(E)-5-styryltetrahydrofuran-2(3H)-one | 119702-51-1

• 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: (E)-5-styryltetrahydrofuran-2(3H)-one
• 英文别名: (E)-5-styryldihydrofuran-2(3H)-one；(E)-4-styrylbutanolide；5-[(E)-2-phenylethenyl]oxolan-2-one
• CAS: 119702-51-1
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: NIJXYOQCZNHOAX-VOTSOKGWSA-N

物化性质

• 沸点：
  357.9±31.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-5-styryltetrahydrofuran-2(3H)-one 在 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 potassium ferricyanide 、 水 、 碳酸氢钠 、 potassium carbonate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 (R)-5-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A C–H oxidation approach for streamlining synthesis of chiral polyoxygenated motifs

  摘要：

  Chiral oxygenated molecules are pervasive in natural products and medicinal agents; however, their chemical syntheses often necessitate numerous, wasteful steps involving functional group and oxidation state manipulations. Herein a strategy for synthesizing a readily diversifiable class of chiral building blocks, allylic alcohols, through sequential asymmetric C H activation/resolution is evaluated against the state-of-the-art. The C H oxidation routes' capacity to strategically introduce oxygen into a sequence and thereby minimize non-productive manipulations is demonstrated to effect significant decreases in overall step-count and increases in yield and synthetic flexibility. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.012
• 作为产物：
  描述：

  6-phenylhex-5-ynoic acid 在 四(三苯基膦)钯 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以80%的产率得到(E)-5-styryltetrahydrofuran-2(3H)-one
  参考文献：
  名称：

  炔烃分子内加氢羧化反应中β-氢化物消除的抑制导致内酯的形成

  摘要：

  研究了钯催化的炔酸分子内环化反应，得到中等价位的五元和六元内酯。该反应可以简单地通过在催化量的Pd（PPh 3）4和（o- tol）3 P存在下于100°C加热炔酸的甲苯溶液进行。该转化的关键是使用膦代替羧酸作为添加剂。与我们先前开发的催化体系相似，使用羧酸代替（邻甲苯基）3 P导致了二烯的排他性形成。

  DOI：

  10.1002/adsc.200600507

文献信息

• Design, synthesis, in vitro cytotoxicity evaluation and structure–activity relationship of Goniothalamin analogs
  作者：Mazlin Mohideen、Suraya Zulkepli、Nik-Salmah Nik-Salleh、Mohd Zulkefeli、Jean-Frédéric Faizal Abdullah Weber、A. F. M. Motiur Rahman

  DOI：10.1007/s12272-013-0099-1

  日期：2013.7

  A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5-(hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC50 = 12 μM). Structure–activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.

  一系列六/五元（E/Z）-钩藤烷类似物从商业可得的（3,4-二氢-2H-吡喃-2-基）甲醇/5-（羟甲基）二氢呋喃-2（3H）-酮在三步反应中被合成，总产率良好至中等，并对它们对淋巴母细胞性白血病T细胞系（Jurkat E6.1）的细胞毒性进行了评估。在合成的类似物中，（Z）-钩藤烷显示出最高的细胞毒性活性（IC50 = 12 μM）。构效关系研究表明，在苯环中引入取代基或用吡啶/萘替换苯环，或者减小内酯环的大小（从六元到五元）并不会增加细胞毒性。
• Synthesis of vinylic lactones via palladium-catalyzed coupling of vinylic halides or triflates and unsaturated carboxylic acids
  作者：Richard C. Larock、David J. Leuck、L.Wayne Harrison

  DOI：10.1016/s0040-4039(00)82356-4

  日期：1988.1

  Vinylic halides or triflates react with 3-butenoic or 4-pentenoic acids in the presence of 5% Pd(OAc)2 or Pd(dba)2, -Bu4NCl, -PrNEt2 and either acetonitrile or ,-dimethylformamide at 80–100°C to afford the corresponding γ-alkenyl-γ-butyro- or δ-alkenyl-δ-valerolactones respectively by an intramolecular π-allylpalladium displacement process.

  乙烯基卤化物或三氟甲磺酸酯与反应3-丁或在5％的Pd（OAC）存在下4-戊烯酸2或Pd（DBA）2，-Bu 4的NCI，-PrNEt 2和乙腈或，二甲基甲酰胺在80〜在100℃下通过分子内π-烯丙基钯置换工艺分别得到相应的γ-烯基-γ-丁酰基-或δ-烯基-δ-戊内酯。
• γ-Substituted Butanolides from Cyclopropane Hemimalonates: An Expedient Synthesis of Natural (<i>R</i>)-Dodecan-4-olide
  作者：Huck K. Grover、Michael R. Emmett、Michael A. Kerr

  DOI：10.1021/ol402252u

  日期：2013.9.20

  hemimalonates has led to the facile synthesis of γ-substituted butanolides. Under microwave irradiation, cyclopropane hemimalonates undergo rapid conversion to butanolides in the presence of inorganic salts with an unprecedented retention of stereochemistry. This unique process has been applied to the total synthesis of the naturally occurring (R)-dodecan-4-olide.

  对供体-受体环丙烷半棉酸酯的反应性的探索导致了γ-取代丁醇化物的简便合成。在微波辐射下，在无机盐的存在下，环丙烷半棉酸酯迅速转化为丁醇化物，并保持了前所未有的立体化学。该独特的方法已应用于天然存在的（R）-dodecan-4-olide的全合成。
• Divergent Synthetic Routes for Ring Expansion or Cyclization from 1,4-Allylic Diol Derivatives via Gold(I) Catalysis or Zinc(II) Mediation
  作者：Li−Li Zhu、Xiao-Xiao Li、Wen Zhou、Xin Li、Zili Chen

  DOI：10.1021/jo2015517

  日期：2011.11.4

  rearrangement, provided a new strategy to synthesize five-carbon homologated ring ketones. In addition, using ZnBr2, 2,5-dihydrofuran products were obtained in moderate to good yields via an intramolecular cyclization process.

  开发了一种新的有效方法，通过金催化的烯丙基阳离子促进的频哪醇型重排，使用各种酯作为离去基团，将环状链烷醇转化为一碳高级同源酮。该反应，加上oxy-Cope重排，为合成五碳均聚物环酮提供了新的策略。另外，使用ZnBr 2，通过分子内环化过程以中等至良好的产率获得了2，5-二氢呋喃产物。
• Mercury in organic chemistry. 35. Synthesis of vinylic lactones from vinylmercurials and alkenoic acids via intramolecular π-allylpalladium displacement
  作者：Richard C. Larock、David J. Leuck、L.Wayne Harrison

  DOI：10.1016/s0040-4039(00)96674-7

  日期：1987.1

  Li2PdCl4 and 3-butenoic or 4-pentenoic acids, followed by refluxing with K2CO3, affords high yields of the corresponding γ-alkenyl-γ-butyro- or δ-alkenyl-δ-valerolactones by an intramolecular π-allylpalladium displacement process.

  乙烯基汞氯化物，Li 2 PdCl 4和3-丁烯酸或4-戊烯酸的反应，然后与K 2 CO 3回流，得到相应的γ-烯基-γ-丁丁-或δ-烯基-δ-的高产率。戊内酯通过分子内π-烯丙基钯置换工艺制备。