diallyl diazenedicarboxylate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diallyl diazenedicarboxylate
• 英文别名: diallyl azodicarboxylate；prop-2-enyl N-prop-2-enoxycarbonyliminocarbamate
• 化学式: C₈H₁₀N₂O₄
• 分子量: 198.178
• InChiKey: IAMJNZFWTVSZEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻氯苯酚 、 diallyl diazenedicarboxylate 在 氯化锆(IV) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以78%的产率得到diallyl 1-(3-chloro-4-hydroxyphenyl)-1,2-hydrazinedicarboxylate
  参考文献：
  名称：

  Electrophilic Amination of 4-Fluorophenol with Diazenes:  A Complete Removal of the Fluorine Atom

  摘要：

  The electrophilic amination of 2-fluorophenol, 4-fluorophenol, and 2-chlorophenol was observed to occur as a result of their treatment with diazenes 1-4 under mild reaction conditions in the presence of ZrCl4. The products originating from the 2-fluorophenol or 2-chlorophenol can be considered as "normal" products of amination. On the other hand, the 2-chloro-4-amino-substituted phenols obtained from the 4-fluorophenol seem to be formed in a process that involves an ipso amination, the complete removal of the fluorine atom, and the introduction of the chlorine atom.

  DOI：

  10.1021/jo035856b
• 作为产物：
  描述：

  氯甲酸烯丙酯 在 一水合肼 、 碘苯二乙酸 作用下， 生成 diallyl diazenedicarboxylate
  参考文献：
  名称：

  An anti-tetraamination of a 1,3-diene unit via cascade annulations of the azulenone scaffold with dicarbonyl azo-compounds

  摘要：

  通过(i)烯、(ii)[6 + 2]-环加成和(iii)杂共轭加成反应，在氮酮支架上实现了 C-N 键的密集和立体控制整合，从而形成拓扑结构复杂的双桥骨架。

  DOI：

  10.1039/b926676c

文献信息

• Generation of Anti-trypanosomal Agents through Concise Synthesis and Structural Diversification of Sesquiterpene Analogues
  作者：Hiroki Oguri、Takahisa Hiruma、Yutaka Yamagishi、Hideaki Oikawa、Aki Ishiyama、Kazuhiko Otoguro、Haruki Yamada、Satoshi O̅mura

  DOI：10.1021/ja200374q

  日期：2011.5.11

  the canonical sets, as well as regio- and stereoisomers of the tricyclic dienes, allowed generation of several anti-trypanosomal agents defining the three-dimensional shape of the pharmacophore. The candidate tricyclic dienes were selected by primary screenings and further subjected to installation of a peroxide bridge, which generated artemisinin analogues that exhibited potent in vitro anti-trypanosomal

  为了获得高质量的小分子库来筛选以人类非洲锥虫病为代表的被忽视疾病的主要候选者，我们试图开发一种合成过程，该过程将产生与一系列具有理想生物活性的天然产物相关的环状支架集合。通过提取包括青蒿素、anthecularin 和 transtaganolides 在内的几种倍半萜的共同结构特征，我们设计了六种具有系统结构变化的支架，包括 sp(3) 环连接上的三种立体化学关系和两种不同的三环阵列构架。利用多功能流形的二炔的模块化和立体发散组装产生了一系列环化前体。采用串联闭环复分解反应的二炔的发散环化覆盖了环化前体的不同反应性，导致三环支架的六个标准组结合了二烯基团。筛选标准集的锥虫活性，以及​​三环二烯的区域异构体和立体异构体，允许产生定义药效团三维形状的几种抗锥虫药物。通过初步筛选选择候选三环二烯，并进一步安装过氧化物桥，产生的青蒿素类似物表现出有效的体外抗锥虫活性，与青蒿素和批准的药物苏拉明和依氟鸟氨酸相当甚至更好。
• Asymmetric Dearomatization of β-Naphthols through an Amination Reaction Catalyzed by a Chiral Phosphoric Acid
  作者：Shou-Guo Wang、Qin Yin、Chun-Xiang Zhuo、Shu-Li You

  DOI：10.1002/anie.201409756

  日期：2014.11.20

  A highly efficient catalytic asymmetric dearomatization of naphthols by means of an electrophilic amination reaction catalyzed by chiral phosphoric acid is presented. This protocol provides a facile access to functionalized β‐naphthalenone compounds with a chiral quaternary carbon center in excellent yields and enantioselectivity (up to 99 % yield, up to 96 % ee).

  提出了通过手性磷酸催化的亲电胺化反应使萘酚高效催化不对称脱芳香化反应。该方案可轻松获得具有手性季碳中心的功能化β-萘酮化合物，且收率和对映选择性极好（高达99％的收率，高达96％的 ee）。
• Electrophilic Amination of 4-Fluorophenol with Diazenes:  A Complete Removal of the Fluorine Atom
  作者：Sergeja Bombek、Franc Požgan、Marijan Kočevar、Slovenko Polanc

  DOI：10.1021/jo035856b

  日期：2004.3.1

  The electrophilic amination of 2-fluorophenol, 4-fluorophenol, and 2-chlorophenol was observed to occur as a result of their treatment with diazenes 1-4 under mild reaction conditions in the presence of ZrCl4. The products originating from the 2-fluorophenol or 2-chlorophenol can be considered as "normal" products of amination. On the other hand, the 2-chloro-4-amino-substituted phenols obtained from the 4-fluorophenol seem to be formed in a process that involves an ipso amination, the complete removal of the fluorine atom, and the introduction of the chlorine atom.
• An anti-tetraamination of a 1,3-diene unit via cascade annulations of the azulenone scaffold with dicarbonyl azo-compounds
  作者：Yuhei Ishigaki、Velisoju Mahendar、Hiroki Oguri、Hideaki Oikawa

  DOI：10.1039/b926676c

  日期：——

  Dense and stereo-controlled integrations of C–N bonds on the azulenone scaffold are achieved by sequential (i) ene, (ii) [6 + 2]-cycloaddition, and (iii) hetero-conjugate addition reactions leading to a topologically complex bis-bridged skeleton.

  通过(i)烯、(ii)[6 + 2]-环加成和(iii)杂共轭加成反应，在氮酮支架上实现了 C-N 键的密集和立体控制整合，从而形成拓扑结构复杂的双桥骨架。