cis-(E)-4-phenyl-5-styryldihydrofuran-2(3H)-one

• 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: cis-(E)-4-phenyl-5-styryldihydrofuran-2(3H)-one
• 英文别名: (±)cis-4-phenyl-5-((E)-styryl)dihydrofuran-2(3H)-one；(4R,5S)-4-phenyl-5-[(E)-2-phenylethenyl]oxolan-2-one
• 化学式: C₁₈H₁₆O₂
• 分子量: 264.324
• InChiKey: PBDDDALNOGNSBE-SFDDJJRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 sodium hydroxide 、 sodium perchlorate 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 cis-(E)-4-phenyl-5-styryldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Electrohydrodimerization of trans-cinnamaldehyde

  摘要：

  The electrochemical reduction of trans-cinnamaldehyde in protic medium (MeOH-NaClO4) on a mercury cathode gives four cyclic hydrodimeric products in 80% yield, through a ''head to tail'' coupling pathway. The different anomers were identified as (+/-)-c-4-phenyl-t-5-[(E)-styryl]tetrahydrofuran-r-2-ol, (+/-)-t-4-phenyl-t-5-[(E)-styryl]tetrahydrofuran-r-2-ol, (+/-)-c-4-phenyl-t-5-[(E)-styryl]tetrahydrofuran-r-2-ol and (+/-)-c-4-phenyl-c-5-[(E)-styryl]tetrahydrofuran-r-2-ol in a ratio of 38:32:27:3 respectively. Ethyl glycoside derivatives and lactones have been obtained from the electrosynthesized products. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00242-1

文献信息

• Catalytic Generation of Activated Carboxylates from Enals:  A Product-Determining Role for the Base
  作者：Stephanie S. Sohn、Jeffrey W. Bode

  DOI：10.1021/ol051269w

  日期：2005.9.1

  from imidazolium or triazolium salts and bases react with enals, leading to the catalytic generation of homoenolates. The fate of these intermediates is determined by the catalytic base: strong bases such as (t)BuOK lead to carbon-carbon bond formation, while weaker bases allow protonation of the homoenolate and subsequent generation of activated carboxylates. This discovery, along with the design of a

  由咪唑鎓或三唑鎓盐和碱原位生成的N-杂环碳氧烷与烯醛反应，导致催化生成均烯酸酯。这些中间体的命运取决于催化碱：强碱（如（t）BuOK）会导致碳-碳键的形成，而较弱的碱则会使均烯酸酯质子化并随后生成活化的羧酸酯。这一发现，再加上新型三唑鎓预催化剂的设计，使烯类能够进行催化，原子经济的氧化还原酯化反应。[反应：看文字]
• <i>N</i>-Heterocyclic Carbene-Catalyzed Generation of Homoenolates:  γ-Butyrolactones by Direct Annulations of Enals and Aldehydes
  作者：Stephanie S. Sohn、Evelyn L. Rosen、Jeffrey W. Bode

  DOI：10.1021/ja044714b

  日期：2004.11.1

  generation of reactive homoenolates from alpha,beta-unsaturated aldehydes. The catalyst-bound homoenolate reacts with electrophilic aldehydes leading, via the key intermediacy of an activated carboxylate, to gamma-butyrolactones in good yields and stereoselectivities. Importantly, this process demonstrates an unprecedented reaction mode for the generation of nucleophilic carbanions with a multifunctional

  由二芳基咪唑鎓盐原位制备的 N-杂环卡宾用作高效催化剂，用于从 α,β-不饱和醛生成反应性均烯醇化物。与催化剂结合的均烯醇化物与亲电子醛反应，通过活化羧酸盐的关键中间体，以良好的产率和立体选择性生成 γ-丁内酯。重要的是，该过程展示了一种前所未有的反应模式，用于在非常温和和方便的反应条件下使用多功能有机催化剂生成亲核碳负离子。
• Imidazolium chiral ionic liquid derived carbene-catalyzed conjugate umpolung for synthesis of γ-butyrolactones
  作者：Feng-Li Yu、Jia-Jia Jiang、Dong-Mei Zhao、Cong-Xia Xie、Shi-Tao Yu

