methyl 2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate | 134391-10-9

• 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: methyl 2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate
• 英文别名: Methyl 5-methyl-2-phenyl-2,3-dihydrofuran-4-carboxylate
• CAS: 134391-10-9
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: UVCUVSNXJNJQRN-UHFFFAOYSA-N

物化性质

• 沸点：
  308.1±42.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate 在 3,4,5-三甲基苯酚 、 scandium tris(trifluoromethanesulfonate) 作用下， 反应 6.0h， 以99%的产率得到1-甲基-2-萘甲酸甲酯
  参考文献：
  名称：

  3,4,5-三甲基苯酚和路易斯酸双催化级联开环/环化反应：萘的直接合成

  摘要：

  通过开环和环化反应，开发了一种3,4,5-三甲基苯酚和路易斯酸双重催化的供体-受体（DA）环丙烷级联反应。在该反应中，酚类化合物首次被用作共价催化剂。另外，对照实验证明3,4,5-三甲基苯酚通过完成C–C键断裂而完成了催化循环。使用这种策略，在温和条件下，由D–A环丙烷以中等到高收率合成了各种各样的取代萘。

  DOI：

  10.1021/acs.orglett.7b03392
• 作为产物：
  描述：

  methyl 1-acetyl-2-phenylcyclopropanecarboxylate 在 scandium tris(trifluoromethanesulfonate) 作用下， 反应 48.0h， 生成 methyl 2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate
  参考文献：
  名称：

  3,4,5-三甲基苯酚和路易斯酸双催化级联开环/环化反应：萘的直接合成

  摘要：

  通过开环和环化反应，开发了一种3,4,5-三甲基苯酚和路易斯酸双重催化的供体-受体（DA）环丙烷级联反应。在该反应中，酚类化合物首次被用作共价催化剂。另外，对照实验证明3,4,5-三甲基苯酚通过完成C–C键断裂而完成了催化循环。使用这种策略，在温和条件下，由D–A环丙烷以中等到高收率合成了各种各样的取代萘。

  DOI：

  10.1021/acs.orglett.7b03392

文献信息

• Cooperative Indium(III)/Silver(I) System for Oxidative Coupling/Annulation of 1,3-Dicarbonyls and Styrenes: Construction of Five-Membered Heterocycles
  作者：Tae Yun Ko、So Won Youn

  DOI：10.1002/adsc.201600280

  日期：2016.6.16

  A cooperative indium(III)/silver(I) system for the synthesis of various five‐membered heterocycles, including dihydrofurans, pyrroles, spirolactones, and spiroiminolactones, through the sequential oxidative coupling/annulation reaction of 1,3‐dicarbonyl compounds with styrenes has been developed. Four different heterocyclic systems were successfully synthesized depending on the substitution pattern

  通过1,3-二羰基化合物与苯乙烯的顺序氧化偶合/环化反应，用于合成五元杂环（包括二氢呋喃，吡咯，螺内酯和螺氨基内酯）的铟（III）/银（I）协作系统具有已开发。使用容易获得的起始材料，根据底物的取代方式成功合成了四个不同的杂环系统。该系统的优点是底物范围广，化学产率中等到良好，操作上简单易行，反应时间短。
• Chemodivergent Photocatalytic Synthesis of Dihydrofurans and β,γ‐Unsaturated Ketones
  作者：Arianna Quintavalla、Ruben Veronesi、Davide Carboni、Ada Martinelli、Nelsi Zaccheroni、Liviana Mummolo、Marco Lombardo

  DOI：10.1002/adsc.202100260

  日期：2021.7

  A synthetic procedure, catalysed by Ir(ppy)3 under visible-light irradiation, for the chemodivergent synthesis of 2,3-dihydrofurans (3) or β,γ-unsaturated ketones (7) starting from α-halo ketones (1) and alkenes (2) has been developed. The mild reaction conditions and the redox-neutral nature of the process make it particularly sustainable avoiding the use of both sacrificial reactants and stoichiometric

