5-ethyl-5-phenylfuran-2(5H)-one | 143766-64-7

• 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-5-phenylfuran-2(5H)-one
• 英文别名: 5-Ethyl-5-phenylfuran-2-one
• CAS: 143766-64-7
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: LACPCHOYXSFUBZ-UHFFFAOYSA-N

物化性质

• 沸点：
  340.2±31.0 °C(Predicted)
• 密度：
  1.108±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：

  甲基碘化镁 、 5-ethyl-5-phenylfuran-2(5H)-one 以 乙醚 为溶剂， 生成 (Z)-2-Methyl-5-phenylhept-3-en-2,5-diol
  参考文献：
  名称：

  旋光性α，β-不饱和γ-内酯：烯丙基羧酸的立体定向转变

  摘要：

  描述了手性烯丙基羧酸及其酯转化为α，β-不饱和γ-内酯的条件。发现在3a和3b的情况下，内酯化反应是完全立体定向的。已经确定标题和相关化合物的构型和光学纯度。

  DOI：

  10.1016/0040-4020(78)80035-0
• 作为产物：
  描述：

  在 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.0h， 生成 5-ethyl-5-phenylfuran-2(5H)-one
  参考文献：
  名称：

  Lithium 3-Lithio-3-tosylalkanoates: .beta.-Acylvinyl Anion Equivalents of .beta.-Lithiated .alpha.,.beta.-Unsaturated Carboxylic Acids

  摘要：

  The dilithiation of beta-tosylated propanoic, 2-methylpropanoic, and butanoic acid 10 with n-butyllithium at -78 degrees C leads to the corresponding lithium 3-lithio-3-tosylalkanoates 11. They react with different electrophilic reagents (deuterium oxide, iodine, trimethylchlorosilane, alkyl halides, and acyl chlorides) to give the corresponding 3-substituted tosylated alkanoic acids 12. When carbonyl compounds are allowed to react with intermediates 11 followed by in situ lactonization with trifluoracetic anhydride and base-promoted elimination alpha,beta-butenolides are obtained. This methodology is applied to the direct synthesis of the rosefuran lactone precursor 14cg, the O-benzyl derivative of (+/-)-umbelactone (14ch), and (+/-)-andirolactone (14ci). The alkylation and acylation reactions of organolithium compounds 11 followed by esterification with hydrogen chloride in methanol and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afford alpha,beta- and/or beta,gamma-unsaturated esters 17 and/or 18 and unsaturated 4-keto esters 19, respectively. The last methodology has been applied to the synthesis of the unsaturated 4-keto ester 19ae precursor of the seco acid of (+/-)-pyrenophorin (22).

  DOI：

  10.1021/jo00090a043

文献信息

• Lithium 3-lithio-3-tosylpropanoate: A useful α-tosylated homoenolate anion
  作者：Pedro Bonete、Carmen Nájera

  DOI：10.1016/0040-4039(92)88101-a

  日期：1992.7

  Lithium 3-lithio-3-tosylpropanoate (7), prepared by dilithiation of 3-tosylpropanoic acid (6) with n-butyllithium at −78°C, reacts with different elctrophiles yielding the expected 3-functionalized tosylated propanoic acids 8. When carbonyl compounds are used as electrophiles the corresponding α,β-butenolides are prepared directly.

  通过在-78°C下将3-甲苯基丙酸（6）与正丁基锂二锂化制备的3-lithio-3-甲苯基丙酸锂（7）与不同的亲电子试剂反应生成预期的3-官能化甲苯磺酸丙酸8。当羰基化合物用作亲电试剂时，可以直接制备相应的α，β-丁烯内酯。
• Convenient synthesis of α,β-unsaturated γ-butyrolactones and γ-butyrolactams via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams using 1,3-diiodo-5,5-dimethylhydantoin
  作者：Supasorn Phae-nok、Chutima Kuhakarn、Manat Pohmakotr、Vichai Reutrakul、Darunee Soorukram

  DOI：10.1039/c5ob01574j

  日期：——

  A convenient synthetic approach to α,β-unsaturated γ-butyrolactones and α,β-unsaturated γ-butyrolactams is developed. The reaction proceeds via decarboxylative iodination of paraconic acids and β-carboxyl-γ-butyrolactams, employing 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation, followed by dehydroiodination of β-iodo-γ-butyrolactones and γ-butyrolactams providing good yields of α,β-unsaturated

  开发了一种简便的合成方法，合成α，β-不饱和γ-丁内酯和α，β-不饱和γ-丁内酰胺。该反应通过在辐射下使用1,3-二碘-5,5-二甲基乙内酰脲（DIH）对对苯二甲酸和β-羧基-γ-丁内酰胺进行脱羧碘化，然后对β-碘-γ-丁内酯和γ-进行加氢碘化来进行。丁内酰胺可提供高产率的α，β-不饱和γ-丁内酯和γ-丁内酰胺，它们是有机合成中合成有用的组成部分。
• Synthesis of 2-(5H)-furanones by cyclization of alkyl allene carboxylates in triflic acid
  作者：Oussama Abdelhamid Mammeri、Ilia M. Baranov、Alexandr Yu Ivanov、Irina A. Boyarskaya、Aleksander V. Vasilyev

  DOI：10.1016/j.tet.2023.133649

  日期：2023.10

  (triflic acid, TfOH) at room temperature or 70 °C for 30 min are cyclized to form 2-(5H)-furanones in yields up to 83%. The reaction cationic intermediates, O-monoprotonated [R2(R3)C=C=C(R1)–C(=O+H)OAlk] and O,C-diprotonated [R2(R3)C+–CH=C(R1)–C(=O+H)OAlk] forms of starting allenes, have been studied experimentally by NMR and theoretically by DFT calculations. It has been found that the cyclization proceeds

  烷基丙二烯羧酸盐 [R 2 (R 3 )C=C=C(R 1 )–C(=O)OAlk] 在 Brønsted 超强酸 CF 3 SO 3 H（三氟甲磺酸，TfOH）中，室温或 70 °C 30 min 环化形成 2-(5 H )-呋喃酮，产率高达 83%。反应阳离子中间体，O-单质子化 [R 2 (R 3 )C=C=C(R 1 )–C(=O + H)OAlk] 和 O,C-二质子化 [R 2 (R 3 )C + – CH=C(R 1 )–C(=O + H)Olk] 形式的起始丙二烯，已通过 NMR 进行了实验研究并在理论上通过 DFT 计算。已发现环化通过起始丙二烯的O,C-二质子化形式进行。