2-thiocyanato-butyric acid methyl ester | 68521-55-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-thiocyanato-butyric acid methyl ester
• 英文别名: 2-Thiocyanato-buttersaeure-methylester；α-Rhodan-buttersaeure-methylester；Methyl 2-thiocyanatobutanoate
• CAS: 68521-55-1
• 化学式: C₆H₉NO₂S
• 分子量: 159.209
• InChiKey: ILIUTAHXTGCGNP-UHFFFAOYSA-N

物化性质

• 沸点：
  114-117 °C(Press: 16 Torr)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-thiocyanato-butyric acid methyl ester 在 盐酸 作用下， 生成 2,4-Dioxo-5-ethyl-thiazolidin
  参考文献：
  名称：

  Wheeler; Barnes, American Chemical Journal, 1900, vol. 24, p. 80

  摘要：

  DOI：
• 作为产物：
  描述：

  potassium thioacyanate 、 alkaline earth salt of/the/ methylsulfuric acid 生成 2-thiocyanato-butyric acid methyl ester
  参考文献：
  名称：

  Wheeler; Barnes; North, American Chemical Journal, 1900, vol. 24, p. 79,80

  摘要：

  DOI：

文献信息

• SYNTHESIS OF 2,4-THIAZOLIDINEDIONE-2-AZINES AND 2,4-THIAZOLIDINEDIONE-2-DIMETHYLHYDRAZONES FROM THIOCYANOESTERS AND HYDRAZINES
  作者：Paul E. Gagnon、Jean-L. Boivin、Gordon M. Brown

  DOI：10.1139/v59-231

  日期：1959.9.1

  Thiocyanoesters were prepared from 2-bromoesters and potassium thiocyanate, and a series of substituted thiazolidinedione-2-azines was obtained from these thiocyanoesters using hydrazine hydrate. The structure of the thiazolidinedione-2-azines was determined by hydrolysis using hydrochloric acid in ethanol. The reaction of thiocyanoesters with dimethylhydrazine, generally speaking, was analogous to their reaction with hydrazine, but there were many differences. Only 1 mole of alcohol was eliminated rather than 2, and there was no apparent reaction for the ethyl 2-thiocyanononanoate and the methyl phenylthiocyanoacetate. Furthermore, the reaction of methyl 2-thiocyanoisobutyrate with dimethylhydrazine did not give a 2,4-thiazolidinedione-2-dimethylhydrazone but rather an addition product, N-dimethylamino-S-(1-methyl-1-carbomethoxy) ethylisothiourea. To illustrate the reactivity of the thiocyano group, benzyl thiocyanate was treated with hydrazine and the product was found to be dibenzyldisulphide, and ammonia was evolved. Similarly, trimethylene dithiocyanate gave the dimer of trimethylene disulphide. Finally, benzyl thiocyanate formed an addition product with dimethylhydrazine which was N-dimethylamino-S-benzylthiourea.

  硫氰酸酯由2-溴酯和硫氰酸钾制备，并通过硫氰酸酯与水合肼反应获得一系列取代的噻唑烷二酮-2-嗪。噻唑烷二酮-2-嗪的结构通过在乙醇中使用盐酸水解确定。硫氰酸酯与二甲基肼的反应，一般来说，类似于它们与肼的反应，但存在许多差异。只有1摩尔的醇被消除而不是2摩尔，并且乙基2-硫氰基壬酸酯和甲基苯基硫氰基乙酸酯没有明显的反应。此外，甲基2-硫氰基异丁酸酯与二甲基肼的反应没有生成2,4-噻唑烷二酮-2-二甲基脒，而是生成了加成产物，N-二甲氨基-S-(1-甲基-1-羰基甲氧基)乙基异硫脲。为了说明硫氰酸基团的反应性，苯基硫氰酸酯与肼反应，产物被发现是二苯基二硫化物，并释放出氨。同样，三甲基二硫氰酸酯生成了三甲基二硫化物的二聚体。最后，苯基硫氰酸酯与二甲基肼形成了一个加成产物，即N-二甲氨基-S-苯基硫脲。