1,3-二(硫氰酸基)丙烷 | 7314-74-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫氰酸盐
• 中文名称: 1,3-二(硫氰酸基)丙烷
• 英文名称: 1,3-bis(thiocyanato)propane
• 英文别名: 1,3-dithiocyanatopropane；1,3-Dithiocyanato-propan；Trimethylendithiocyanat；Thiocyanic acid, 1,3-propanediyl ester；3-thiocyanatopropyl thiocyanate
• CAS: 7314-74-1
• 化学式: C₅H₆N₂S₂
• 分子量: 158.248
• InChiKey: REUWYUITIHLJNM-UHFFFAOYSA-N

物化性质

• 沸点：
  129-130 °C(Press: 0.05 Torr)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-二(硫氰酸基)丙烷 在 水 、 氯 作用下， 生成 丙烷-1,3-二(磺酰氯)
  参考文献：
  名称：

  Asinger; Schmidt; Ebendener, Chemische Berichte, 1942, vol. 75, p. 40

  摘要：

  DOI：
• 作为产物：
  描述：

  在 盐酸 作用下， 生成 1,3-二(硫氰酸基)丙烷
  参考文献：
  名称：

  Ardrey,R.E.; Cort,L.A., Journal of the Chemical Society. Perkin transactions I, 1976, p. 121 - 124

  摘要：

  DOI：

文献信息

• Syntheses and solid state structures of cyclic diynes with two chalcogen centres ? a competition between weak interactions
  作者：J. Hilko Schulte、Daniel B. Werz、Frank Rominger、Rolf Gleiter

  DOI：10.1039/b303653g

  日期：——

  Structural investigations by means of X-ray diffraction reveal for most systems a chair-like conformation in the solid state. For 5S(2)2, 5S(2)3, 7S(2)5, 5Se(2)2 and 5Te(2)3 tubular structures were encountered. These structures can be traced back to weak XX or weak C-Hpi interactions.

  在本文中，我们报告了通式为mX2n的环状二炔的合成。字母m和n表示两个C三键CX单元之间的链长，其中X表示S，Se或Te。桥的长度在m = 4-8和n = 2-6之间变化。通过X射线衍射进行的结构研究表明，对于大多数系统而言，固态呈椅子状构象。对于5S（2）2、5S（2）3、7S（2）5、5Se（2）2和5Te（2）3，遇到管状结构。这些结构可以追溯到弱XX或弱C-Hpi相互作用。
• 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。
• Use of 3-[¹⁸F]fluoropropanesulfonyl chloride as a prosthetic agent for the radiolabelling of amines: Investigation of precursor molecules, labelling conditions and enzymatic stability of the corresponding sulfonamides
  作者：Reik Löser、Steffen Fischer、Achim Hiller、Martin Köckerling、Uta Funke、Aurélie Maisonial、Peter Brust、Jörg Steinbach

  DOI：10.3762/bjoc.9.115

  日期：——

  were accessible in satisfactory yields owing to systematic variation of the reaction conditions. With respect to the application of the (18)F-fluoropropansulfonyl group to the labelling of compounds relevant as imaging agents for positron emission tomography (PET), the stability of N-(4-fluorophenyl)-3-fluoropropanesulfonamide against degradation catalysed by carboxylesterase was investigated and compared

  3-[(18)F] 氟丙烷磺酰氯是一种最近提出的用于氟 18 标记的假体剂，是通过 3-[(18)F] 氟丙基硫氰酸酯作为中间体在两步放射合成中制备的。通过各种途径制备了两种基于苯磺酸盐的放射性标记前体。比较 3-硫氰基丙基诺磺酸酯和相应的甲苯磺酸酯对 [(18)F] 氟化物的反应性，证明前者是优越的，标记产率高达 85%。已确定将 3-[(18) F] 氟丙基硫氰酸酯可靠转化为具有自动化潜力的相应磺酰氯的条件。研究了 3-[(18) F] 氟丙烷磺酰氯与八种不同的脂肪族和芳香族胺的反应，并通过与非放射性对应物的比较色谱法确认了所得 (18) F 标记的磺酰胺的身份。即使对于弱亲核胺，如 4-硝基苯胺，由于反应条件的系统变化，所需的放射性标记磺胺也能以令人满意的产率获得。关于 (18)F-氟丙磺酰基在标记与正电子发射断层扫描 (PET) 成像剂相关的化合物中的应用，N-(4-氟苯基)-3-
• DIRECT SYNTHESIS OF PROTECTED THIOLS BY TRIBUTYLSTANNYL GROUP
  作者：Yoshio Ueno、Mamoru Nozomi、Makoto Okawara

  DOI：10.1246/cl.1982.1199

  日期：1982.8.5

  Organic thiocyanates react with tributyltin hydride under homolytic conditions to give thiostannanes (Bu3Sn–SR), which are air-stable and high boiling protected forms of the parent thiols.

  有机硫氰酸盐在均裂条件下与氢化三丁基锡反应生成硫锡烷 (Bu3Sn-SR)，这是母体硫醇的空气稳定和高沸点保护形式。
• Syntheses and Structural Properties of Cyclic Tetrathiadiynes
  作者：Christoph Benisch、Sabine Bethke、Rolf Gleiter、Thomas Oeser、Hans Pritzkow、Frank Rominger

  DOI：10.1002/1099-0690(200007)2000:13<2479::aid-ejoc2479>3.0.co;2-9

  日期：2000.7

  The four-component cyclization of dilithium acetylide with dithiocyanatoalkanes yielded the hitherto unknown tetrathiacyclodiynes 34, 38, 41, and 43 in moderate yields. The use of the trimethylsilyl protecting group allowed a more efficient and flexible stepwise approach with good yields. The resulting tetrathiacyclodiynes 25−44 were investigated by X-ray analysis. For ring systems with a twist-chair

  与dithiocyanatoalkanes二锂乙炔化物的四种成分的环化，得到迄今未知的tetrathiacyclodiynes 34，38，41，和43在中等产率。三甲基甲硅烷基保护基的使用允许具有良好收率的更有效和灵活的逐步方法。将所得tetrathiacyclodiynes 25 - 44通过X射线分析调查。用于与拧椅式构象的环系统中的CH的扭转角2 -Sσ-键的CH的2 -S-C≡C-S-CH 2部分采用75°和110之间的值°。这些值是由电子效应引起的，如HF / 6-31G *计算所示。