2-Butenoic acid, 3-[(1E)-(aminocarbonyl)azo]-, ethyl ester, (2E)- | 146000-77-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Butenoic acid, 3-[(1E)-(aminocarbonyl)azo]-, ethyl ester, (2E)-
• 英文别名: ethyl (E)-3-((E)-carbamoyldiazenyl)but-2-enoate；ethyl (E)-3-(carbamoyldiazenyl)but-2-enoate
• CAS: 146000-77-3
• 化学式: C₇H₁₁N₃O₃
• 分子量: 185.183
• InChiKey: DZKJGHCQIBAZFI-CMBSKSBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  94.11
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-Butenoic acid, 3-[(1E)-(aminocarbonyl)azo]-, ethyl ester, (2E)- 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 1.4h， 生成 ethyl 4-methyl-2-phenyl-Δ⁴-thiazoline-5-carboxylate
  参考文献：
  名称：

  Study of reactions between 1,2-diaza-1,3-butadienes and N,N′-diaryl- or N,N′-dialkylthioureas

  摘要：

  1,2-Diaza-1,3-butadienes react with N,N'-diarylthioureas to give 2-(arylimino)-2,3-dihydrothiazole derivatives, whereas with N,N'-dialkylthioureas to afford 5,5-disubstituted 3-alkyl-2-(alkylimino)-thiazdidin-4-one derivatives. Under basic conditions, these last products surprisingly give rise to 2-thioxo-1,3,7-triazaspiro[4.4]non-8-en-4-one and 5-oxo-4-(4-substituted 5-oxo-2-thioxoimidazolidin-4yl)-2,5-dihydro-1H-pyrazole derivatives. In acidic medium, 5,5-disubstituted 3-alkyl-2-(alkylimino)-thiazolidin-4-ones are converted into 2-(alkylimino)-1-thia-3,7-diazaspiro[4.4]non-7-en-4-ones. X-Ray crystal structures of two products were determined. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00827-3

文献信息

• Regioselective Synthesis of Stable 2-(Trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ols and Derived Fluorinated Heterocycles
  作者：Orazio A. Attanasi、Paolino Filippone、Barbara Guidi、Fabio Mantellini、Stefania Santeusanio

  DOI：10.1055/s-2001-17510

  日期：——

  1-aminopyrrole derivatives in good to excellent yields. The reaction of 2(trifluoromethyl)-2,3-dihydro-1H-pyrrol-2-ol derivative with 2-haloketone affords fluorinated furo[2,3-b]pyrroline derivative, while that of diethyl 1-[(anilinocarbonyl)amino]-2-methyl-5-(trifluoromethyl)-1H-pyrrole-3,4-dicarboxylate with hydrazine hydrate affords fluorinated pyrrolo[3,4-d]pyridazindione derivative.

  Synthesis 2001, No. 12, 25 09 2001。文章标识符：1437-210X,E;2001,0,12,1837,1845,ftx,en;E03501ss.pdf。© Georg Thieme Verlag Stuttgart · 纽约 ISSN 0039-7881 摘要：1,2-二氮杂-1,3-丁二烯与三氟甲基化的 b-二羰基化合物区域选择性反应生成稳定的 2-(三氟甲基)-2,3-二氢-1H- pyrrol-2-ol 衍生物，在用三氟甲磺酸酐或非均相催化剂处理后，以良好至优异的产率产生氟化 1-氨基吡咯衍生物。2(三氟甲基)-2,3-二氢-1H-吡咯-2-醇衍生物与2-卤代酮反应得到氟化呋喃[2,3-b]吡咯啉衍生物，而二乙基1-[(苯胺羰基)氨基]-2-methyl-5-(trifluoromethyl)-1H-pyrrole-3,4-dicarboxylate
• Conjugated Azoalkenes; Part XV: Facile and Direct Synthesis of New 3-Phosphonopyrrole and 3a-Phosphonopyrrolo[2,3-<i>b</i>]pyrrole Derivatives
  作者：Orazio A. Attanasi、Paolino Filippone、Daniela Giovagnoli、Amedeo Mei

  DOI：10.1055/s-1994-25434

  日期：——

  1-Amino-3-phosphonopyrroles were prepared by direct reaction between conjugated azoalkenes and dimethyl (2-oxopropyl)phosphonate while the treatment of conjugated azoalkenes with diethyl cyanomethylphosphonate gives 1,2-diamino-3-phosphonopyrroles or 3a-phosphono-1,3a,6,6a-tetrahydropyrrolo[2,3-b]pyrroles, depending on the molar ratios of the reagents.

