者：Jong Hyub Park、Sachin V. Bhilare、So Won Youn

  DOI：10.1021/ol200481u

  日期：2011.5.6

  An NHC-catalyzed, regio- and stereoselective oxidative cyclization of o-alkynylbenzaldehydes bearing an unactivated alkyne moiety as an internal electrophile has been developed to afford phthalides and isocoumarins. A single organocatalytic system enabled two sequential C−O bond formations to take place in an atom economical manner via highly efficient dual activation. Molecular oxygen in air could

  已开发出具有NHC催化，带有未活化炔烃部分的邻炔基苯甲醛作为内部亲电子试剂的区域和立体选择性氧化环化反应，以提供邻苯二甲酸酯和异香豆素。单一的有机催化系统通过高效的双重活化，以原子经济的方式使两个连续的C-O键形成成为可能。在我们新开发的试剂系统下，空气中的分子氧可以用作氧原子的来源，用于将醛氧化为相应的苯甲酸。
• 1-Phenyl-1,2-benziodoxol-3-(1<i>H</i> )-one as Synthon for Phthalide Synthesis through Pd-Free, Base-Free, Sonogashira-Type Coupling Cyclization Reaction
  作者：Ahmad A. Almasalma、Esteban Mejía

  DOI：10.1002/ejoc.201700940

  日期：2018.1.17

  heterocycles have found broad application as atom-transfer reagents for organic synthesis. Among them, 1-Phenyl-1,2-benziodoxol-3-(1H)-one is known as a traditional benzyne precursor, but no further synthetic applications have been reported. Herein, we report the first synthetic application of 1-phenylbenzidoxole to the synthesis of Phthalides using only CuI as catalyst. High selectivity and yield were achieved

  高价碘 (III) 五元杂环已被广泛用作有机合成的原子转移试剂。其中，1-Phenyl-1,2-benziodoxol-3-(1H)-one 被称为传统的苄前体，但没有进一步的合成应用报道。在此，我们报告了仅使用 CuI 作为催化剂的 1-苯基苯并氧杂环戊烷在邻苯二甲酸酯合成中的首次合成应用。在温和的反应条件下实现了高选择性和高产率，并具有良好的官能团耐受性。在我们的研究过程中，研究了不同反应条件下不同 CuI 和 CuII 催化剂的效率。离去基团的性质、底物上的取代基和温度对产率和选择性都起着重要作用。而且，
• Copper-Catalyzed Preparation of γ-Alkylidenebutenolides and Isocoumarins under Mild Palladium-Free Conditions
  作者：Samuel Inack-Ngi、Raphaël Rahmani、Laurent Commeiras、Gaëlle Chouraqui、Jérôme Thibonnet、Alain Duchêne、Mohamed Abarbri、Jean-Luc Parrain

  DOI：10.1002/adsc.200800757

  日期：2009.3

  Abstractmagnified imageA general and efficient copper(I)‐catalyzed cross‐coupling and heterocyclization reaction of terminal alkynes and β‐iodo‐α,β‐unsaturated acid derivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5‐ylidenebutenolides and 3‐substituted isocoumarins with excellent regio‐ and stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium‐free.
• Pd/C-mediated synthesis of (Z)-3-alkylidenephthalides of potential pharmacological interest
  作者：D. Rambabu、G. Pavan Kumar、Barange Deepak Kumar、Ravikumar Kapavarapu、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2013.03.121

  日期：2013.6

  The coupling of o-bromobenzoic acid with terminal alkynes using 10% Pd/C-Et3N-CuI-PPh3 as a catalyst system leads to the synthesis of (Z)-3-alkylidenephthalides as the major product along with the traces of isocoumarin when the reaction was performed in 1,4-dioxane. The methodology afforded a range of compounds including (Z)-3-(4-(methylsulfonyl)benzylidene)isobenzofuran-1(3H)-one of potential pharmacological interest. (C) 2013 Elsevier Ltd. All rights reserved.