  DOI：10.1039/c3ra40211h

  日期：——

  A serial of imidazolium chiral ionic liquids starting from commercially available (−)-menthol as a chiral pool have been synthesized and successfully used for catalyzing conjugate umpolung of α,β-unsaturated aldehydes to stereoselectively synthesize γ-butyrolactones. The catalytic activities of these ionic liquids are examined and compared. The reaction of trans-cinnamaldehyde and p-methoxycarbonyl benzaldehyde as a model has been investigated in detail, and the reaction conditions have been optimized. Under the selected conditions, the ionic liquid catalyst can catalyze the annulations of trans-cinnamaldehyde with different aromatic aldehydes to afford differently substituted γ-butyrolactones. The recyclability of the ionic liquid catalyst is investigated, and the results have indicated that the catalyst can be recycled six times without obvious activity decreasing.

  一系列以市售的（−）-薄荷醇作为手性源的咪唑鎓型手性离子液体已被合成，并成功用于催化α,β-不饱和醛的共轭umpolung反应，以立体选择性地合成γ-丁内酯。考察并比较了这些离子液体的催化活性。以反式肉桂醛和对甲氧羰基苯甲醛的反应为模型进行了详细研究，并优化了反应条件。在选定的条件下，离子液体催化剂能够催化反式肉桂醛与不同芳香醛的环化反应，得到不同取代的γ-丁内酯。研究了离子液体催化剂的循环使用性能，结果表明该催化剂可循环使用六次而活性无明显下降。
• Cooperative <i>N</i>-Heterocyclic Carbene/Lewis Acid Catalysis for Highly Stereoselective Annulation Reactions with Homoenolates
  作者：Benoit Cardinal-David、Dustin E. A. Raup、Karl A. Scheidt

  DOI：10.1021/ja910666n

  日期：2010.4.21

  A new approach that takes advantage of N-heterocyclic carbene/Lewis acid cooperative catalysis provides access to cis-1,3,4-trisubstituted cyclopentenes from enals and chalcone derivatives with high levels of diastereoselectivity and enantioselectivity. The presence of Ti(OiPr)(4) as the Lewis acid allows for efficient substrate preorganization, which translates into high levels of diastereoselectivity

  一种利用 N-杂环卡宾/路易斯酸协同催化的新方法可以从具有高水平非对映选择性和对映选择性的烯醛和查尔酮衍生物中获得顺式 1,3,4-三取代的环戊烯。Ti(OiPr)(4) 作为路易斯酸的存在允许有效的底物预组织，这转化为高水平的非对映选择性。此外，我们证明了通过使用催化量的手性路易斯酸作为光学活性促进剂的独特来源来控制 NHC 催化反应的绝对立体化学的可能性。
• Titanium Salen Complexes with Appended Silver NHC Groups as Nucleophilic Carbene Reservoir for Cooperative Asymmetric Lewis Acid/NHC Catalysis
  作者：Katja Latendorf、Melanie Mechler、Irina Schamne、Daniel Mack、Wolfgang Frey、René Peters

  DOI：10.1002/ejoc.201700436

  日期：2017.8.2

  Lewis acid catalysis and nucleophilic carbene catalysis are complementary fundamental concepts to accelerate and control chemical reactions of aldehyde substrates. Their efficient merger has recently been achieved using two separate catalyst species. The present report describes our efforts to develop a cooperative catalyst system which incorporates both features – Lewis acid and nucleophilic NHC –

  路易斯酸催化和亲核卡宾催化是互补的基本概念，用于加速和控制醛底物的化学反应。最近，使用两种独立的催化剂种类实现了有效的合并。本报告描述了我们在同一个催化剂实体中开发兼具两种特性（路易斯酸和亲核NHC）的协同催化剂体系的努力。为了在非常温和的条件下生成游离卡宾基团，形成了Ag-NHC络合物，并用PPh 3处理后释放出亲核卡宾。结果是形成烯醇-δ-内酯作为新的烯二聚产物。银对于反应模式是必不可少的，因此表明它在催化事件中起着双重作用。