1,4-diphenyl-1,4-dihydro-[1,2,4,5]tetrazine-3,6-dicarboxylic acid diethyl ester | 4397-78-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,4-diphenyl-1,4-dihydro-[1,2,4,5]tetrazine-3,6-dicarboxylic acid diethyl ester
• 英文别名: 1,4-Diphenyl-1,4-dihydro-[1,2,4,5]tetrazin-3,6-dicarbonsaeure-diaethylester；[1,2,4,5]Tetrazine-3,6-dicarboxylic acid, 1,4-diphenyl-1,4-dihydro-, diethyl ester；diethyl 1,4-diphenyl-1,2,4,5-tetrazine-3,6-dicarboxylate
• CAS: 4397-78-8
• 化学式: C₂₀H₂₀N₄O₄
• 分子量: 380.403
• InChiKey: LIDMQSXCEOQXND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (phenylhydrazono)chloroacetate 在 (2-氧代-2-苯乙基)膦酸二乙酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 1,4-diphenyl-1,4-dihydro-[1,2,4,5]tetrazine-3,6-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates

  摘要：

  A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with beta-oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition-elimination sequence. Wide scope, functional group compatibility has been established. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.045

文献信息

• Rate enhancement of 1,3-dipolar cycloaddition ofN-methylindole: the singular role of Grignard reagents
  作者：Tiziana Benincori、Franco Sannicol�、Licia Trimarco、Laura Bonati、Stefania Grandi、Demetrio Pitea、Carlo Gatti

  DOI：10.1002/(sici)1099-1395(199807)11:7<455::aid-poc998>3.0.co;2-5

  日期：1998.7

  The reactions of 2-N-methylindolyl and 2- and 3-benzo[b]thiophenyl anions with nitrile oxides and nitrilimines were performed in order to investigate whether the use of anionic dipolarophiles modifies a classical 1,3-dipolar cycloaddition. When lithium compounds were used as bases, the heterocyclic anions invariably acted as nucleophilic species; in contrast, when a Grignard reagent was employed, the N-methylindole gave cycloaddition products with an extraordinary rate enhancement. The hypothesis that N-methylindole and ethylmagnesium bromide give an adduct much more reactive than N-methylindole itself was supported by the results of a theoretical investigation. The structure and electron distribution of the adduct were determined by ab initio calculations and compared with those of known Grignard complexes with nitrogen ligands. The performance of different basis sets was tested. The quantum theory of atoms in molecules was used to determine atomic charges and to describe the nature of bonds in terms of the properties of the electron density at the bond critical points. (C) 1998 John Wiley & Sons, Ltd.
• Petrov, M. L.; Terent'eva, N. A.; Potekhin, K. A., Russian Journal of Organic Chemistry, 1993, vol. 29, # 7.1, p. 1137 - 1142
  作者：Petrov, M. L.、Terent'eva, N. A.、Potekhin, K. A.、Struchkov, Yu. T.

  DOI：——

  日期：——
• XERUZE YU. I.; CHISTOKLETOV V. N.; PETROV A. A., ZH. ORGAN. XIMII, 1978, 14, HO 7, 1396-1401
  作者：XERUZE YU. I.、 CHISTOKLETOV V. N.、 PETROV A. A.

  DOI：——

  日期：——
• US7329651B2
  申请人：——

  公开号：US7329651B2

  公开（公告）日：2008-02-12
• A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates
  作者：Aixue Sun、Jia-Hai Ye、Haitao Yu、Wenchao Zhang、Xiaolong Wang

  DOI：10.1016/j.tetlet.2013.12.045

  日期：2014.1

  A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with beta-oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition-elimination sequence. Wide scope, functional group compatibility has been established. (C) 2013 Elsevier Ltd. All rights reserved.