S-(Methylthio)methyl methanesulfonothioate

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: S-(Methylthio)methyl methanesulfonothioate
• 英文别名: 2,3,5-trithiahexane 2,2-dioxide；S-((methylthio)methyl) methanesulfonothioate；methylsulfanyl(methylsulfonylsulfanyl)methane
• 化学式: C₃H₈O₂S₃
• 分子量: 172.293
• InChiKey: SYAVJILWAIKGCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,4-三硫杂戊环 、 S-(Methylthio)methyl methanesulfonothioate 在 甲基锂 作用下， 以63%的产率得到2,4,5,7,9-pentathiadecane
  参考文献：
  名称：

  Simple Total Syntheses of Biologically Active Pentathiadecane Natural Products, 2,4,5,7,9-Pentathiadecane 2,2,9,9-Tetraoxide (Dysoxysulfone), from Dysoxylum richii, and 2,3,5,7,9-Pentathiadecane 9,9-Dioxide, the Misidentified Lenthionine Precursor SE-3 from Shiitake Mushroom (Lentinus edodes)

  摘要：

  Brief total syntheses are reported for 2,4,5,7,9-pentathiadecane 2,2,9,9-tetraoxide (dysoxysulfone, 1), from the Fijian tree Dysoxylum richii, 2,3,5,7,9-pentathiadecane 9,9-dioxide (8), from shiitake mushroom (Lentinus edodes),and 2,4,5,7-tetrathiaoctane 2,2-dioxide (2a) from Tulbaghia violacea, starting from 1,2,4-trithiolane (4) for 1, 1,2,4,6-tetrathiepane (5) for 8, and 2,4,5,7-tetrathiaoctane (9) for 2a and employing regiospecific oxidation of intermediate penta- or tetrasulfides using KMnO4 along with Zn(OAc)(2) or FeCl3 to prevent product degradation by the base produced during oxidation.

  DOI：

  10.1021/jo00088a001
• 作为产物：
  描述：

  氯甲基甲硫醚 、 硫甲磺酸钠 以 乙腈 为溶剂， 反应 5.5h， 以59%的产率得到S-(Methylthio)methyl methanesulfonothioate
  参考文献：
  名称：

  Simple Total Syntheses of Biologically Active Pentathiadecane Natural Products, 2,4,5,7,9-Pentathiadecane 2,2,9,9-Tetraoxide (Dysoxysulfone), from Dysoxylum richii, and 2,3,5,7,9-Pentathiadecane 9,9-Dioxide, the Misidentified Lenthionine Precursor SE-3 from Shiitake Mushroom (Lentinus edodes)

  摘要：

  Brief total syntheses are reported for 2,4,5,7,9-pentathiadecane 2,2,9,9-tetraoxide (dysoxysulfone, 1), from the Fijian tree Dysoxylum richii, 2,3,5,7,9-pentathiadecane 9,9-dioxide (8), from shiitake mushroom (Lentinus edodes),and 2,4,5,7-tetrathiaoctane 2,2-dioxide (2a) from Tulbaghia violacea, starting from 1,2,4-trithiolane (4) for 1, 1,2,4,6-tetrathiepane (5) for 8, and 2,4,5,7-tetrathiaoctane (9) for 2a and employing regiospecific oxidation of intermediate penta- or tetrasulfides using KMnO4 along with Zn(OAc)(2) or FeCl3 to prevent product degradation by the base produced during oxidation.

  DOI：

  10.1021/jo00088a001

文献信息

• Simple Total Syntheses of Biologically Active Pentathiadecane Natural Products, 2,4,5,7,9-Pentathiadecane 2,2,9,9-Tetraoxide (Dysoxysulfone), from Dysoxylum richii, and 2,3,5,7,9-Pentathiadecane 9,9-Dioxide, the Misidentified Lenthionine Precursor SE-3 from Shiitake Mushroom (Lentinus edodes)
  作者：Eric Block、Russell DeOrazio、Mohan Thiruvazhi

  DOI：10.1021/jo00088a001

  日期：1994.5

  Brief total syntheses are reported for 2,4,5,7,9-pentathiadecane 2,2,9,9-tetraoxide (dysoxysulfone, 1), from the Fijian tree Dysoxylum richii, 2,3,5,7,9-pentathiadecane 9,9-dioxide (8), from shiitake mushroom (Lentinus edodes),and 2,4,5,7-tetrathiaoctane 2,2-dioxide (2a) from Tulbaghia violacea, starting from 1,2,4-trithiolane (4) for 1, 1,2,4,6-tetrathiepane (5) for 8, and 2,4,5,7-tetrathiaoctane (9) for 2a and employing regiospecific oxidation of intermediate penta- or tetrasulfides using KMnO4 along with Zn(OAc)(2) or FeCl3 to prevent product degradation by the base produced during oxidation.