ethyl 2-(carbamoyldiazenyl)cyclooct-1-ene-1-carboxylate | 1025066-05-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(carbamoyldiazenyl)cyclooct-1-ene-1-carboxylate
• CAS: 1025066-05-0
• 化学式: C₁₂H₁₉N₃O₃
• 分子量: 253.301
• InChiKey: VYFLDGZYKCRYJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1-甲基吲哚 、 ethyl 2-(carbamoyldiazenyl)cyclooct-1-ene-1-carboxylate 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到(8aS*,13bR*,13cR*)-ethyl 8-carbamoy l -9-methyl-2,3,4,5,6,8,8a,9,13b,13c-decahydro-1H-cycloocta[5,6]pyridazino-[3,4-b]indole-13c-carboxylate
  参考文献：
  名称：

  Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch

  摘要：

  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.

  DOI：

  10.1021/acs.joc.0c01489

文献信息

• Divergent base-induced reactivity of cycloalkenyl-1-diazenes
  作者：Orazio A. Attanasi、Stefano Berretta、Lucia De Crescentini、Gianfranco Favi、Paolino Filippone、Gianluca Giorgi、Fabio Mantellini

  DOI：10.1016/j.tet.2010.06.061

  日期：2010.8

  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.