1,1,1,4,4,4-Hexakis(dimethylamino)-but-2-in | 130412-10-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,1,1,4,4,4-Hexakis(dimethylamino)-but-2-in
• 英文别名: 1-N,1-N,1-N',1-N',1-N",1-N",4-N,4-N,4-N',4-N',4-N",4-N"-dodecamethylbut-2-yne-1,1,1,4,4,4-hexamine
• CAS: 130412-10-1
• 化学式: C₁₆H₃₆N₆
• 分子量: 312.502
• InChiKey: MPKUPPGDELEGDB-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  110-111 °C(Press: 0.005 Torr)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1,1,4,4,4-Hexakis(dimethylamino)-but-2-in 在 sulfur 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.0h， 生成 (E)-3,3,3',3'-Tetrakis-dimethylamino-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：

  3,3,3-Tris(dimethylamino)-1-trimethylsilyl-prop-1-in 生成 1,1,1,4,4,4-Hexakis(dimethylamino)-but-2-in
  参考文献：
  名称：

  Kantlehner, Willi; Stieglitz, Ruediger; Hauber, Michael, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 3, p. 256 - 268

  摘要：

  DOI：

文献信息

• Orthoamide und Iminiumsalze, LXXXII [1]. Die Spaltung von Alkincarbonsäure-orthoamiden mit Trimethylsilylazid / Orthoamides and Iminium Salts LXXXII [1]. The Cleavage of Orthoamides of Alkynecarboxylic Acids by Trimethylsilyl Azide
  作者：Willi Kantlehner、Kai Edelmann、Wolfgang Frey

  DOI：10.5560/znb.2012-0124

  日期：2012.9.1

  The cleavage of orthoamides of alkynecarboxylic acids 5 with trimethylsilyl azide affords 4-[bis(dimethylamino)methylene]-4H-1,2,3-triazoles 9. By treatment of the bis-orthoamide of acetylenedicarboxylic acid 1 with trimethylsilyl azide and benzoyl azide, respectively, the 5- [bis(dimethylamino)methylene]-5H-1,2,3-triazole carboxamidinium salt 12a is accessible. Iminium salts 10 and 14 can be prepared by methylation of the triazoles 9 and 12a in 2-position of the triazole ring. The crystal structure of 5H-1,2,3-triazole-4-carboxamidinium tetraphenylborate 12b is reported

  用三甲基硅叠氮化物裂解炔羧酸 5 的原酰胺，可得到 4-[双（二甲基氨基）亚甲基]-4H-1,2,3-三唑 9。分别用三甲基硅叠氮化物和苯甲酰叠氮化物处理乙炔二甲酸 1 的双正酰胺，可得到 5-[双（二甲基氨基）亚甲基]-5H-1,2,3-三唑羧酰胺鎓盐 12a。通过将三唑 9 和 12a 在三唑环的 2 位进行甲基化，可以制备出氨盐 10 和 14。据报道，5H-1,2,3-三唑-4-羧酰胺鎓四苯基硼酸盐 12b 的晶体结构为
• KANTLEHNER, WILLI;SPEH, PETER;LEHMANN, HANSJORG;BRAUNER, HANS-JURGEN;HAUG+, CHEM.-ZTG., 114,(1990) N, C. 176-178
  作者：KANTLEHNER, WILLI、SPEH, PETER、LEHMANN, HANSJORG、BRAUNER, HANS-JURGEN、HAUG+

  DOI：——

  日期：——
• KANTLEHNER, WILLI;LEHMANN, HANSJORG;STAHL, THOMAS;KAIM, WOLFGANG, CHEM. -ZIG., 115,(1991) N, C. 183-186
  作者：KANTLEHNER, WILLI、LEHMANN, HANSJORG、STAHL, THOMAS、KAIM, WOLFGANG

  DOI：——

  日期：——