5-ethyl-3,4-dimethyl-2(5H)-furanone | 79379-60-5

• 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: 5-ethyl-3,4-dimethyl-2(5H)-furanone
• 英文别名: 5-Ethyl-3,4-dimethylfuran-2(5H)-one；2-ethyl-3,4-dimethyl-2H-furan-5-one
• CAS: 79379-60-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: HVQFSDFJEPPHCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  3-trimethylsilyloxy-2-pentene 在 盐酸 、 三氯化铝 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 6.25h， 生成 5-ethyl-3,4-dimethyl-2(5H)-furanone
  参考文献：
  名称：

  Novel and efficient synthesis of 2(5H)-furanone derivatives

  摘要：

  DOI：

  10.1021/jo00242a043

文献信息

• RHODIUM CARBONYL-CATALYZED CARBONYLATION OF ACETYLENES IN THE PRESENCE OF OLEFINS AND PROTON DONORS. SYNTHESIS OF 5-ALKYL-2(5<i>H</i>)-FURANONES
  作者：Pangbu Hong、Takaya Mise、Hiroshi Yamazaki

  DOI：10.1246/cl.1981.989

  日期：1981.7.5

  reactions of internal acetylenes with ethylene and CO in protic solvents, e.g., ethanol, gave 3,4-disubstituted-5-ethyl-2(5H)-furanones in good yields. By using propylene or methyl acrylate instead of ethylene, small amounts of 5-n-/iso-propyl-2(5H)-furanones or 5-[2-(methoxycarbonyl)ethyl]-2(5H)-furanone were obtained.

  铑羰基催化的内乙炔与乙烯和 CO 在质子溶剂（例如乙醇）中的反应以良好的收率得到 3,4-二取代-5-乙基-2(5H)-呋喃酮。通过使用丙烯或丙烯酸甲酯代替乙烯，得到少量的 5-n-/异丙基-2(5H)-呋喃酮或 5-[2-(甲氧基羰基)乙基]-2(5H)-呋喃酮。
• Regioselective 1,6-conjugate addition of organocuprate reagents to γ-alkylidenebutenolides
  作者：Anthony Vivien、Alexandra Bartoli、Jean-Luc Parrain、Laurent Commeiras

  DOI：10.1016/j.tetlet.2019.151472

  日期：2020.2

  This work describes the study of behavior of the δ-substituted and δ-non-substituted exo-cyclic double bond of γ-alkylidenebutenolides with dialkylcuprates. The addition reaction was found to be regioselective to afford the 1,6-conjugate adduct up to 87% yield.

  这项工作描述δ取代和δ-非取代的行为的研究外γ-alkylidenebutenolides与dialkylcuprates的-环双键。发现加成反应是区域选择性的，以提供高达87％收率的1，6-缀合物加合物。
• Efficient one-step synthesis of trialkylsubstituted 2(5H)-furanones utilizing direct Ti-crossed aldol condensation and its application to the straightforward synthesis of (R)-mintlactone and (R)-menthofuranElectronic supplementary information (ESI) available: calculated structures of 7 and 8. See http://www.rsc.org/suppdata/cc/b2/b208077j/
  作者：Yoo Tanabe、Kumi Mitarai、Takahiro Higashi、Tomonori Misaki、Yoshinori Nishii

  DOI：10.1039/b208077j

  日期：2002.10.18

  TiCl4–Bu3N-mediated condensation of ketones with α,α-dimethoxyketones afforded trialkylsubstituted 2(5H)-furanones in a one-pot manner, wherein aldol addition and furanone formation occurred sequentially; its application to straightforward synthesis of (R)-mintlactone and (R)-menthofuran, two representative natural mint perfumes, is demonstrated.

  TiCl4-Bu3N 介导的酮与α,α-二甲氧基酮的缩合以一锅方式得到了三烷基取代的 2(5H)-呋喃酮，其中醛醇加成和呋喃酮的形成依次发生；展示了其在直接合成(R)-薄荷内酯和(R)-薄荷呋喃（两种具有代表性的天然薄荷香水）中的应用。
• Ruthenium Carbene Complexes with <i>N</i>,<i>N</i>‘-Bis(mesityl)imidazol-2-ylidene Ligands:  RCM Catalysts of Extended Scope
  作者：Alois Fürstner、Oliver R. Thiel、Lutz Ackermann、Hans-Jörg Schanz、Steven P. Nolan

  DOI：10.1021/jo9918504

  日期：2000.4.1

  The ruthenium carbene complexes 3a,b bearing imidazol-2-ylidene ligands constitute excellent precatalysts for ring-closing metathesis (RCM) reactions allowing the formation of tri- and tetrasubstituted cycloalkenes. They also apply to annulations that are beyond the scope of the standard Grubbs carbene 1 as well as to ring-closing reactions of acrylic acid derivatives even if the resulting alpha,beta-unsaturated lactones (or lactams) are tri- or tetrasubstituted. The reactivity of 3a was found to be highly dependent on the reaction medium: particularly high reaction rates are observed in toluene, although this solvent also leads to an increased tendency of the catalyst to isomerize the double bonds of the substrates.
• XON PAMBU; MISEH TAKAYA; YAMADZAKI XIROSI; HON PAMBU; MISE TAKAUA; YAMAZA+, SEKUBAJ. SNOKUVAI, CATALYST, 1981, 23, NO 1, 42-44
  作者：XON PAMBU、 MISEH TAKAYA、 YAMADZAKI XIROSI、 HON PAMBU、 MISE TAKAUA、 YAMAZA+

  DOI：——

  日期：——