5-ethyl-2-methyl-3(2H)-furanone | 82782-13-6

• 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-2-methyl-3(2H)-furanone
• 英文别名: 2-Methyl-5-ethyl-3(2H)-furanone；5-ethyl-2-methylfuran-3-one
• CAS: 82782-13-6
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: SKJNEYSTLJSDDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  trifluoro-methanesulfonic acid 3-isopropyl-3-methoxy-3a-methyl-4-oxo-6-vinyl-tetrahydro-furo[3,4-c]furan-1-ylmethyl ester 、 5-ethyl-2-methyl-3(2H)-furanone 在 双(三甲基硅烷基)氨基钾 作用下， 以 甲苯 为溶剂， 反应 2.83h， 以38%的产率得到4-(5-ethyl-2-methyl-3-oxo-2,3-dihydro-furan-2-ylmethyl)-6-isopropyl-6-methoxy-6a-methyl-3-vinyl-tetrahydro-furo[3,4-c]furan-1-one
  参考文献：
  名称：

  抗肿瘤倍半萜类（+）-香叶内酯A的不对称全合成和形式全合成。

  摘要：

  [结构：见文字]。报道了一种新的不对称全合成（+）-香叶内酯A，其中使用了Hoveyda-Grubbs闭环复分解（RCM）反应组装了九元氧代宁环，并使3（2H）-之间的烯醇化烷基化。呋喃酮2和O-三氟甲磺酸3用于C（9）-C（10）键结构。埃文斯（Evans）不对称羟醛反应和Sharpless不对称环氧化用于立体选择性地安装目标结构的C（6），C（7）和C（8）立体中心。

  DOI：

  10.1021/ol0700862
• 作为产物：
  描述：

  1-(3-乙基-1,2-恶唑-5-基)乙酮 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 13.0h， 生成 5-ethyl-2-methyl-3(2H)-furanone
  参考文献：
  名称：

  New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity

  摘要：

  A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00776-2

文献信息

• Process for the preparation of naphthalen-2-yl-pyrazol-3-one intermediates useful in the synthesis of sigma receptor inhibitors
  申请人：Laboratorios Del. Dr. Esteve, S.A.

  公开号：EP2112139A1

  公开（公告）日：2009-10-28

  The invention relates to a process for preparing naphthalen-2-yl-pyrazol-3-one intermediates, tautomers, and salts thereof, to novel intermediates, and to the use of the intermediates in the preparation of sigma receptor inhibitors.

  这项发明涉及一种制备萘-2-基吡唑-3-酮中间体、互变异构体及其盐的过程，涉及新型中间体，并涉及将这些中间体用于制备σ受体抑制剂。
• Andersen, Soeren H.; Das, Nalin B.; Joergensen, Ruth D., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1982, vol. 36, # 1, p. 1 - 14
  作者：Andersen, Soeren H.、Das, Nalin B.、Joergensen, Ruth D.、Kjeldsen, Gunhild、Knudsen, Jes S.、et al.

  DOI：——

  日期：——
• A total synthesis of (+)-eremantholide A
  作者：Ken-ichi Takao、Hiroshi Ochiai、Takahiko Hashizuka、Hirokazu Koshimura、Kin-ichi Tadano、Seiichiro Ogawa

  DOI：10.1016/0040-4039(95)00066-l

  日期：1995.2

  Stereoselective and enantiospecific total synthesis of (+)-eremantholide A (1) is described. The present total synthesis features 1) regio- and stereoselective radical carbocyclization of D-glurose-derived gamma-lactone 7, and 2) a nine-membered ring formation by the coupling reaction of bicyclic triflate 18 and known furanone 19 followed by a vinylogous aldol reaction.
• Novel Total Synthesis of (+)-Eremantholide A
  作者：Ken-ichi Takao、Hiroshi Ochiai、Ken-ichi Yoshida、Takahiko Hashizuka、Hirokazu Koshimura、Kin-ichi Tadano、Seiichiro Ogawa

  DOI：10.1021/jo00130a017

  日期：1995.12

  Stereoselective total synthesis of (+)-eremantholide A (1), a cytotoxic furanoheliangolide sesquiterpene, was accomplished in an enantiospecific fashion. The total synthesis featured the following three key synthetic strategies. (1) Intramolecular cyclization of carbon-radicals derived from xanthates 19a or 19b proceeded regio- and stereoselectively in an exclusive 5-exo-dig mode to provide bicyclic lactones 20a or 20b. Further functional group manipulations of 20a and 20b efficiently afforded a highly substituted 3,7-dioxabicyclo[3.3.0]octan-2-one derivative 34, which served as a synthetic equivalent to the A/B ring system in 1. (2) Alkylation of the enolate of 3(2H)-furanone 36 with triflate 35 was thoroughly investigated to maximize formation of the C-alkylated diastereomers, either 10R-isomer 37 or 10S-isomer 38. It was found that choice of the base, solvent, and/or additive was critical to the diastereoselectivity. Furthermore, the 10R-isomer 50 was also prepared in increased yield and improved diastereoselectivity by coupling 36 with A/B ring equivalent 49. (3) In a later stage of the total synthesis, construction of the strained 11-oxabicyclo-[6.2.1]undeca-2,10-dien-9-one system (the C/D ring) was accomplished by means of an intramolecular vinylogous aldol reaction of aldehyde 52, prepared from 10R-isomer 40, followed by base-catalyzed beta-elimination of the corresponding mesylates 54. On the other hand, by employing analogous reaction conditions, the 10S-isomer 56 was transformed into unnatural (-)-10-epi-eremantholide A (61).
• DIARYL[A, G]QUINOLIZIDINE COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION, AND USES THEREOF
  申请人：Shanghai Institute of Materia Medica, Chinese Academy of Sciences

  公开号：EP2848617B1

  公开（公告）日：2022-01-12