1-(2-甲基-5-(对甲苯基)呋喃-3-基)乙酮 | 43020-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-甲基-5-(对甲苯基)呋喃-3-基)乙酮
• 英文名称: 1-(2-methyl-5-(p-tolyl)furan-3-yl)ethanone
• 英文别名: 3-acetyl-5-(4-methylphenyl)-2-methylfuran；1-(2-methyl-5-p-tolyl-furan-3-yl)-ethanone；4-Acetyl-2-p-tolyl-5-methyl-furan；2-Methyl-3-acetyl-5-(4-methylphenyl)furan；1-[2-methyl-5-(4-methylphenyl)furan-3-yl]ethanone
• CAS: 43020-14-0
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: GCNRBAIODYJQQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-甲基-5-(对甲苯基)呋喃-3-基)乙酮 在 氧气 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以30%的产率得到3-acetyl-2-hydroxy-1-(4-methylphenyl)-2-pentene-1,4-dione
  参考文献：
  名称：

  Photooxygenation of 3-acetyl-5-aryl-2-methylfurans via endoperoxide intermediate and the following reactions

  摘要：

  The photooxygenation of 3-acetyl-5-aryl-2-methylfurans la-e selectively produced 2,2-diacetyl-3-aroyloxiranes 2a-e, 3-acetyl-1-aryl-2-pentene-1,4-diones 3a-e, and 3-acetyl-1-aryl-2-hydroxy-2-pentene-1,4-diones 4a-d via the endoperoxide intermediate A depending on the reaction conditions and the work-up procedure. The oxiranes 2a-e were mainly obtained in 56-77% yields by allowing the reaction mixture to stand at ambient temperature after the irradiation, while the treatment of the reaction mixture with water mainly gave the 1,4-diones 3a-e (62-69%). Heating the reaction mixture at 80 degreesC after the irradiation decreased the total yield of the products, however, the enols 4a-d were newly formed in 8-12% yields. Direct UV irradiation of the endoperoxide intermediate A led to the homolytic fission of the peroxide linkage to produce the same enols 4a-e (16-39%). The self-sensitized photooxygenation of 1a-d using a UV light also gave 4a-d in a similar yield. The reaction pathway is discussed based on these results. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00559-2
• 作为产物：
  描述：

  4-acetyl-3-methyl-6,6-bis(4-methylphenyl)-1,2-dioxan-3-ol 在 高氯酸 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以92%的产率得到1-(2-甲基-5-(对甲苯基)呋喃-3-基)乙酮
  参考文献：
  名称：

  Qian, Chang-Yi; Hirose, Jun-ichi; Nishino, Hiroshi, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 5, p. 1219 - 1228

  摘要：

  DOI：

文献信息

• Manganese(II and III)-Mediated Synthesis of Cyclic Peroxides from Alkenes, Active Methylene Compounds, and Molecular Oxygen
  作者：Chang-Yi Qian、Takashi Yamada、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1246/bcsj.65.1371

  日期：1992.5

  2-acetylcyclohexanone, ethyl 2-acetyl-3-oxobutanoate, 3-methyl-2,4-pentanedione, 1,3-cyclohexanedione, and 2,4-pentanedione in the presence of Mn(OAc)2 and molecular oxygen yielded the corresponding cyclic peroxides in moderate-to-good yields. Similar reaction of 1,1-disubstituted alkenes with 1,3-cyclopentanedione in the presence of Mn(OAc)3 and molecular oxygen gave 2,2,9,9-tetraphenyloctahydro-3,4

  1,1-二苯基乙烯、1,1-双(4-氯苯基)乙烯、1,1-双(4-甲基苯基)乙烯、1,1-双(4-甲氧基苯基)乙烯和1,1-的反应双（4-氟苯基）乙烯与 2-甲基-1,3-环己二酮、2-甲基-1,3-环戊二酮、2-乙酰环己酮、2-乙酰-3-氧代丁酸乙酯、3-甲基-2,4-戊二酮在Mn(OAc)2 和分子氧的存在下，1,3-环己二酮和2,4-戊二酮以中等至良好的产率产生相应的环状过氧化物。在Mn(OAc)3 和分子氧存在下，1,1-二取代烯烃与1,3-环戊二酮的类似反应得到2,2,9,9-四苯基八氢-3,4,7,8-四氧苯并[c]茚-4a,6a-二醇。4-乙酰基-6,6-二芳基-3-甲基-1,2-二恶烷-3-醇的酸催化分解以中等产率得到3-乙酰基-5-芳基-2-甲基呋喃。4-乙酰基-6,6-二芳基-3-甲基-1的处理，2-二恶烷-3-醇与碱一起得到6,6-二芳基-3-甲基-1,2-二恶烷-3
• Selective Formation of 2,3,5‐Trisubstituted Furans from 1,3‐Dicarbonyls and Hydroxyketones
  作者：Wanying Yan、Jiaru Shou、Wenyi Qin、Jiayu Mo、Huawen Huang

