2-formyl-9,10-bis(dicyanomethylene)anthraquinone oxime | 301847-98-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-formyl-9,10-bis(dicyanomethylene)anthraquinone oxime
• 英文别名: 2-[10-(dicyanomethylidene)-3-(hydroxyiminomethyl)anthracen-9-ylidene]propanedinitrile
• CAS: 301847-98-3
• 化学式: C₂₁H₉N₅O
• 分子量: 347.335
• InChiKey: XEWKCEZQYOQVID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  127.75
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-formyl-9,10-bis(dicyanomethylene)anthraquinone oxime 在 吡啶 、 N-氯代丁二酰亚胺 作用下， 以 氯仿 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  [60]Fullerene Adducts with Improved Electron Acceptor Properties

  摘要：

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.

  DOI：

  10.1021/jo0003753
• 作为产物：
  描述：

  2-羟甲基蒽醌 在 吡啶 、 盐酸羟胺 、 四氯化钛 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 12.5h， 生成 2-formyl-9,10-bis(dicyanomethylene)anthraquinone oxime
  参考文献：
  名称：

  [60]Fullerene Adducts with Improved Electron Acceptor Properties

  摘要：

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.

  DOI：

  10.1021/jo0003753

文献信息

• [60]Fullerene Adducts with Improved Electron Acceptor Properties
  作者：Beatriz M. Illescas、Nazario Martín

  DOI：10.1021/jo0003753

  日期：2000.9.1

  The synthesis of C-60-based dyads in which the C-60 core is covalently attached to a strong electron acceptor moiety such as quinones, TCNQ or DCNQI derivatives, has been carried out by 1,3-dipolar cycloaddition of "in situ" generated azomethyne ylides or nitrile oxides to C-60. As expected, the obtained pyrrolidino[3',4':1,2][60]fullerenes exhibit reduction potentials of the C-60 framework which are cathodically shifted in comparison with the parent C-60. In contrast, isoxazolo[4',5':1,2][60]fullerenes show reduction waves for the fullerene core that are anodically shifted in comparison with the parent C-60, which indicates that they are remarkably stronger accepters than C-60. The electron acceptor organic addend also undergoes an anodic shift due to the electronic interaction with the C-60 moiety. The molecular geometry of pyrrolidinofullerenes has been calculated at the semiempirical PM3 level and reveals a highly distorted geometry for the acceptor moiety in compound 13, and a most stable conformation in which both dicyanomethylene units are far away from the C-60 surface.