乙基3-氨基-2-吲嗪羧酸酯 | 3351-78-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: 乙基3-氨基-2-吲嗪羧酸酯
• 英文名称: 3-Amino-2-indolizincarbonsaeure-ethylester
• 英文别名: ethyl 3-aminoindolisine-2-carboxylate；Ethyl-3-amino-indolizin-2-carboxylat；Ethyl 3-aminoindolizine-2-carboxylate
• CAS: 3351-78-8
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: HXPVTBZEUKQMKN-UHFFFAOYSA-N

物化性质

• 熔点：
  71-72 °C(Solv: ethanol (64-17-5))
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  56.73
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氰基-3-(吡啶-2-基)丙烯酸乙酯 在 二异丁基氢化铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.0h， 以45%的产率得到乙基3-氨基-2-吲嗪羧酸酯
  参考文献：
  名称：

  Flitsch, Wilhelm; Kahner-Groene, Sigrid, Chemische Berichte, 1982, vol. 115, # 3, p. 871 - 877

  摘要：

  DOI：

文献信息

• Reaction of 3-arylidenepropenoic acid derivatives with triethylamine and other amines; unexpected reductions and vinylogations
  作者：Attimogae Shivamurthy Harisha、Suresh Parameshwar Nayak、Kuppuswamy Nagarajan、Tayur Narasingarow Guru Row、Amar A. Hosamani

  DOI：10.1016/j.tet.2016.03.097

  日期：2016.6

  Exposure of ethyl 2-cyano-3-(2-methoxy-5-nitrophenyl)acrylate 1f to triethylamine in hot ethanol resulted in the formation of the dihydro derivative 2f and vinylogue 3f in high yields. Single crystal X-ray data are provided for 3f. Similar reactions were observed for various analogues. The reaction was studied changing aryl substituent, amines and solvents. Pyridyl, thienyl analogues were also examined

  在热乙醇中将2-氰基-3-（2-甲氧基-5-硝基苯基）丙烯酸乙酯1f暴露于三乙胺导致高产率地形成二氢衍生物2f和乙烯基化合物3f。提供了用于3f的单晶X射线数据。对于各种类似物观察到相似的反应。研究了改变芳基取代基，胺和溶剂的反应。还检查了吡啶基，噻吩基类似物。该研究扩展到包含这种系统，如噻唑烷二酮的环状分子8，3-氰基香豆素9和4-亚芳基-异喹啉-2,4-二酮11。最后一组给出了乙烯基化产物，4-肉桂基-异喹啉二酮和4-羟基化的物质。研究了来自丙二腈，乙酰乙酸乙酯，乙酰丙酮和甲基磺酰乙酸乙酯的亚芳基衍生物的一些实例。肉桂酸乙酯和β-硝基苯乙烯不受影响。由于添加自由基淬灭剂抑制了反应，因此认为该反应可能是自由基介导的。与热条件的影响相反，在254和365 nm的乙醇中1f的辐照产生复杂的混合物。在这项研究中还注意到了一些其他有趣的观察结果：1f与乙醛的乙烯基化反应生成3f；从1f形成3f用
• One-pot multistep synthesis of 3-aminoindolizine derivatives
  作者：Lianhai Li、Waepril Kimberly S. Chua

  DOI：10.1016/j.tetlet.2011.01.087

  日期：2011.3

  We have developed an efficient one-pot multistep sequence to the synthesis of 3-aminoindolizine derivatives by using Hantzsch ester (9) as a mild hydride transfer agent. The reaction scope was investigated and the effect of substrates on reaction outcomes was discussed. (C) 2011 Published by Elsevier Ltd.
• Applications of caged-designed proton sponges in base-catalyzed transformations
  作者：Juraj Galeta、Milan Potáček

  DOI：10.1016/j.molcata.2014.08.004

  日期：2014.12

  Superbasic properties of caged proton sponges (PSs) - substituted diazatetracyclo[4.4.0.1(3,10).1(5,8)] dodecanes (DTDs) - were utilized in Knoevenagel and Claisen-Schmidt condensations, the Pudovik reaction, and Michael addition. This investigation covers the influence of the solvent, reaction temperature, catalyst loadings as well as the electronic properties of substituents upon the reaction. Moreover, we provided an activity comparison between our new base and a well-known and commercially available proton sponge (R) (DMAN). The basicity (in MeCN) of our chosen DTD (pK(BH)(+) = 21.7 +/- 0.1) exceeded the prototypal PS - 1,8-bis(dimethylamino)naphthalene (DMAN, pK(BH)(+) = 18.6), by three orders of magnitude. We proved that DTDs are reasonably active species in monitored reactions, which is a consequence of a hydrogen bridge angle (approximate to 130 degrees) between the two nitrogen atoms and the captured proton. We present here syntheses of aminoindolizine, substituted 4H-chromene, and flavanones, and the unexpected formation of a bis-addition product formed after Michael addition, all under mild conditions. (C) 2014 Elsevier B.V. All rights reserved.
• FLITSCH, W.;KAHNER-GROENE, S., CHEM. BER., 1982, 115, N 3, 871-877
  作者：FLITSCH, W.、KAHNER-GROENE, S.

  DOI：——

  日期：——
• OXIDATION DYEING PROCESS USING A COMPOSITION COMPRISING AN AMINOBENZIMIDAZOLONE OXIDATION BASE AND A METAL CATALYST
  申请人：L'OREAL

  公开号：US20160136077A1

  公开（公告）日：2016-05-19

  The invention relates to a process for dyeing keratin fibres, comprising the use of one or more metal catalysts and of a composition (A) comprising: —one or more oxidizing agents, and —at least one aminobenzimidazole oxidation base of formula (I) in which the radicals R1 to R5 represent, independently of each other, a hydrogen atom; a halogen atom; a C1-C6 alkyl radical; a C1-C6 alkoxy radical; a C1-C6 dialkylamino radical; a carboxylic radical (—COOH); a sulfonic radical (—S03H); a phenyl radical; a sat orated or unsaturated 5- to 7-membered heterocyclic radical, comprising one or more heteroatoms chosen from N, O and S.