ethyl piperidine-1-carbodithioate | 16022-57-4

• 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: ethyl piperidine-1-carbodithioate
• 英文别名: piperidine-1-carbodithioic acid ethyl ester；Piperidin-1-dithiocarbonsaeure-aethylester
• CAS: 16022-57-4
• 化学式: C₈H₁₅NS₂
• 分子量: 189.346
• InChiKey: GODAWSWFAMASSD-UHFFFAOYSA-N

物化性质

• 沸点：
  155-159 °C(Press: 3 Torr)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl piperidine-1-carbodithioate 在 乙醇 、 一水合肼 作用下， 生成 硫代卡巴肼
  参考文献：
  名称：

  Notes - Hydrazinolysis of 1-(Alkyldithioate)-piperidine

  摘要：

  DOI：

  10.1021/jo01352a610
• 作为产物：
  描述：

  碘乙烷 、 sodium piperidinedithiocarbamate 在 乙醇 作用下， 生成 ethyl piperidine-1-carbodithioate
  参考文献：
  名称：

  Notes - Hydrazinolysis of 1-(Alkyldithioate)-piperidine

  摘要：

  DOI：

  10.1021/jo01352a610

文献信息

• Straightforward and Highly Efficient Catalyst-Free One-Pot Synthesis of Dithiocarbamates under Solvent-Free Conditions
  作者：Najmedin Azizi、Fezzeh Aryanasab、Mohammad R. Saidi

  DOI：10.1021/ol0620141

  日期：2006.11.9

  [Structure: see text] A highly efficient and simple synthesis of dithiocarbamates is possible based on the one-pot reaction of amines, CS2, and alkyl halides without using a catalyst under solvent-free conditions. The mild reaction conditions, high yields, and broad scope of the reaction illustrate the good synthetic utility of this method. The reaction is a highly atom-economic process for production

  [结构：见正文]基于胺，CS2和烷基卤化物的一锅反应，在无溶剂条件下无需使用催化剂，即可高效且简单地合成二硫代氨基甲酸酯。温和的反应条件，高收率和广泛的反应范围说明了该方法的良好合成实用性。该反应是生产S-烷基硫代氨基甲酸酯的高度原子经济的方法，可成功地大量用于制药或农业化学工业。
• Efficient, straightforward, catalyst-free synthesis of medicinally important S-alkyl/benzyl dithiocarbamates under green conditions
  作者：Ali Asadipour、Zeynab Shams、Khalil Eskandari、Mohammad-Hassan Moshafi、Ehsan Faghih-Mirzaei、Yaghoub Pourshojaei

  DOI：10.1007/s11164-017-3167-1

  日期：2018.2

  among aliphatic amines, those which reacted with benzyl halides showed better yields than those that reacted with alkyl halides. Use of environmentally benign solvents is one of the advantages of this procedure. Also, obtaining products in good yield via catalyst-free reaction using a facile, inexpensive, and practical approach can be considered other advantages of this procedure. Target products

  描述了通过有效的一锅无催化剂反应，绿色合成的一些新型的二硫代氨基甲酸酯衍生物，它们被脂族和芳族基团取代，这可能是有趣的，对医学有重要意义的有机化合物。在该反应中，二硫代氨基甲酸酯衍生物是通过在一锅和乙醇水溶液中的伯胺或仲胺，二硫化碳以及烷基或苄基卤化物之间的缩合反应获得的。在脂族和芳族胺中，结果通常显示脂族胺与烷基或苄基卤化物的反应以最高收率得到所需产物。同样，在脂族胺中，与苄基卤反应的那些比与烷基卤反应的那些显示出更好的产率。使用对环境无害的溶剂是该程序的优势之一。也，通过简便，廉价且实用的方法通过无催化剂反应获得高收率的产物，可以认为是该方法的其他优点。目标产品是非常重要的化合物，因为它们的类似物已用于制药，化学和橡胶工业。
• TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF
  申请人：Gin David

  公开号：US20130011421A1

  公开（公告）日：2013-01-10

  The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.

  本发明涉及从三萜苷甙皂苷中衍生的佐剂，其合成，中间体以及用途。 QS-7是一种有效的免疫佐剂，比QS-21毒性显著降低，QS-21是目前抗癌和抗病毒疫苗中备受青睐的佐剂。繁琐的分离和纯化方案阻碍了QS-7的临床开发。提供了一种新的半合成方法，其中使用水解的原皂苷混合物来合成QS-7，QS-21和相关类似物，极大地便于获得QS-7和QS-21类似物进行临床前和临床评估。
• Design and synthesis of new family of ionic liquids based on 2-iminium-1,3-dithiolanes: A combined theoretical and experimental effort
  作者：Azim Ziyaei Halimehjani、Mehdi Shakourian-Fard、Marziye Vahdati Farvardin、Mozhgan Raeesi、Mohammed Mahmoodi Hashemi、Hadi Behzadi

  DOI：10.1016/j.molstruc.2013.10.017

  日期：2014.1

  An efficient method for synthesis of 2-iminium-1,3-dithiolane as a new family of ionic liquids with reaction of dithiocarbamates with methyl triflouromethanesulfonate was described. Theoretical study on the synthesized ionic liquids was also performed by quantum chemistry calculation. Geometry optimization on the ion pairs was carried out with the B3LYP/6-311++G(d,p) level of theory. The interaction energies were calculated, and corrected by the basis set superposition error (BSSE) calculated by the counterpoise method. The results of natural bond orbital (NBO) and quantum theory of atoms in molecules (QTAIM) analyses indicate that the interactions occur via hydrogen bonding between oxygen atom lone pairs (lp(O)) of triflouromethanesulfonate anion and antibonding orbitals of sigma*C-H of 2-iminium-1,3-dithiolane cations. Also, the results of QTAIM analysis show that the hydrogen bonds are closed shell (electrostatic) in the nature. Finally, the H-1 and C-13 calculated chemical shifts at the B3LYP/6-311++G** level were in agreement with experimental chemical shifts for synthesized ionic liquids. (C) 2013 Elsevier B.V. All rights reserved.
• A New Route to Dithiocarbamates from Tertiary N-Methyl and N-Benzylamines
  作者：M. D. Pujol、G. Guillaumet

  DOI：10.1080/00397919208019304

  日期：1992.5

  The sequential treatment of various tertiary N-methyl and N-benzylamines with carbon disulfide, and then with an alkyl halide in tetrahydrofuran gave the corresponding dithiocarbamates in good to excellent yields.