Ethyl 2-(phenylcarbamoyldiazenyl)cyclohexene-1-carboxylate | 1025066-00-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 2-(phenylcarbamoyldiazenyl)cyclohexene-1-carboxylate
• CAS: 1025066-00-5
• 化学式: C₁₆H₁₉N₃O₃
• 分子量: 301.345
• InChiKey: GMBMLAFRHAIZIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  80.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(phenylcarbamoyldiazenyl)cyclohexene-1-carboxylate 、 乙酰丙酮苄酯 在 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到4-benzyl 4a-ethyl 2-(anilinocarbonyl)-3-hydroxy-3-methyl-3,4,5,6,7,8-hexahydrocinnoline-4-4a(2H)-dicarboxylate
  参考文献：
  名称：

  Divergent base-induced reactivity of cycloalkenyl-1-diazenes

  摘要：

  The different base-promoted regioselectivities of the ring closure processes in the reactions between cycloalkenyl-1-diazenes and beta-ketoesters are investigated. Under the appropriate conditions it is possible to turn the synthesis towards cycloalkenyliden-pyrroles or functionalized 3-hydroxy-hydrocinnolines. The aromatization procedure of the heteroring counterpart of the 3-hydroxy-hydrocinnolines is also reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.061

文献信息

• 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。
• Efficient, High-Yield, One-Pot Protocol for the Synthesis of 1,2,4-Oxadiazine Derivatives
  作者：Stefania Santeusanio、Orazio Attanasi、Livius Cotarca、Gianfranco Favi、Paolino Filippone、Francesca Perrulli

  DOI：10.1055/s-0029-1217326

  日期：——

  1,2-Diaza-1,3-dienes easily react as Michael acceptors with arylamidoximes in a one-pot, high-yield heterocyclization process. Depending on the linear or cyclic structure of the ene mojety, 1,2,4-oxadiazin-5-ones or spiro cycloalkyl-1,2,4-oxadiazin-5-one derivatives can be directly obtained.

  作为迈克尔受体，1,2-二氮杂-1,3-二烯很容易与芳基酰胺肟发生反应，实现一锅式高产杂环化过程。根据烯烃的线性或环状结构，可直接获得 1,2,4-恶二嗪-5-酮或螺环烷基-1,2,4-恶二嗪-5-酮衍生物。
• A facile protocol for the preparation of 2-carboxylated thieno [2,3-<i>b</i>] indoles: a <i>de novo</i> access to alkaloid thienodolin
  作者：Giacomo Mari、Lucia De Crescentini、Gianfranco Favi、Stefania Santeusanio、Fabio Mantellini

  DOI：10.1039/d2ob00440b

  日期：——

  3-dienes and indoline 2-thione and requires mild reaction conditions. Furthermore, the easy work-up required makes this method amenable for a one-pot approach as demonstrated in the preparation of thienodolin, a natural product isolated from Streptomyces albogriseolus that exhibits valuable biological properties.

  已成功开发出一种无金属策略，可替代已知的复杂环加成反应，生成 2-羧化噻吩并 [2,3- b ] 吲哚衍生物。新方法涉及作为起始材料易于获得的 1,2-二氮杂-1,3-二烯和二氢吲哚 2-硫酮，并且需要温和的反应条件。此外，所需的简单后处理使该方法适用于一锅法，如噻吩多林的制备所证明的那样，噻吩多林是一种从白灰链霉菌中分离出来的天然产物，具有有价值的生物学特性。
• Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch
  作者：Cecilia Ciccolini、Giacomo Mari、Francesco G. Gatti、Giuseppe Gatti、Gianluca Giorgi、Fabio Mantellini、Gianfranco Favi

  DOI：10.1021/acs.joc.0c01489

  日期：2020.9.4

  Zn(II)-catalyzed divergent synthesis of functionalized polycyclic indolines through formal [3 + 2] and [4 + 2] cycloadditions of indoles with 1,2-diaza-1,3-dienes (DDs) is reported. The nature and type of substituents of substrates are found to act as a chemical switch to trigger two distinct reaction pathways and to obtain two different types of products upon the influence of the same catalyst. The mechanism of both [4 + 2] and [3 + 2] cycloadditions was investigated and fully rationalized by density functional theory (DFT) calculations.