4-Acetylamino-5,5-dimethyl-1,2-dithiolan-3-one | 109795-69-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-Acetylamino-5,5-dimethyl-1,2-dithiolan-3-one
• 英文别名: 4-acetylamino-5,5-dimethyl-[1,2]dithiolan-3-one；4-Acetylamino-5,5-dimethyl-[1,2]dithiolan-3-on；N-(3,3-dimethyl-5-oxo-1,2-dithiolan-4-yl)acetamide；N-(3,3-dimethyl-5-oxodithiolan-4-yl)acetamide
• CAS: 109795-69-9
• 化学式: C₇H₁₁NO₂S₂
• 分子量: 205.302
• InChiKey: AJMJTRFJMQDJDE-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Acetylamino-5,5-dimethyl-1,2-dithiolan-3-one 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 生成 N-((1R,4S)-5,5-Dimethyl-1,3-dioxo-1λ⁴-[1,2]dithiolan-4-yl)-acetamide 、 N-((1S,4S)-5,5-Dimethyl-1,3-dioxo-1λ⁴-[1,2]dithiolan-4-yl)-acetamide
  参考文献：
  名称：

  Diastereoselective oxidation of substituted 1,2-dithiolan-3-ones

  摘要：

  Oxidation of 1,2-dithiolan-3-ones 1 with one equivalent of dimethyldioxirane in dichloromethane at -78 degrees C produces the corresponding 1,2-dithiolan-3-one 1-oxides 2 in high yield and with diastereoselectivities as high as 18:1. The major diastereomer formed is the trans isomer. An X-ray crystallographic structure study of the major diastereomer 2c obtained by oxidation of 1g is reported.

  DOI：

  10.1016/s0040-4039(00)76693-7
• 作为产物：
  描述：

  α-Acetylamino-β,β-dimethyl-β-propiothiolactone 在 硫化氢 、 三氯化铁 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 15.0h， 生成 4-Acetylamino-5,5-dimethyl-1,2-dithiolan-3-one
  参考文献：
  名称：

  Synthesis and biological activity of mercaptothiocarboxylic acids and their cyclic analogs

  摘要：

  DOI：

  10.1007/bf00765107

文献信息

• Synthesis and biological activity of mercaptothiocarboxylic acids and their cyclic analogs
  作者：N. I. Lisina、T. P. Vasil'eva、V. M. Bystrova、O. V. Kil'disheva、G. A. Chernov

  DOI：10.1007/bf00765107

  日期：1987.2
• Foeldi, Acta Chimica Academiae Scientiarum Hungaricae, 1953, vol. 3, p. 501,508
  作者：Foeldi

  DOI：——

  日期：——
• LISINA N. I.; VASILEVA T. P.; BYSTROVA V. M.; KILDISHEVA O. V.; CHERNOV G+, XIM.-FARMATS. ZH., 21,(1987) N 2, 177-181
  作者：LISINA N. I.、 VASILEVA T. P.、 BYSTROVA V. M.、 KILDISHEVA O. V.、 CHERNOV G+

  DOI：——

  日期：——
• Cyclic Acyl Disulfides and Acyl Selenylsulfides as the Precursors for Persulfides (RSSH), Selenylsulfides (RSeSH), and Hydrogen Sulfide (H₂S)
  作者：Jianming Kang、Aaron J. Ferrell、Wei Chen、Difei Wang、Ming Xian

  DOI：10.1021/acs.orglett.7b04005

  日期：2018.2.2

  The reactions of three model compounds (1-3) for cyclic acyl disulfides and cyclic acyl selenylsulfides are studied. These compounds were found to be effective precursors for persulfides (RSSH) and selenylsulfides (RSeSH) upon reacting with nucleophilic species. They could also act as H2S donors when interacting with cellular thiols. The most interesting discovery was the generation of RSeSH from compound 3 under mild conditions. Selenylsulfides (RSeSH) are expected to be important regulating molecules involved in Sec-related redox signaling. The method of producing RSeSH should allow researchers to better understand the chemical biology of RSeSH.
• Diastereoselective oxidation of substituted 1,2-dithiolan-3-ones
  作者：Richard S. Glass、Yunqi Liu

  DOI：10.1016/s0040-4039(00)76693-7

  日期：1994.6

  Oxidation of 1,2-dithiolan-3-ones 1 with one equivalent of dimethyldioxirane in dichloromethane at -78 degrees C produces the corresponding 1,2-dithiolan-3-one 1-oxides 2 in high yield and with diastereoselectivities as high as 18:1. The major diastereomer formed is the trans isomer. An X-ray crystallographic structure study of the major diastereomer 2c obtained by oxidation of 1g is reported.