2-[4,5-bis(2-cyanoethylthio)-1,3-dithiole-2-ylidene]-4,6-dihydro-N-[2-(tetrahydroprpyran-2-oxy)ethyl]-(1,3)-dithiolo[4,5-c]pyrrole | 300766-29-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-[4,5-bis(2-cyanoethylthio)-1,3-dithiole-2-ylidene]-4,6-dihydro-N-[2-(tetrahydroprpyran-2-oxy)ethyl]-(1,3)-dithiolo[4,5-c]pyrrole
• 英文别名: 3-[[5-(2-Cyanoethylsulfanyl)-2-[5-[2-(oxan-2-yloxy)ethyl]-4,6-dihydro-[1,3]dithiolo[4,5-c]pyrrol-2-ylidene]-1,3-dithiol-4-yl]sulfanyl]propanenitrile
• CAS: 300766-29-4
• 化学式: C₂₁H₂₅N₃O₂S₆
• 分子量: 543.844
• InChiKey: PJZSBPAVANNDPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-[4,5-bis(2-cyanoethylthio)-1,3-dithiole-2-ylidene]-4,6-dihydro-N-[2-(tetrahydroprpyran-2-oxy)ethyl]-(1,3)-dithiolo[4,5-c]pyrrole 在 盐酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 16.0h， 以83%的产率得到2-[4,5-bis(2-cyanoethylthio)-1,3-dithiole-2-ylidene]-4,6-dihydro-N-(2-hydroxyethyl)-(1,3)-dithiolo[4,5-c]pyrrole
  参考文献：
  名称：

  Pyrrolo-Annelated Tetrathiafulvalenes:  The Parent Systems

  摘要：

  The synthesis of a number pyrrolo-annelated tetrathiafulvalenes, including the parent bis(pyrrolo-[3,4-d])tetrathiafulvalene (7) is decribed. Starting from readily available 4,5-bis(bromomethyl)-1,3-dithiole-2-thione (14) and sodium tosylamide, the parent 7 and the asymmetric monopyrrolo tetrathiafulvalenes 23a;b were prepared in good yields via a nonclassical and simple pyrrole synthesis. Furthermore, a series of asymmetrical N-alkylated monopyrrolo/monodihydropyrrolotetrathiafulvalenes was prepared starting from primary amines and 14. A detailed study of the fundamental redox behavior of this class of heterocycles is reported. NMR spectroscopy, cyclic voltammetry, and PM3 MO calculations revealed that the pyrrolo-annelated tetrathiafulvalenes have highly extended pi-surfaces. The X-ray crystallographic analyses of the monopyrrolo tetrathiafulvalenes 22b and 24b, together with preliminary formation of a charge-transfer complex between the parent donor 7 and TCNQ, are also reported.

  DOI：

  10.1021/jo000742a
• 作为产物：
  描述：

  1,3-二噻唑-2-硫酮,4,5-二(溴甲基)- 在 caesium carbonate 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 3.0h， 生成 2-[4,5-bis(2-cyanoethylthio)-1,3-dithiole-2-ylidene]-4,6-dihydro-N-[2-(tetrahydroprpyran-2-oxy)ethyl]-(1,3)-dithiolo[4,5-c]pyrrole
  参考文献：
  名称：

  Pyrrolo-Annelated Tetrathiafulvalenes:  The Parent Systems

  摘要：

  The synthesis of a number pyrrolo-annelated tetrathiafulvalenes, including the parent bis(pyrrolo-[3,4-d])tetrathiafulvalene (7) is decribed. Starting from readily available 4,5-bis(bromomethyl)-1,3-dithiole-2-thione (14) and sodium tosylamide, the parent 7 and the asymmetric monopyrrolo tetrathiafulvalenes 23a;b were prepared in good yields via a nonclassical and simple pyrrole synthesis. Furthermore, a series of asymmetrical N-alkylated monopyrrolo/monodihydropyrrolotetrathiafulvalenes was prepared starting from primary amines and 14. A detailed study of the fundamental redox behavior of this class of heterocycles is reported. NMR spectroscopy, cyclic voltammetry, and PM3 MO calculations revealed that the pyrrolo-annelated tetrathiafulvalenes have highly extended pi-surfaces. The X-ray crystallographic analyses of the monopyrrolo tetrathiafulvalenes 22b and 24b, together with preliminary formation of a charge-transfer complex between the parent donor 7 and TCNQ, are also reported.

  DOI：

  10.1021/jo000742a

文献信息

• Pyrrolo-Annelated Tetrathiafulvalenes:  The Parent Systems
  作者：Jan Oskar Jeppesen、Kazuo Takimiya、Frank Jensen、Thomas Brimert、Kent Nielsen、Niels Thorup、Jan Becher

  DOI：10.1021/jo000742a

  日期：2000.9.1

  The synthesis of a number pyrrolo-annelated tetrathiafulvalenes, including the parent bis(pyrrolo-[3,4-d])tetrathiafulvalene (7) is decribed. Starting from readily available 4,5-bis(bromomethyl)-1,3-dithiole-2-thione (14) and sodium tosylamide, the parent 7 and the asymmetric monopyrrolo tetrathiafulvalenes 23a;b were prepared in good yields via a nonclassical and simple pyrrole synthesis. Furthermore, a series of asymmetrical N-alkylated monopyrrolo/monodihydropyrrolotetrathiafulvalenes was prepared starting from primary amines and 14. A detailed study of the fundamental redox behavior of this class of heterocycles is reported. NMR spectroscopy, cyclic voltammetry, and PM3 MO calculations revealed that the pyrrolo-annelated tetrathiafulvalenes have highly extended pi-surfaces. The X-ray crystallographic analyses of the monopyrrolo tetrathiafulvalenes 22b and 24b, together with preliminary formation of a charge-transfer complex between the parent donor 7 and TCNQ, are also reported.