  DOI：10.1002/adsc.202300860

  日期：2023.11.21

  Chemoselective cyclizations of 1,3-dicarbonyl compounds with hydroxyketones for the selective formation of two 2,3,5-trisubstituted furans have been reported. While TsOH-mediated cyclization in DCM afforded 2-acylfurans, the additional copper catalyst in acetone turned over the selectivity for the generation of 3-acylfurans. The featured advantages of both reactions include simple conditions, high

  已经报道了 1,3-二羰基化合物与羟基酮的化学选择性环化，以选择性形成两个 2,3,5-三取代呋喃。虽然 DCM 中 TsOH 介导的环化反应生成 2-酰基呋喃，但丙酮中额外的铜催化剂却改变了 3-酰基呋喃生成的选择性。两种反应均具有条件简单、收率高、底物范围广、克数可扩展、副产物为H 2 O等特点。
• Pd(II)-Catalyzed Sequential C–C/C–O Bond Formations: A New Strategy to Construct Trisubstituted Furans
  作者：Meifang Zheng、Liangbin Huang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/ol400451t

  日期：2013.4.19

  Palladium-catalyzed oxidative difunctionalization of enol ethers with 1,3-dicarbonyl compounds to construct trisubstituted furans in one step under mild conditions is described. The reaction is thought to proceed through a C-C bond formation along with a C-O bond closing the ring structure. Oxygen is the sole oxidant regenerating the Pd(II) catalyst.
• Synthesis of polyfunctionalized furans from 3-acetyl-1-aryl-2-pentene-1,4-diones
  作者：Satoaki Onitsuka、Hiroshi Nishino

  DOI：10.1016/s0040-4020(02)01597-1

  日期：2003.2

  The BF3-catalyzed cyclization of 3-acetyl-1-aryl-2-pentene-1,4-diones 1a-e in the presence of water in boiling tetrahydrofuran gave bis(3-acetyl-5-aryl-2-furyl)methanes 2a-e in 26-79% yields along with a small amount of 3-acetyl-5-aryl-2-methylfurans 3a-e. The exact structure of 2a was determined by X-ray crystallography. The use of a half volume of the solvent for the reaction of la resulted in the formation of 2,4-bis(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-phenylfuran (4) together with 2a and 3a. A similar reaction of la was carried out in the presence of 3-acetyl-5-(4-methylphenyl)-2-methylfuran (3d) to afford 4-(3-acetyl-5-phenyl-2-furfuryl)-3-acetyl-5-(4methylphenyl)-2-methylfuran (5) in 49% yield. The BF3-catalyzed reaction of la with 2,4-pentanedione in dry tetrahydrofuran at 23degreesC gave 3-(3-acetyl-5-phenyl-2-furfuryl)-4-hydroxy-3-penten-2-one (6a) and 3-(3-acetyl-2-methyl-4-phenyl-5-furyl)-4-hydroxy-3-penten-2one (7a) in 66 and 24% yields, respectively. The product distribution depended on the reaction temperature. A similar reaction of 1b-e also yielded the corresponding trisubstituted furans 6b-e and tetrasubstituted furans 7b-e in good yields. These results suggested the presence of the furfuryl carbocation intermediate A during the reaction. The one-pot synthesis of 6a and 7a was also achieved by a similar reaction using phenylglyoxal. The deoxygenation of la with triphenylphosphine gave 3a in 88% yield, while la was treated with concentrated hydrochloric acid to yield 3-acetyl-2-chloromethyl-5-phenylfuran (8) which was quantitatively transformed in ethanol into 3-acetyl-2-ethoxymethyl-5phenylfuran (9) and in water into 3-acetyl-5-phenylfurfuryl alcohol (10), respectively. In addition, the Diels-Alder reaction of cyclopantadiene with 1a gave the corresponding [4+2] cycloaddition products 11 and 12. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Qian, Chang-Yi; Hirose, Jun-ichi; Nishino, Hiroshi, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 5, p. 1219 - 1228
  作者：Qian, Chang-Yi、Hirose, Jun-ichi、Nishino, Hiroshi、Kurosawa, Kazu

  DOI：——

  日期：——