2-(2,4,5-trichloro-3,6-dioxocyclohexa-1,4-dien-1-yl)malononitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,4,5-trichloro-3,6-dioxocyclohexa-1,4-dien-1-yl)malononitrile
• 英文别名: 2-(2,4,5-Trichloro-3,6-dioxocyclohexa-1,4-dien-1-yl)propanedinitrile；2-(2,4,5-trichloro-3,6-dioxocyclohexa-1,4-dien-1-yl)propanedinitrile
• 化学式: C₉HCl₃N₂O₂
• 分子量: 275.478
• InChiKey: NUADPWVHNDASJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氯苯醌 、 丙二腈 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 2-(2,4,5-trichloro-3,6-dioxocyclohexa-1,4-dien-1-yl)malononitrile
  参考文献：
  名称：

  One-pot synthesis and negative ion mass spectrometric investigation of a densely functionalized cinnoline

  摘要：

  Known, densely substituted 3-amino-5,7,8-trichloro-6-hydroxycinnoline-4-carbonitrile was synthesized using a one pot synthetic protocol under base-mediated conditions in a polar medium. Condensation of excess malononitrile with chloranil in ethanol at reflux gave quinone methide-2-(2,4,5-trichloro-3-hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene)malononitrile which was isolated as the triethylamine salt. This represents an atom efficient, simple, and effective procedure for the preparation of a highly substituted cinnolines that may serve as relay materials for antimalarial prototypes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.10.104

文献信息

• One-pot synthesis and negative ion mass spectrometric investigation of a densely functionalized cinnoline
  作者：Daniel J. Lambert、Nigam Parikh、Stephen J. Messham、Giles Edwards、Hieu van Truong、Nicola M. Dempster、Michael G.B. Drew、Lutfun Nahar、Satyajit D. Sarker、Fyaz M.D. Ismail

  DOI：10.1016/j.tetlet.2015.10.104

  日期：2015.12

  Known, densely substituted 3-amino-5,7,8-trichloro-6-hydroxycinnoline-4-carbonitrile was synthesized using a one pot synthetic protocol under base-mediated conditions in a polar medium. Condensation of excess malononitrile with chloranil in ethanol at reflux gave quinone methide-2-(2,4,5-trichloro-3-hydroxy-6-oxocyclohexa-2,4-dien-1-ylidene)malononitrile which was isolated as the triethylamine salt. This represents an atom efficient, simple, and effective procedure for the preparation of a highly substituted cinnolines that may serve as relay materials for antimalarial prototypes. (C) 2015 Elsevier Ltd. All rights reserved.