  在可见光照射下由 Ir(ppy) 3催化的合成方法，用于从 α-卤代酮 ( 1 ) 和2,3-二氢呋喃 ( 3 ) 或 β,γ-不饱和酮 ( 7 )化学发散合成烯烃 ( 2 ) 已被开发。该过程的温和反应条件和氧化还原中性性质使其特别可持续，避免使用牺牲反应物和化学计量强氧化剂。在 DFT 计算的支持下，仔细的实验​​研究允许详细披露可能的机制途径，并将合成化学趋向于3或7，不仅取决于基材的性质，还取决于实验条件的选择。
• Non-decarbonylative photochemical versus thermal activation of Bu₄N[Fe(CO)₃(NO)] – the Fe-catalyzed Cloke–Wilson rearrangement of vinyl and arylcyclopropanes
  作者：Che-Hung Lin、Dominik Pursley、Johannes E. M. N. Klein、Johannes Teske、Jennifer A. Allen、Fabian Rami、Andreas Köhn、Bernd Plietker

  DOI：10.1039/c5sc02342d

  日期：——

  The base metal complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the rearrangement of vinyl and arylcyclopropanes both under thermal or photochemical conditions to give the corresponding vinyl or aryldihydrofuranes in good to excellent...

  贱金属配合物 Bu4N[Fe(CO)3(NO)] (TBA[Fe]) 在热或光化学条件下催化乙烯基和芳基环丙烷的重排，以良好至优异的性能生成相应的乙烯基或芳基二氢呋喃。
• Chalcogen Bonding Catalysis of the Cloke‐Wilson Rearrangement
  作者：Xinglong Yuan、Lintao Bao、Zhiguo Zhao、Yao Wang

  DOI：10.1002/chem.202203822

  日期：——

  Conventionally, the Cloke-Wilson rearrangement is facilitated by strong Lewis acids, Brønsted acids and Lewis bases. Herein, a chalcogen bonding catalysis approach to the Cloke-Wilson rearrangement is established, affording dihydrofurans with moderate to good yields.

  通常，强路易斯酸、布朗斯台德酸和路易斯碱会促进 Cloke-Wilson 重排。在此，建立了 Cloke-Wilson 重排的硫属键合催化方法，提供中等至良好产率的二氢呋喃。
• Electronic and steric effects in the addition of electrophilic 1,3-dicarbonylalkyl radicals to styrenes
  作者：Enrico Baciocchi、Renzo Ruzziconi

  DOI：10.1021/jo00015a037

  日期：1991.7

  The addition reactions of 1,3-dicarbonylalkyl radicals to ring-substituted styrenes have been kinetically investigated in MeOH and/or MeCN. It has been observed that the rate effect of ring substituents is nearly identical in the reactions of MeCOCHCOMe (1), MeOCOCHCOMe (2) and MeOCOCHCOOMe (4), the rho-value, in MeOH being -0.96, -1.01 and -1.06, respectively. Since the three radicals are relatively strong oxidants and have similar reduction potentials, an important contribution of the charge transfer structure RCOCHCORCH2CHAr.+ to the addition transition state is suggested. It has also be found that in the reactions of 1 and 4 with alpha-alkyl-substituted styrenes the rate of addition is strongly influenced by the nature of the alkyl group, decreasing in the order: Me > Et > (i)Pr > (t)Bu. The observed effects are much larger than those reported for the corresponding reactions of the nucleophilic cyclohexyl radical. It is suggested that the alpha-alkyl substituents exert an effect of steric inhibition of resonance thereby ring delocalization of the charge and/or unpaired electron in the transition state is significantly reduced. Delocalization may be more important in the reactions of 1 and 4 than in those of the cyclohexyl radical since it is possible that the former utilizes a transition state occurring later along the reaction coordinate and/or characterized by a larger extent of charge transfer.