1,1,4,4-Tetrakis(piperidino)-but-2-en-1,4-diylium-2,3-dithiolat | 181526-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,1,4,4-Tetrakis(piperidino)-but-2-en-1,4-diylium-2,3-dithiolat
• CAS: 181526-97-6
• 化学式: C₂₄H₄₀N₄S₂
• 分子量: 448.74
• InChiKey: ZWCDEFWEESZLND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  30.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  12.5
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 1,1,4,4-Tetrakis(piperidino)-but-2-en-1,4-diylium-2,3-dithiolat 以 乙腈 为溶剂， 反应 24.0h， 以74%的产率得到(E)-3,3,3',3'-Tetra-piperidin-1-yl-3H,3'H-[2,2']bithiophenylidene-4,5,4',5'-tetracarboxylic acid tetramethyl ester
  参考文献：
  名称：

  Orthoamide. IL. Umsetzungen von Orthoamid-Derivaten mit Schwefel und Selen, Synthesen von 1,3-Thiazol- und 1,3-Selenazolderivaten

  摘要：

  N,N-Dimethylformamide acetal reacts with elemental selenium to give a mixture of selenocarbonic acid derivatives 2 and 3, which can be converted to the pure N,N-dimethylcarbamidic acid Se-methylester 2 by treatment with methyl iodide. Analogously from the orthoformic acid derivatives 5 and 6 and selenium the N,N,N',N'-tetramethyl-selenurea 7 can be prepared. In the reaction of 12 with elemental sulfur and selenium the amidines 14 and 15, respectively, are formed. By treatment of 14 and 15 with alpha-halogenated carbonyl compounds and triethylamine the 1,3-thiazoles 18 and 1,3-selenazoles 19 can be prepared. The synthesis of the propynoic acid orthoamide 26b is described. 26b reacts with the guanidinium salt 24b to give the bis-orthoamide of butynedioic acid 20b. Other orthoamides of butynedioic acid 20b-20e can be synthesized from the orthoamide 20a by transamination. The thiolation of the orthoamides affords the bis-amidinium-dithiolates 21a-c, which can be alkylated to give the bis-amidinium salts 27. By treatment with alpha-halogene carbonyl compounds and triethylamine the dithiolates 21a-e are cyclized to give thieno [3,2b] thiophenes 28a-n. The quadrupoles 21 undergo cycloadditions with dimethyl-butynedioate which afford the bis(3H-thiophene-2 ylidenes) 29a-c. Treatment of 29a with methyl tosylate gives rise to the dithiophene 30a. The dithiophene 30b can be obtained by heating 21b with dimethylbutynedionate.

  DOI：

  10.1002/prac.19963380180
• 作为产物：
  描述：

  1-[1,1,4,4,4-Penta(piperidin-1-yl)but-2-ynyl]piperidine 在 sulfur 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以87%的产率得到1,1,4,4-Tetrakis(piperidino)-but-2-en-1,4-diylium-2,3-dithiolat
  参考文献：
  名称：

  Orthoamide. IL. Umsetzungen von Orthoamid-Derivaten mit Schwefel und Selen, Synthesen von 1,3-Thiazol- und 1,3-Selenazolderivaten

  摘要：

  N,N-Dimethylformamide acetal reacts with elemental selenium to give a mixture of selenocarbonic acid derivatives 2 and 3, which can be converted to the pure N,N-dimethylcarbamidic acid Se-methylester 2 by treatment with methyl iodide. Analogously from the orthoformic acid derivatives 5 and 6 and selenium the N,N,N',N'-tetramethyl-selenurea 7 can be prepared. In the reaction of 12 with elemental sulfur and selenium the amidines 14 and 15, respectively, are formed. By treatment of 14 and 15 with alpha-halogenated carbonyl compounds and triethylamine the 1,3-thiazoles 18 and 1,3-selenazoles 19 can be prepared. The synthesis of the propynoic acid orthoamide 26b is described. 26b reacts with the guanidinium salt 24b to give the bis-orthoamide of butynedioic acid 20b. Other orthoamides of butynedioic acid 20b-20e can be synthesized from the orthoamide 20a by transamination. The thiolation of the orthoamides affords the bis-amidinium-dithiolates 21a-c, which can be alkylated to give the bis-amidinium salts 27. By treatment with alpha-halogene carbonyl compounds and triethylamine the dithiolates 21a-e are cyclized to give thieno [3,2b] thiophenes 28a-n. The quadrupoles 21 undergo cycloadditions with dimethyl-butynedioate which afford the bis(3H-thiophene-2 ylidenes) 29a-c. Treatment of 29a with methyl tosylate gives rise to the dithiophene 30a. The dithiophene 30b can be obtained by heating 21b with dimethylbutynedionate.

  DOI：

  10.1002/prac.19963380180