4-Methoxy-3-phenyl-2-butenoic acid lactone | 103647-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-Methoxy-3-phenyl-2-butenoic acid lactone
• 英文别名: 3-phenyl-4-methoxy-2-butenolide；4-Hydroxy-4-methoxy-3-phenyl-buten-(2)-saeure-lacton；2-methoxy-3-phenyl-2H-furan-5-one
• CAS: 103647-10-5
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: NIRNITKZYDOQDK-UHFFFAOYSA-N

物化性质

• 熔点：
  52.2-53.0 °C(Solv: hexane (110-54-3))
• 沸点：
  135 °C(Press: 1 Torr)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methoxy-3-phenyl-2-butenoic acid lactone 、 乙烯 以 丙酮 为溶剂， 反应 8.0h， 生成 (1R,4R,5S)-4-Methoxy-5-phenyl-3-oxa-bicyclo[3.2.0]heptan-2-one 、 (1R,4S,5S)-4-Methoxy-5-phenyl-3-oxa-bicyclo[3.2.0]heptan-2-one
  参考文献：
  名称：

  Chiral induction in photochemical reactions - 15.

  摘要：

  The mechanism of the diastereoselection in the photosensitized [2 + 2]-cycloaddition reaction of ethylene to 5-alkoxy-2(5H)-furanones is investigated. The dependence of product ratio on the reaction temperature as well as on structural features of the enone system is measured. The structure dependent activation parameter differences (Delta Delta H-#, Delta Delta S-#) obtained by this method (modified Eyring plot) are used as a tool to characterize the stereoelectronic factors, which are responsible for the diastereoselection. In detail these factors involve: pyramidalization of the beta-carbon, homoanomeric effect, and the steric requirements of the alkoxy substituent in the relaxed ((3) pi pi*)-excited furanones.

  DOI：

  10.1016/s0040-4020(01)89419-9
• 作为产物：
  描述：

  3-苯基-2H-呋喃-5-酮 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 生成 4-Methoxy-3-phenyl-2-butenoic acid lactone
  参考文献：
  名称：

  通过芳烃重氮盐与2,5-二氢呋喃的Heck反应快速合成4-芳基-γ-丁内酯，-呋喃-2（5H）-和-5-烷氧基呋喃-2（5H）-

  摘要：

  描述了涉及2,5-二氢呋喃的Heck反应和随后的迭代NBS氧化反应的4-取代呋喃-2（5H）-酮的异常简单而短的合成序列。

  DOI：

  10.1016/0040-4039(96)01994-6

文献信息

• Towards the catalytic formation of α,β-vinylesters and alkoxy substituted γ-lactones
  作者：Pradeep Mathur、Raj Kumar Joshi、Badrinath Jha、Amrendra K. Singh、Shaikh M. Mobin

  DOI：10.1016/j.jorganchem.2010.08.036

  日期：2010.11

  A facile, one pot, high yield synthesis of α,β-vinylester (1–14) and alkoxy substituted γ-lactones (15–28) has been achieved by the photochemical reaction of terminal acetylene (ferrocenyl phenyl trimethylsillyl, hexyl and cyclohexyl) with alcohol (methanol, ethanol and isopropanol) and carbon monoxide in presence of iron pentacarbonyl as a catalyst. The selectivity of the compounds depends on the

  一种简便，一锅，α，β-乙烯基酯（的高收率合成1 - 14）和烷氧基取代的γ内酯（15 - 28）已经由终端乙炔的光化学反应来实现（二茂铁基苯基trimethylsillyl，己基和环己基）在五羰基铁的催化作用下，用醇（甲醇，乙醇和异丙醇）和一氧化碳制得。化合物的选择性取决于反应的光解时间以及所用的溶剂。分离出稳定的反应中间体铁，并用醇进一步光解，导致形成α，β-乙烯基酯。所有化合物均已通过光谱法和化合物1的分子结构进行了充分表征，16，17和20进行了结晶学确定。
• Reactions of Dichlorocyclobutenones with nucleophiles: A Synthesis of Some New Cyclobutenones and an Unusual Ring Expansion to a Butenolide
  作者：John L. Dillon、Qi Gao

  DOI：10.1021/jo00101a062

  日期：1994.11
• Dillon John L., Gao Qi, J. Org. Chem, 59 (1994) N 22, S 6868-6870
  作者：Dillon John L., Gao Qi

  DOI：——

  日期：——
• An expeditious synthesis of 4-aryl-γ-butyrolactones, -furan-2(5H)-ones and -5-alkoxyfuran-2(5H)-ones via Heck-reaction of arenediazonium salts with 2,5-dihydrofuran
  作者：Goverdhan Mehia、Saunitra Sengupta

  DOI：10.1016/0040-4039(96)01994-6

  日期：1996.11

  An exceptionally simple and short synthetic sequence to 4-substituted furan-2(5H)-ones involving a Heck reaction on 2,5-dihydrofuran and subsequent iterative NBS oxidation is described.

  描述了涉及2,5-二氢呋喃的Heck反应和随后的迭代NBS氧化反应的4-取代呋喃-2（5H）-酮的异常简单而短的合成序列。
• Chiral induction in photochemical reactions - 15.
  作者：Norbert Hoffmann、Helmut Buschmann、Gerhard Raabe、Hans-Dieter Scharf

  DOI：10.1016/s0040-4020(01)89419-9

  日期：1994.1

  The mechanism of the diastereoselection in the photosensitized [2 + 2]-cycloaddition reaction of ethylene to 5-alkoxy-2(5H)-furanones is investigated. The dependence of product ratio on the reaction temperature as well as on structural features of the enone system is measured. The structure dependent activation parameter differences (Delta Delta H-#, Delta Delta S-#) obtained by this method (modified Eyring plot) are used as a tool to characterize the stereoelectronic factors, which are responsible for the diastereoselection. In detail these factors involve: pyramidalization of the beta-carbon, homoanomeric effect, and the steric requirements of the alkoxy substituent in the relaxed ((3) pi pi*)-excited furanones.