(1S,2S)-2-methyl-1,3-dithian 1-oxide | 87480-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: (1S,2S)-2-methyl-1,3-dithian 1-oxide
• 英文别名: anti-2-methyl-1,3-dithiane 1S-oxide；(1S,2S)-trans-2-methyl-1,3-dithiane-1-oxide；(1S,2S)-2-methyl-1,3-dithiane 1-oxide
• CAS: 87480-75-9
• 化学式: C₅H₁₀OS₂
• 分子量: 150.266
• InChiKey: CZILJPDWGUDUME-XNCJUZBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基-1,3-二噻烷 生成 (1S,2S)-2-methyl-1,3-dithian 1-oxide
  参考文献：
  名称：

  AURET, B. J.;BOYD, D. R.;CASSIDY, E. S.;TURLEY, F.;DRAKE, A. F.;MASON, S.+, J. CHEM. SOC. CHEM. COMMUN., 1983, N 6, 282-283

  摘要：

  DOI：

文献信息

• Enantioselective preparation of 2-substituted- 1,3-dithiane 1-oxides using modified sharpless sulphoxidation procedures
  作者：Philip C. Bulman Page、Robin D. Wilkes、Emest S. Namwindwa、Michael J. Witty

  DOI：10.1016/0040-4020(95)01029-7

  日期：1996.2

  carried out using modified Sharpless conditions to furnish the corresponding sulphoxides in optically enriched form. Deacylation of 2-acyl-1,3-dithiane 1-oxide derivatives allows the preparation of 2-alkyl-1,3-dithiane 1-oxides and the parent 1,3-dithiane 1-oxide itself in high enantiomeric excesses.

  已经使用改良的Sharpless条件进行了范围广泛的2-取代的1,3-二硫杂环丁烷的对映选择性磺氧化，以提供光学富集形式的相应亚砜。2-酰基-1,3-二硫杂环丁烷1-氧化物衍生物的脱酰作用可以制备2-烷基-1,3-二硫杂环丁烷1-氧化物和母体1,3-二硫杂环丁烷1-氧化物本身以高对映体过量的方式制备。
• Stereoselectivity of prochiral thioalkyl groups in the enzymatic oxidation of thioacetals by fungi
  作者：Barbara J. Auret、Derek R. Boyd、E. Sally Cassidy、Fiona Turley、Alex F. Drake、Stephen F. Mason

  DOI：10.1039/c39830000282

  日期：——

  Enzymatic oxidation of 2-substituted 1,3-dithians in cultures of a Helminthosporium species shows a stereoperference for equatorial oxidation and for (1S)-monosulphoxide products.

  在蠕虫属菌种的培养物中2-取代的1,3-二硫杂环丁烷的酶促氧化显示赤道氧化和（1 S）-单亚砜产物的立体异构。
• Enantio and diastereoselectivity of cyclohexanone monooxygenase catalyzed oxidation of 1,3-dithioacetals
  作者：Stefano Colonna、Nicoletta Gaggero、Giacomo Carrea、Piero Pasta

  DOI：10.1016/0957-4166(96)00040-7

  日期：1996.2

  The asymmetric oxidation of 2-substituted dithianes, dithiolanes and oxathiolanes catalyzed by cyclohexanone monooxygenase (CMO) has been examined. The introduction of substituents at the C-2 causes a decrease of the e.e. with the exception of 2-benzoyl-1, 3-dithiane monosulfoxide (90% ea.). With 2-monosubstituted dithioacetals CMO yields preferentially or exclusively the trans diastereoisomer. The binding of the 1, 3-dithioacetals at the active site of the enzyme is not only controlled by the sterical hindrance of the substituents in position 2 but also by the configuration at C-2. The stereoselectivity of CMO has been compared with that reported for microsomal flavin and cytochrome P-450 monooxygenases.
• AURET, B. J.;BOYD, D. R.;CASSIDY, E. S.;TURLEY, F.;DRAKE, A. F.;MASON, S.+, J. CHEM. SOC. CHEM. COMMUN., 1983, N 6, 282-283
  作者：AURET, B. J.、BOYD, D. R.、CASSIDY, E. S.、TURLEY, F.、DRAKE, A. F.、MASON, S.+

  DOI：——

  日期：——