tert-butyl 2-(4-isopropoxy-4-oxobut-2-en-2-yl)diazene-1-carboxylate | 228716-42-5

• 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: tert-butyl 2-(4-isopropoxy-4-oxobut-2-en-2-yl)diazene-1-carboxylate
• CAS: 228716-42-5
• 化学式: C₁₂H₂₀N₂O₄
• 分子量: 256.302
• InChiKey: LKKICOZAXCPEIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.32
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(4-isopropoxy-4-oxobut-2-en-2-yl)diazene-1-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.2h， 生成 tert-butyl 2-(2-{5-[2-[(tert-butoxycarbonyl)hydrazono]-1-(ethoxycarbonyl)propyl]-1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl}-3-isopropoxy-1-methyl-3-oxopropylidene)hydrazine-1-carboxylate
  参考文献：
  名称：

  Double Michael addition/aza-cyclization: a valuable sequence for the construction of symmetrical and unsymmetrical spirobarbiturate-pyridines

  摘要：

  A simple one-pot procedure for the preparation of symmetrical bis-hydrazone functionalized barbiturates, and a step-by step sequence for the synthesis of analogous unsymmetrical derivatives were developed. Their treatment in acid conditions furnish the symmetrical- and unsymmetrical-spirobarbiturate-pyridines, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.04.004

文献信息

• FeCl ₃ ‐Catalyzed Formal [3+2] Cyclodimerization of 4‐Carbonyl‐1,2‐diaza‐1,3‐dienes
  作者：Giacomo Mari、Matteo Corrieri、Lucia De Crescentini、Gianfranco Favi、Stefania Santeusanio、Fabio Mantellini

  DOI：10.1002/ejoc.202101046

  日期：2021.10.7

  An 1,2-diaza-1,3-diene's cyclodimerization that provides symmetrical fully substituted 1-amino pyrroles through an unusual formal [3+2] reaction is investigated. The study has demonstrated that the presence of electron withdrawing groups on the terminal carbon atom of the azo-ene system is crucial for the success of the reaction. The synthesis occurs with complete regioselectivity and requires a very

  研究了 1,2-二氮杂-1,3-二烯的环二聚反应，通过不寻常的正式 [3+2] 反应提供对称的完全取代的 1-氨基吡咯。研究表明，偶氮烯体系末端碳原子上吸电子基团的存在对反应的成功至关重要。该合成具有完全的区域选择性，需要非常简单的后处理程序。
• Synthesis of novel symmetrical 2-oxo-spiro[indole-3,4′-pyridines] by a reaction of oxindoles with 1,2-diaza-1,3-dienes
  作者：Orazio A. Attanasi、Linda A. Campisi、Lucia De Crescentini、Gianfranco Favi、Fabio Mantellini

  DOI：10.1039/c4ob01959h

  日期：——

  Synthesis of symmetrical 2-oxo-spiro[indole-3,4′-pyridines]: a novel example of spirocyclic oxindoles bearing a quaternary centre at the 3-position.

  对称2-氧代螺[indole-3,4′-吡啶]的合成：一种在3位上带有季铵中心的螺环氧吲哚的新例子。
• Zn(II)-Catalyzed Addition of Aromatic/Heteroaromatic C(sp²)–H to Azoalkenes: A Polarity-Reversed Arylation of Carbonyl Compounds
  作者：Cecilia Ciccolini、Lucia De Crescentini、Fabio Mantellini、Stefania Santeusanio、Gianfranco Favi

  DOI：10.1021/acs.orglett.9b01628

  日期：2019.6.7

  An umpolung α-(hetero)arylation strategy that involves the Michael-type reaction between electron-rich (hetero)aromatic substrates and azoalkenes is developed. The reaction proceeds under very mild conditions at room temperature and in the presence of inexpensive, nontoxic ZnCl2 catalyst to provide access to otherwise inaccessible hydrazone structures. Subsequent hydrolysis of these latter to ketones

  提出了一种涉及富电子（杂）芳族底物与偶氮烯烃之间的迈克尔型反应的α-（杂）芳基化反应策略。该反应在非常温和的条件下，在室温下，在廉价，无毒的ZnCl 2催化剂的存在下进行，以提供通向否则无法接近的结构的通道。这些后者随后水解为酮，以及其他有价值的合成转化为各种杂环支架，证明了该方案的实用性。
• Synthesis of Azacarbolines via PhIO₂-Promoted Intramolecular Oxidative Cyclization of α-Indolylhydrazones
  作者：Matteo Corrieri、Lucia De Crescentini、Fabio Mantellini、Giacomo Mari、Stefania Santeusanio、Gianfranco Favi

  DOI：10.1021/acs.joc.1c02217

  日期：2021.12.17

  An unprecedented synthesis of polysubstituted indole-fused pyridazines (azacarbolines) from α-indolylhydrazones under oxidative conditions using a combination of iodylbenzene (PhIO2) and trifluoroacetic acid (TFA) has been developed. This transformation is conducted without the need for transition metals, harsh conditions, or an inert atmosphere.

  已经开发了在氧化条件下使用碘基苯 (PhIO 2 ) 和三氟乙酸 (TFA) 的组合从 α-吲哚腙合成多取代吲哚稠合哒嗪 (氮杂咔啉) 的前所未有的方法。这种转变无需过渡金属、恶劣条件或惰性气氛即可进行。
• Metal and Oxidant-Free Brønsted Acid-Mediated Cascade Reaction to Substituted Benzofurans
  作者：Giacomo Mari、Cecilia Ciccolini、Lucia De Crescentini、Gianfranco Favi、Stefania Santeusanio、Michele Mancinelli、Fabio Mantellini

  DOI：10.1021/acs.joc.9b01363

  日期：2019.9.6

  Substituted hydroxy-benzofurans are easily accessible by treatment of resorcinols and 1,2-diaza-1,3-dienes (DDs) under acidic conditions. The reaction happens through an uncommon Michael reaction between aromatic derivatives as aromatic C(sp2)–H nucleophiles and DDs as acceptors. Also, the behavior of different phenols and 2-naphthol was investigated.

  通过在酸性条件下处理间苯二酚和1,2-二氮杂-1,3-二烯（DDs），可以轻松获得取代的羟基苯并呋喃。该反应通过芳香族衍生物（作为芳香族C（sp 2）–H亲核体）和DDs作为受体之间的罕见迈克尔反应而发生。此外，还研究了不同酚和2-萘酚的行为。