(S)-5-(2-methyl-1-phenylpropyl)-3H-1,2,4-dithiazol-3-one | 1337959-58-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-5-(2-methyl-1-phenylpropyl)-3H-1,2,4-dithiazol-3-one
• CAS: 1337959-58-6
• 化学式: C₁₂H₁₃NOS₂
• 分子量: 251.373
• InChiKey: HLNXGNIQOZEVPJ-JTQLQIEISA-N

物化性质

• 沸点：
  366.6±35.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (2R)-3-methyl-2-phenylbutanoyl chloride 在 劳森试剂 、 吡啶 、 ammonium hydroxide 、 水 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 24.03h， 生成 (S)-5-(2-methyl-1-phenylpropyl)-3H-1,2,4-dithiazol-3-one
  参考文献：
  名称：

  Synthesis of chiral disulfides: potential reagents for enantioselective sulfurization

  摘要：

  Synthesis of chiral phosphorothioates for use as antisense oligonucleotides might benefit from the use of chiral disulfides. This paper reports the synthesis of chiral analogs of phenylacetyl disulfide and of 5-methyl-3H-1,2,4-dithiazol-3-one from the same set of 2-arylalkanoic acids. The X-ray crystal structures of the disulfides derived from (R) and [S]-2-phenylpropanoic acid establish the stereochemistry and the helicity of these materials, and density functional theory calculations suggest that the high specific rotations can be due to preferred retention of this helicity in solution. Chiral HPLC showed that the final products were formed with enantiomeric purities from 86.1% to99.9%. [image omitted].

  DOI：

  10.1080/17415993.2011.580346
• 作为试剂：
  描述：

  [(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl] [(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl trimethylsilyl phosphite 、 三乙基碳酸氢铵缓冲液 在 (S)-5-(2-methyl-1-phenylpropyl)-3H-1,2,4-dithiazol-3-one 、 水 作用下， 以 乙腈 、 甲苯 为溶剂， 反应 20.0h， 生成 、
  参考文献：
  名称：

  Sulfurization of Dinucleoside Phosphite Triesters with Chiral Disulfides

  摘要：

  Sixteen chiral analogues of phenylacetyl disulfide (PADS) and 5-methyl-3H-1,2,4-dithiazol-3-one (MEDITH) were used to sulfurize five dithymidine phosphite triesters, each incorporating a beta-cyanoethoxy or siloxy group. Each mixture of S-p:R-p, phosphite triester diastereomers was combined with approximately one fourth of an equivalent of each of the sulfurizing reagents, and the R-ps:S-ps diastereomer ratios of the resulting phosphite sulfides or phosphorothioates were determined by reverse-phase HPLC. Diastereoselectivities and corresponding diastereomeric excess (de) values were calculated by correcting for the starting triester diastereomer ratios. The highest de values for R-ps and S-ps phosphorothioates were 14.7% and 7.9%, respectively, both using MEDITH analogues.

  DOI：

  10.1080/15257770.2011.597366