3-acetyl-4-(N,N-dibenzylamino)-3-cyclobutene-1,2-dione | 172979-18-9

• 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-acetyl-4-(N,N-dibenzylamino)-3-cyclobutene-1,2-dione
• 英文别名: 3-Acetyl-4-(dibenzylamino)cyclobut-3-ene-1,2-dione
• CAS: 172979-18-9
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: FULWINPUQABEFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 三丁基(4,5-二氢呋喃-2-基)锡烷 、 3-acetyl-4-(N,N-dibenzylamino)-3-cyclobutene-1,2-dione 在 正丁基锂 作用下， 生成 4-acetoxy-2-acetyl-3-(N,N-dibenzylamino)-4-(2,3-dihydrofuran-5-yl)-2-cyclobuten-1-one
  参考文献：
  名称：

  Construction of Highly-Substituted Aromatics Bearing Acyl Substituents Using Cyclobutenedione Technology: Vinylketene-Based Benzannulations Using 3-Acyl-4-(substituted amino)cyclobutenediones

  摘要：

  Highly-substituted acylated aromatics were efficiently synthesized from 3-acylcyclobutenediones via vinylketene-based benzannulations. Aryl and alkenyl lithiates added regioselectively to 3-acyl-4-(substituted amino)-3-cyclobutene-1,2-diones at -78 degrees C to produce the corresponding 4-aryl- and 4-alkenyl-3-(substituted amino)-2-acylcyclobutenones in good yields. Substrates lacking the vinylogous amide functionality were not preparable by this route, because the acylcyclobutenedione starting materials are not sufficiently stable to manipulate. Benzannulations of 4-(3-furyl)-, 4-(2-thienyl)-, 4-(2-dihydropyranyl)-, 4-(2-dihydrofuranyl)-, 4-(1-naphthyl)-, and 4-(2-naphthyl)substituted cyclobutenones proceeded in refluxing mesitylene to give the corresponding acyl aromatics in 80-90% yield. Of all the 4-arylcyclobutenones synthesized (aryl = phenyl and substituted phenyl), only those with an electron-donating substituent (OMe, NMe(2)) at the meta position of phenyl group underwent benzannulation in refluxing mesitylene to afford acyl aromatics in moderate yields.

  DOI：

  10.1021/jo00130a018
• 作为产物：
  描述：

  3-(1-甲基乙氧基)-4-(三丁基锡烷基)-3-环丁烯-1,2-二酮 、 乙酰氯 、 二苄胺 在 copper(l) iodide 、 benzoylchlorobis(triphenylphosphine)palladium(II) 作用下， 以89%的产率得到3-acetyl-4-(N,N-dibenzylamino)-3-cyclobutene-1,2-dione
  参考文献：
  名称：

  Construction of Highly-Substituted Aromatics Bearing Acyl Substituents Using Cyclobutenedione Technology: Vinylketene-Based Benzannulations Using 3-Acyl-4-(substituted amino)cyclobutenediones

  摘要：

  Highly-substituted acylated aromatics were efficiently synthesized from 3-acylcyclobutenediones via vinylketene-based benzannulations. Aryl and alkenyl lithiates added regioselectively to 3-acyl-4-(substituted amino)-3-cyclobutene-1,2-diones at -78 degrees C to produce the corresponding 4-aryl- and 4-alkenyl-3-(substituted amino)-2-acylcyclobutenones in good yields. Substrates lacking the vinylogous amide functionality were not preparable by this route, because the acylcyclobutenedione starting materials are not sufficiently stable to manipulate. Benzannulations of 4-(3-furyl)-, 4-(2-thienyl)-, 4-(2-dihydropyranyl)-, 4-(2-dihydrofuranyl)-, 4-(1-naphthyl)-, and 4-(2-naphthyl)substituted cyclobutenones proceeded in refluxing mesitylene to give the corresponding acyl aromatics in 80-90% yield. Of all the 4-arylcyclobutenones synthesized (aryl = phenyl and substituted phenyl), only those with an electron-donating substituent (OMe, NMe(2)) at the meta position of phenyl group underwent benzannulation in refluxing mesitylene to afford acyl aromatics in moderate yields.

  DOI：

  10.1021/jo00130a018

文献信息

• Construction of Highly-Substituted Aromatics Bearing Acyl Substituents Using Cyclobutenedione Technology: Vinylketene-Based Benzannulations Using 3-Acyl-4-(substituted amino)cyclobutenediones
  作者：Lijun Sun、Lanny S. Liebeskind

  DOI：10.1021/jo00130a018

  日期：1995.12

  Highly-substituted acylated aromatics were efficiently synthesized from 3-acylcyclobutenediones via vinylketene-based benzannulations. Aryl and alkenyl lithiates added regioselectively to 3-acyl-4-(substituted amino)-3-cyclobutene-1,2-diones at -78 degrees C to produce the corresponding 4-aryl- and 4-alkenyl-3-(substituted amino)-2-acylcyclobutenones in good yields. Substrates lacking the vinylogous amide functionality were not preparable by this route, because the acylcyclobutenedione starting materials are not sufficiently stable to manipulate. Benzannulations of 4-(3-furyl)-, 4-(2-thienyl)-, 4-(2-dihydropyranyl)-, 4-(2-dihydrofuranyl)-, 4-(1-naphthyl)-, and 4-(2-naphthyl)substituted cyclobutenones proceeded in refluxing mesitylene to give the corresponding acyl aromatics in 80-90% yield. Of all the 4-arylcyclobutenones synthesized (aryl = phenyl and substituted phenyl), only those with an electron-donating substituent (OMe, NMe(2)) at the meta position of phenyl group underwent benzannulation in refluxing mesitylene to afford acyl aromatics in moderate yields.