  通过直接反应，将共轭偶氮烯与二甲基（2-氧代丙基）膦酸酯进行反应，制备了1-氨基-3-膦基吡咯。而共轭偶氮烯与二乙基氰甲基膦酸酯反应，则根据反应物的摩尔比，生成1,2-二氨基-3-膦基吡咯或3a-膦基-1,3a,6,6a-四氢吡咯并[2,3-b]吡咯。
• Study of the reaction between conjugated azoalkenes and α-unsubstituted- or α-substituted-β-dicarboxylate derivatives: an improved preparation of unknown polyfunctionalized 1-amino-1<i>H</i>-pyrrol-2(3<i>H</i>)-ones
  作者：Orazio A. Attanasi、Lucia De Crescentini、Franco Serra-Zanetti、Elisabetta Foresti

  DOI：10.1139/v94-293

  日期：1994.11.1

  In the presence of sodium methoxide in catalytic amounts, conjugated azoalkenes easily react with α-unsubstituted-or α-sub-stituted-β-dicarboxylate derivatives to give at first hydrazonic derivatives, by 1,4-conjugate addition, and, by increasing sodium methoxide up to stoichiometric amounts, new polyfunctionalized 1-amino-1H-pyrrol-2(3H)-ones.

  在存在催化量的甲氧基钠的情况下，共轭偶氮烯很容易与α-未取代或α-取代的β-二羧酸酯衍生物反应，首先生成肼酮衍生物，通过1,4-共轭加成，然后通过增加甲氧基钠至化学计量量，生成新的多官能基化的1-氨基-1H-吡咯-2(3H)-酮。
• Synthesis, reaction, theoretical calculation, NMR study and X-ray crystal structure of 1-substituted and 1-unsubstituted 1H-pyrazol-5(2H)-ones
  作者：Orazio A. Attanasi、Lucia De Crescentini、Paolino Filippone、Elisabetta Foresti、Roberta Galezzi、Ion Ghiviriga、Alan R. Katritzky

  DOI：10.1016/s0040-4020(97)00217-2

  日期：1997.4

  studied by molecular mechanics calculations, as well as deuterium induced shifts (DIS) on 13C chemical shifts, and tentative conclusion was drawn about their tautomerism and conformations. X-Ray crystal structure determinations of 1-(aminocarbonyl)-3-methyl-4-methoxy-1H-pyrazol-5(2H)-one 4e and 3-methyl-4-methoxy-1H-pyrazol-5(2H)-one 5a demonstrated that both molecules exist in the crystal exclusively

  通过共轭偶氮烯烃与醇，硫醇和酚的反应已经制备了1-取代的4-烷氧基-，4-烷硫基和4-芳氧基-1 H-吡唑-5（2 H）-。在某些情况下，分离出中间，而在其他情况下，则一步一步获得产物。通过在回流下甲醇裂解相应的1-取代的衍生物来制备1-未取代的4-烷氧基-，4-烷硫基-和4-芳氧基-1 H-吡唑-5（2 H）-。通过分子力学计算研究了其中一些化合物，以及13位的氘诱导的位移（DIS）。C化学位移，并就其互变异构和构象作了初步结论。1-（氨基羰基）-3-甲基-4-甲氧基-1 H-吡唑-5（2 H）-one 4e和3-甲基-4-甲氧基-1 H-吡唑-5（）的X射线晶体结构测定2 H）-1 5a证明两个分子仅以HN-CO互变异构形式存在于晶体中。一些吡唑啉酮和羟基吡唑中先前报道的一些结构分配已得到纠正。
• Synthesis of 1-Substituted and 1-Unsubstituted 4-Sulfonamid0-1H-pyrazol-5(2H)-ones
  作者：Antonio Arcadi、Orazio A. Attanasi、Lucia De Crescentini、Elisabetta Rossi、Franco Serra-Zanetti

  DOI：10.1055/s-1996-4231

  日期：1996.4

  4-Sulfonamido-1H-pyrazol-5(2H)-ones bearing different substituent groups on the nitrogen atom in position 1 were easily obtained by reaction of conjugated azoalkenes with sulfonamides under mild conditions. 1-Unsubstituted title compounds were smoothly obtained by solvolytic cleavage of the substituent groups in methanol under reflux.

  在温和条件下，通过共轭偶氮烯与磺胺的反应，可轻易制备出1位氮原子上带有不同取代基团的4-磺胺基-1H-吡唑-5(2H)-酮类化合物。未取代的标题化合物则通过甲醇回流条件下的溶剂解裂解取代基团，顺利得到。