2-Diazo-3,5-dioxo-5-p-tolyl-pentanoic acid ethyl ester | 78344-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Diazo-3,5-dioxo-5-p-tolyl-pentanoic acid ethyl ester
• CAS: 78344-66-8
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: MUUBYHWTPDJMAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-Diazo-3,5-dioxo-5-p-tolyl-pentanoic acid ethyl ester 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以80%的产率得到ethyl 5-(4-methylbenzoyl)-4-oxo-1,5-dihydropyrazole-3-carboxylate
  参考文献：
  名称：

  Andreichikov, Yu.S.; Gein, L.F.; Gein, V.L., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 545 - 550

  摘要：

  DOI：
• 作为产物：
  描述：

  5-(4-甲基苯基)呋喃-2,3-二酮 生成 2-Diazo-3,5-dioxo-5-p-tolyl-pentanoic acid ethyl ester
  参考文献：
  名称：

  Zalesov; Posyagin; Vyaznikova, Russian Journal of General Chemistry, 2000, vol. 70, # 1, p. 81 - 87

  摘要：

  DOI：

文献信息

• Synthesis of Trifunctionalized Naphtho[1,2-<i>b</i>]furans Based on the Strategy for the Construction of Both Furan and Naphthalene Cycle
  作者：Shanjian Mao、Yinbo Wan、Haiyun Peng、Li Luo、Guisheng Deng

  DOI：10.1021/acs.joc.9b00058

  日期：2019.5.3

  available conjugated diazo ene-yne-ketones under O2 atmosphere led to the formation of diazo trisubstituted furans. The Rh2(OAc)4-mediated selective C(sp2)–H insertion at the ortho-position of 2-aryl group (R1) of the furan moiety under N2 atmosphere occurred to construct naphthalene cycle, affording trifunctionalized naphtho[1,2-b]furans. C(sp2)–H insertion at the 4-position of the furan ring, and Wolf rearrangement

  在O 2气氛下，Pd（PPh 3）2 Cl 2催化可利用的共轭重氮烯-炔酮选择性串联环化/氧化导致重氮三取代呋喃的形成。在N 2气氛下，Rh 2（OAc）4介导的选择性C（sp 2）–H插入呋喃部分的2-芳基（R 1）的邻位构成了萘循环，从而提供了三官能化萘[ 1,2- b ]呋喃。尚未观察到呋喃环4位上的C（sp 2）–H插入和重氮部分的Wolf重排。
• Chemistry of Diazopolycarbonyl Compounds: VIII. Synthesis of Nitrogen-containing Heterocycles via Transformations of Substituted 2-diazopentane-1,3,5-triones
  作者：N. V. Kutkovaya、N. G. Vyaznikova、V. V. Zalesov

  DOI：10.1023/b:rujo.0000013140.10977.7f

  日期：2003.11

  Ethyl 5-aryl-2-diazo-3,5-dioxopentanoates and 1,5-diaryl-2-diazopentane-1,3,5-triones are partially enolized in solutions. By O-methylation of enol forms of diazo esters with diazomethane ethyl 5-aryl-2-diazo-5-methoxy-3-oxopent-4-enoates were prepared. Concurrently with the O-methylation the diazo esters undergo heterocyclization into 3,5-disubstituted 4-hydroxypyrazoles which under the reaction condition suffer O- and N-methylation by excess diazomethane. 3,5-Diaroyl-4-hydroxypyrazoles were also obtained from diazopentanetriones but here triethylamine served as the cyclization reagent.