(5Z)-5-[(E)-3-phenylallylidene]-5H-furan-2-one | 158071-58-0

• 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: (5Z)-5-[(E)-3-phenylallylidene]-5H-furan-2-one
• 英文别名: (Z)-5-((E)-3-phenylallylidene)furan-2(5H)-one；(5Z)-5-cinnamylidene-furan-2-one；(5Z)-5-[(E)-3-phenylprop-2-enylidene]furan-2-one
• CAS: 158071-58-0
• 化学式: C₁₃H₁₀O₂
• 分子量: 198.221
• InChiKey: GCTNFTCLESDOLV-JHLWKMQHSA-N

物化性质

• 沸点：
  392.8±31.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (5Z)-5-[(E)-3-phenylallylidene]-5H-furan-2-one 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 hydroquinine 1,4-phthalazinediyl diether 、 三正丁基氢锡 、 碳酸氢钠 作用下， 以 甲苯 为溶剂， 反应 72.42h， 生成 8-epi-crassalactone D
  参考文献：
  名称：

  Galan-Fernandez, Raquel; Clemente-Tejeda, David; Bermejo, Francisco A., ARKIVOC, 2012, vol. 2012, # 9, p. 1 - 14

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-cinnamaldehyde dimethylacetal 在 potassium acetate 、 四氯化钛 作用下， 以 溶剂黄146 为溶剂， 生成 (5Z)-5-[(E)-3-phenylallylidene]-5H-furan-2-one
  参考文献：
  名称：

  Synthesis and stereochemical assignments for goniobutenolides A and B

  摘要：

  Goniobutenolides A and B and their C-7 epimers are stereoselectively synthesized using osmium-catalyzed asymmetric dihydroxylation (AD) as the key transformation. The relative and absolute stereochemistry gf the natural goniobutenolides A and B are assigned with reference to the spectral data and optical rotations from the literature.

  DOI：

  10.1016/s0040-4039(00)76941-3

文献信息

• Ring-Closing Metathesis Reactions of Acyloxysulfones: Synthesis of γ-Alkylidene Butenolides
  作者：Gregory O’Neil、Iris Phan、Garrett Gilbert

  DOI：10.1055/s-0034-1378721

  日期：——

  An acyloxysulfone ring-closing metathesis/sulfone elimination sequence has been developed for the preparation of various γ-alkylidene butenolides. The elimination is proposed to proceed via an E1cb mechanism leading to (Z)-γ-alkylidene butenolides as the major products.

  已经开发了一种酰氧基砜闭环复分解/砜消除序列，用于制备各种 γ-亚烷基丁烯内酯。建议通过 E1cb 机制进行消除，导致 (Z)-γ-亚烷基丁烯内酯作为主要产物。
• Regioselective Synthesis of (E)-5-(Tributylstannylmethylidene)-5H-furan-2-ones and (E)-3-(Tributylstannylmethylidene)-3H-isobenzofuran-1-ones: Easy Access to γ-Alkylidenebutenolide and Phthalide Skeletons
  作者：Mohamed Abarbri、Alain Duchêne、Jérôme Thibonnet、Jean-Luc Parrain、Elsa Anselmi

  DOI：10.1055/s-2007-965890

  日期：2007.2

  Regio- and stereoselective synthesis of γ-alkylidene­butenolides and γ-alkylidenephthalides has been achieved through the palladium-catalysed tandem cross-coupling/cyclisation reactions of tributylstannyl-3-iodopropenoate or the 2-iodo benzoate derivatives with tributyltinacetylene. Iododestannylation occurred with inversion of the configuration of the exocyclic double bond in the case of butenolides, but with retention of configuration for the phthalide. The selectivity observed in the Stille reaction was found to be dependent on the nature of the vinyl or the aryl halide.

  已通过钯催化的串联交叉耦合/环化反应合成了γ-烷基烯烃内酯和γ-烷基烯酰内酯，反应底物为三丁基锡-3-碘丙烯酸酯或2-碘苯甲酸酯衍生物与三丁基锡炔的反应。在烯酮内酯的情况下，碘去锡反应发生了外环双键构型的反转，而在酞内酯中则保持构型。观察到的斯蒂尔反应选择性与乙烯基或芳基卤化物的性质有关。
• A Novel Access to γ-Alkylidenebutenolides: Sequential Stille Couplings of Dibromomethylenebutenolides
  作者：Reinhard Brückner、Achim Sorg、Konrad Siegel

  DOI：10.1055/s-2003-44997

  日期：——

  γ-(Dibromomethylene)butenolide (2) and β-bromo-γ-(bromomethylene)butenolide (Z-5), both of which obtained from dibromolevulinic acid (6) in a single step, underwent Pd-catalyzed couplings with phenyl- or styryltributylstannane giving mono­bromobutenolides with excellent stereo- and regiocontrol. A second Stille coupling or the reduction with Zn dust led to bromine-free γ-alkylidenebutenolides as single stereoisomers.

  δ-（二溴亚甲基）丁烯内酯（2）和δ-²-溴-δ-（溴亚甲基）丁烯内酯（Z-5）均由二溴乙酰丙酸（6）一步制得，它们在 Pd 催化下与苯基或苯乙烯基三丁基锡烷发生偶联反应，得到具有极佳立体和区域控制的单溴丁烯内酯。通过第二次 Stille 偶联或与 Zn 粉尘的还原反应，可得到不含溴的δ-亚烷基丁烯酸单立体异构体。
• Galan-Fernandez, Raquel; Clemente-Tejeda, David; Bermejo, Francisco A., ARKIVOC, 2012, vol. 2012, # 9, p. 1 - 14
  作者：Galan-Fernandez, Raquel、Clemente-Tejeda, David、Bermejo, Francisco A.

  DOI：——

  日期：——
• Synthesis and stereochemical assignments for goniobutenolides A and B
  作者：Daqiang Xu、K. Barry Sharpless

  DOI：10.1016/s0040-4039(00)76941-3

  日期：1994.7

  Goniobutenolides A and B and their C-7 epimers are stereoselectively synthesized using osmium-catalyzed asymmetric dihydroxylation (AD) as the key transformation. The relative and absolute stereochemistry gf the natural goniobutenolides A and B are assigned with reference to the spectral data and optical rotations from the literature.