3-methyl-5-(4-chlorophenyl)-2(5H)-furanone | 85671-08-5

• 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: 3-methyl-5-(4-chlorophenyl)-2(5H)-furanone
• 英文别名: 5-(4-chlorophenyl)-3-methylfuran-2(5H)-one；5-(p-chlorophenyl)-3-methyl-2(5H)-furanone；2-(4-chlorophenyl)-4-methyl-2H-furan-5-one
• CAS: 85671-08-5
• 化学式: C₁₁H₉ClO₂
• 分子量: 208.644
• InChiKey: IUWUNONZJLBQOT-UHFFFAOYSA-N

物化性质

• 熔点：
  77-79 °C
• 沸点：
  370.0±42.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-(4-chlorophenyl)-4-(tetrahydropyran-2-yloxy)but-2-yn-1-ol 在 lithium aluminium tetrahydride 、 十二羰基三钌 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 100.0 ℃ 、1.01 MPa 条件下， 反应 11.0h， 生成 3-methyl-5-(4-chlorophenyl)-2(5H)-furanone
  参考文献：
  名称：

  Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines:  Selective Synthesis of Lactones and Lactams

  摘要：

  Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give gamma-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.

  DOI：

  10.1021/jo0350615

文献信息

• [4R]-3-(.omega.-Aroylpropionyl)-4-thiazolidinecarboxylic acids and esters
  申请人：American Cyanamid Company

  公开号：US04374249A1

  公开（公告）日：1983-02-15

  This disclosure describes novel [4R]-3-(.omega.-aroylpropionyl)-4-thiazolidinecarboxylic acids and esters and the cationic salts thereof which are useful as hypotensive agents in mammals.

  这份披露描述了新型的[4R]-3-(.omega.-芳酰基丙酰基)-4-噻唑烷甲酸及其酯以及相应的阳离子盐，它们在哺乳动物中作为降压剂是有用的。
• 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。
• Novel and efficient synthesis of 2(5H)-furanone derivatives
  作者：Yoo Tanabe、Nobuo Ohno

  DOI：10.1021/jo00242a043

  日期：1988.4
• TANABE, YOO;OHNO, NOBUO, J. ORG. CHEM., 53,(1988) N 7, 1560-1563
  作者：TANABE, YOO、OHNO, NOBUO

  DOI：——

  日期：——