1-(2-(氯甲基)-5-苯基呋喃-3-基)乙酮 | 281198-93-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-(氯甲基)-5-苯基呋喃-3-基)乙酮
• 英文名称: 3-acetyl-2-chloromethyl-5-phenylfuran
• 英文别名: 1-(2-(Chloromethyl)-5-phenylfuran-3-YL)ethanone；1-[2-(chloromethyl)-5-phenylfuran-3-yl]ethanone
• CAS: 281198-93-4
• 化学式: C₁₃H₁₁ClO₂
• 分子量: 234.682
• InChiKey: VNKATXNPMLRQQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  378.0±42.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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-(氯甲基)-5-苯基呋喃-3-基)乙酮 在 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以82%的产率得到3-acetyl-2-hydroxymethyl-5-phenylfuran
  参考文献：
  名称：

  Synthesis of polyfunctionalized furans from 3-acetyl-1-aryl-2-pentene-1,4-diones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(02)01597-1
• 作为产物：
  描述：

  3-乙酰基-1-苯基戊-2-烯-1,4-二酮 在 盐酸 作用下， 以87%的产率得到1-(2-(氯甲基)-5-苯基呋喃-3-基)乙酮
  参考文献：
  名称：

  酸催化将1-芳基-2-戊烯-1,4-二酮方便地转化为多官能呋喃

  摘要：

  苯乙二醛与2,4-戊二酮在三氟化硼的存在下反应，生成了不稳定的3-乙酰基-1-苯基-2-戊烯-1,4-二酮中间体，该中间体通过反应与过量的三氟甲磺酸原位转化。 2,4-戊二酮变成新的结晶的三取代和四取代的呋喃。通过3-乙酰基-5-芳基-2-甲基呋喃的光氧化作用获得的其他不稳定的1-芳基-2-戊烯-1,4-二酮不稳定，通过酸催化反应被捕获，从而以高收率得到多官能化的呋喃。用浓盐酸处理1-苯基-2-戊烯-1，4-二酮中间体，然后将乙醇煮沸，通过不稳定的2-氯甲基呋喃定量产生稳定的2-乙氧基甲基呋喃。

  DOI：

  10.1016/s0040-4039(00)00373-7

文献信息

• Acid-catalyzed convenient transformation of 1-aryl-2-pentene-1,4-diones into polyfunctionalized furans
  作者：Satoaki Onitsuka、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1016/s0040-4039(00)00373-7

  日期：2000.4

  of boron trifluoride gave the unstable 3-acetyl-1-phenyl-2-pentene-1,4-dione intermediate which was converted in situ by the reaction with an excess amount of 2,4-pentanedione into new crystalline tri- and tetra-substituted furans. Other unstable 1-aryl-2-pentene-1,4-diones, which were obtained by the photooxygenation of 3-acetyl-5-aryl-2-methylfurans, were trapped by the acid-catalyzed reaction, giving

  苯乙二醛与2,4-戊二酮在三氟化硼的存在下反应，生成了不稳定的3-乙酰基-1-苯基-2-戊烯-1,4-二酮中间体，该中间体通过反应与过量的三氟甲磺酸原位转化。 2,4-戊二酮变成新的结晶的三取代和四取代的呋喃。通过3-乙酰基-5-芳基-2-甲基呋喃的光氧化作用获得的其他不稳定的1-芳基-2-戊烯-1,4-二酮不稳定，通过酸催化反应被捕获，从而以高收率得到多官能化的呋喃。用浓盐酸处理1-苯基-2-戊烯-1，4-二酮中间体，然后将乙醇煮沸，通过不稳定的2-氯甲基呋喃定量产生稳定的2-乙氧基甲基呋喃。
• 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.