3-Amino-5-methyl-N,N-dimethyl-2,4-hexadienthioamid | 140868-76-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 英文名称: 3-Amino-5-methyl-N,N-dimethyl-2,4-hexadienthioamid
• 英文别名: 3-amino-N,N,5-trimethylhexa-2,4-dienethioamide
• CAS: 140868-76-4
• 化学式: C₉H₁₆N₂S
• 分子量: 184.305
• InChiKey: LSPOHGASYNELNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Amino-5-methyl-N,N-dimethyl-2,4-hexadienthioamid 在 氢氧化钾 、 双氧水 作用下， 以 乙醇 为溶剂， 以1.6 g的产率得到5-dimethylamino-3-(2-methyl-1-propenyl)-1,2-thiazole
  参考文献：
  名称：

  1,2-Thiazole durch Ringtransformation von 2H-Thiopyran-2-thionen

  摘要：

  Aminolyses of 4-dialkylamino-2-methylthiothiopyranes halides with ammonia leads to 4-amino-2-dialkylaminothiopyranylium halides. On treatment with alkali these products are hydrolyzed to N,N-dialkyl-3-amino-2,4-hexadienthioamides, which react with peroxide under oxidative cyclization to 5-dialkylamino-1,2-thiazoles. In order to determine the structures of the unsaturated thioamides and isothiazoles C-13-NMR-spectroscopic analysis and a single crystal X-ray structure analysis of 5-dimethylamino-3-(2-methyl-1-propenyl)-1,2-thiazole (6a) at 100 K were carried out: C9H14N2S, M(r) = 182.28, monoclinic, P 2(1)/a, a = 11.622(2), b = 6.303(1), c = 13.678(2), beta = 104.49(3)-degrees, V = 970.1 (3)angstrom3, Z = 4, d(x) = 1.248 g/cm3, mu = 27.0 mm-1, R = 4.93%, R(w) = 4.84% (1672 observations, 157 parameters).

  DOI：

  10.1007/bf01045306
• 作为产物：
  描述：

  (2,2-dimethyl-6-methylsulfanyl-3H-thiopyran-4-ylidene)-dimethylazanium;iodide 在 sodium hydroxide 、 氨 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 24.0h， 生成 3-Amino-5-methyl-N,N-dimethyl-2,4-hexadienthioamid
  参考文献：
  名称：

  1,2-Thiazole durch Ringtransformation von 2H-Thiopyran-2-thionen

  摘要：

  Aminolyses of 4-dialkylamino-2-methylthiothiopyranes halides with ammonia leads to 4-amino-2-dialkylaminothiopyranylium halides. On treatment with alkali these products are hydrolyzed to N,N-dialkyl-3-amino-2,4-hexadienthioamides, which react with peroxide under oxidative cyclization to 5-dialkylamino-1,2-thiazoles. In order to determine the structures of the unsaturated thioamides and isothiazoles C-13-NMR-spectroscopic analysis and a single crystal X-ray structure analysis of 5-dimethylamino-3-(2-methyl-1-propenyl)-1,2-thiazole (6a) at 100 K were carried out: C9H14N2S, M(r) = 182.28, monoclinic, P 2(1)/a, a = 11.622(2), b = 6.303(1), c = 13.678(2), beta = 104.49(3)-degrees, V = 970.1 (3)angstrom3, Z = 4, d(x) = 1.248 g/cm3, mu = 27.0 mm-1, R = 4.93%, R(w) = 4.84% (1672 observations, 157 parameters).

  DOI：

  10.1007/bf01045306

文献信息

• Synthese von 5-Dialkylamino-1,2-oxazolen aus N,N-Dialkyl-?-amino-?,?,?,?-unges�ttigten Thioamiden
  作者：H. Auer、R. Weis、K. Schweiger、M. Schubert-Szilavecz

  DOI：10.1007/bf00811850

  日期：1994.5

  3-Amino-2,4-pentadienthioamides, which were obtained from 6-dialkylamino-2H-thiopyrane-4(3H)iminium halides by alkali hydrolysis, react with hydroxylamine hydrochloride in a [C-C-C]+[N-O]-addition to give selectively 5-amino-3-alkenyl-1,2-oxazoles. These oxazoles have been identified by C-13 and H-1 NMR spectroscopic analysis. The configuration of these compounds was established on the basis of the coupling constants and 2D-NOESY-experiments. The position of the substituents has been determined by analysis of the fragmentation pattern.