1-(2-Propyl-[1,3]dithiolan-2-yl)-ethanone | 136062-27-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 1-(2-Propyl-[1,3]dithiolan-2-yl)-ethanone
• 英文别名: 1-(2-propyl-1,3-dithiolan-2-yl)ethanone
• CAS: 136062-27-6
• 化学式: C₈H₁₄OS₂
• 分子量: 190.331
• InChiKey: WTNOCWFIPXGMHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-Propyl-[1,3]dithiolan-2-yl)-ethanone 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 三乙胺 作用下， 反应 72.0h， 生成 tert-Butyl-dimethyl-[1-((1R,2R)-1-oxo-2-propyl-1λ⁴-[1,3]dithiolan-2-yl)-vinyloxy]-silane
  参考文献：
  名称：

  Enhanced diastereo and enantioselectivity in the formation of acyldithiolane sulphoxides by the asymmetric oxidation of their enolsilyl ethers

  摘要：

  The sulphoxidation of the enol ethers of some acyldithiolanes using the Sharpless epoxidation reagents followed by fluorolysis results in better overall stereoselectivity than direct oxidation of the acyldithiolane thus providing a highly stereoselective route to acyldithiolane sulphoxides. Fluorolysis under acid conditions of non terminal enol ethers results in complete racemisation of the product. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01101-5
• 作为产物：
  描述：

  2,3-己二酮 、 1,2-乙二硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(2-Propyl-[1,3]dithiolan-2-yl)-ethanone 、 1-(2-Methyl-[1,3]dithiolan-2-yl)-butan-1-one
  参考文献：
  名称：

  Synthesis of 2,3-Dihydro-1,4-dithiins and 2-Alkylidene-1,4-dithianes by 1,2-Sulfur Migration in 2-(1-Hydroxyalkyl)-1,3-dithiolanes

  摘要：

  2,3-二氢-1,4-二硫烯和异构的2-烷基烯-1,4-二硫烷是通过在吡啶中用对甲苯磺酰氯对2-(1-羟基烷基)-1,3-二硫烷进行动力学控制的环扩展，从1,2-二酮和烷基丙酮酸酯合成的。此外，使用对甲苯磺酸在回流苯中，可以专门形成热力学产物2,3-二氢-1,4-二硫烯。2-烷基烯-1,4-二硫烷可轻易异构化为相应的2,3-二氢-1,4-二硫烯。同样，2,3-二甲基-6,7-二氢-5H-1,4-二硫哌啶和(+)-2-亚甲基-3-甲基-1,4-二硫烷是由2-[(S)-1-羟基乙基]-2-甲基-1,3-二硫烷得到的。

  DOI：

  10.1055/s-1991-26520

文献信息

• Synthesis of 2-Alkylidene-3,3-dialkyl-1,4-dithianes and Their Oxathiane Analogues by 1,2-Sulphur Migration
  作者：Christopher D. Maycock、M. Teresa Barros、Lúcia S. Santos

  DOI：10.3987/com-97-7898

  日期：——
• Synthesis of 2,3-Dihydro-1,4-dithiins and 2-Alkylidene-1,4-dithianes by 1,2-Sulfur Migration in 2-(1-Hydroxyalkyl)-1,3-dithiolanes
  作者：Carlos A. M. Afonso、M. Teresa Barros、Licio S. Godinho、Christopher D. Maycock

  DOI：10.1055/s-1991-26520

  日期：——

  2,3-Dihydro-1,4-dithiins and the isomeric 2-alkylidene-1,4-dithianes were synthesized from 1,2-diketones and alkyl pyruvates by kinetically controlled ring expansion of 2-(1-hydroxyalkyl)-1,3-dithiolanes with p-toluenesulfonyl chloride in pyridine. In addition, 2,3-dihydro-1,4-dithiins, the thermodynamic products, were formed exclusively by using p-toluenesulfonic acid in refluxing benzene. The 2-alkylidene-1,4-dithianes were readily isomerised to the corresponding 2,3-dihydro-1,4-dithiins. Similarly, 2,3-dimethyl-6, 7-dihydro-5H-1,4-dithiepine and (+)-2-methylene-3-methyl-1,4-dithiepane were obtained from 2-[(S)-1-hydroxyethyl]-2-methyl-1,3-dithiane.

  2,3-二氢-1,4-二硫烯和异构的2-烷基烯-1,4-二硫烷是通过在吡啶中用对甲苯磺酰氯对2-(1-羟基烷基)-1,3-二硫烷进行动力学控制的环扩展，从1,2-二酮和烷基丙酮酸酯合成的。此外，使用对甲苯磺酸在回流苯中，可以专门形成热力学产物2,3-二氢-1,4-二硫烯。2-烷基烯-1,4-二硫烷可轻易异构化为相应的2,3-二氢-1,4-二硫烯。同样，2,3-二甲基-6,7-二氢-5H-1,4-二硫哌啶和(+)-2-亚甲基-3-甲基-1,4-二硫烷是由2-[(S)-1-羟基乙基]-2-甲基-1,3-二硫烷得到的。
• Enhanced diastereo and enantioselectivity in the formation of acyldithiolane sulphoxides by the asymmetric oxidation of their enolsilyl ethers
  作者：M.Teresa Barros、Alcino J. Leitão、Christopher D. Maycock

  DOI：10.1016/s0040-4039(97)01101-5

  日期：1997.7

  The sulphoxidation of the enol ethers of some acyldithiolanes using the Sharpless epoxidation reagents followed by fluorolysis results in better overall stereoselectivity than direct oxidation of the acyldithiolane thus providing a highly stereoselective route to acyldithiolane sulphoxides. Fluorolysis under acid conditions of non terminal enol ethers results in complete racemisation of the product. (C) 1997 Published by Elsevier Science Ltd.