[5-Methylsulfanyl-6-(sulfanylmethyl)-11-azatricyclo[5.3.1.04,11]undeca-1,3,5,7,9-pentaen-2-yl]methanethiol | 130540-57-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: [5-Methylsulfanyl-6-(sulfanylmethyl)-11-azatricyclo[5.3.1.04,11]undeca-1,3,5,7,9-pentaen-2-yl]methanethiol
• CAS: 130540-57-7
• 化学式: C₁₃H₁₃NS₃
• 分子量: 279.451
• InChiKey: TXOCOIOZDJMTCO-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C
• 密度：
  1.41±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  31.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-双(溴甲基)吡啶 、 [5-Methylsulfanyl-6-(sulfanylmethyl)-11-azatricyclo[5.3.1.04,11]undeca-1,3,5,7,9-pentaen-2-yl]methanethiol 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以7%的产率得到2,12-dithia-5-methylthio[3](2,6)pyridino[3](1,4)cycl[3.2.2]azinophane
  参考文献：
  名称：

  Synthesis of 2,12-Dithia[3](2,6)pyridino[3](1,4)cycl[3.2.2]azinophane and It's Barrier to Methylene Twist

  摘要：

  A synthesis of the title compound (11) is completed starting from indolizine (3). Key intermediate, bis(mercaptomethyl)cycl[3.2.2]azine (9) has been synthesized by reduction of bis(acetylthiomethyl)cycl[3.2.2]azine (8) with LiAlH4. 2, 12-Dithia[3] (2,6)pyridino[3](1,4)cycl[3.2.2]azinophanes (11a,b) have been synthesized by the reaction of 9 with 2,6-bis(bromomethyl)pyridine (10) in the presence of Cs2CO3 by the high dilution method. In the H-1-nmr spectrum of 11a,b, these exist in the syn conformation in their H-1-nmr spectra With regard to 2, 12-dithia[3](2,6)pyridino[3](1,4)cycl[3.2.2]azinophane (11a), the coalescence temperature for the methylene twist yields an activation barrier, Delta G(double dagger), of 79.5 ki mol(-1) for variable temperature (VT) nmr method.

  DOI：

  10.3987/com-96-7462
• 作为产物：
  描述：

  2-methylsulfanyl-indolizine-1-carboxylic acid amide 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氯化亚砜 、 硫酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 210.0h， 生成 [5-Methylsulfanyl-6-(sulfanylmethyl)-11-azatricyclo[5.3.1.04,11]undeca-1,3,5,7,9-pentaen-2-yl]methanethiol
  参考文献：
  名称：

  Synthesis of 2,12-Dithia[3](2,6)pyridino[3](1,4)cycl[3.2.2]azinophane and It's Barrier to Methylene Twist

  摘要：

  A synthesis of the title compound (11) is completed starting from indolizine (3). Key intermediate, bis(mercaptomethyl)cycl[3.2.2]azine (9) has been synthesized by reduction of bis(acetylthiomethyl)cycl[3.2.2]azine (8) with LiAlH4. 2, 12-Dithia[3] (2,6)pyridino[3](1,4)cycl[3.2.2]azinophanes (11a,b) have been synthesized by the reaction of 9 with 2,6-bis(bromomethyl)pyridine (10) in the presence of Cs2CO3 by the high dilution method. In the H-1-nmr spectrum of 11a,b, these exist in the syn conformation in their H-1-nmr spectra With regard to 2, 12-dithia[3](2,6)pyridino[3](1,4)cycl[3.2.2]azinophane (11a), the coalescence temperature for the methylene twist yields an activation barrier, Delta G(double dagger), of 79.5 ki mol(-1) for variable temperature (VT) nmr method.

  DOI：

  10.3987/com-96-7462

文献信息

• A New Synthesis of 2,12-Dithia[3.3](1,4)cycl[3.2.2]azinophanes
  作者：Yoshiro Matsuda、Hiromi Gotou、Keisuke Katou、Hiroshi Matsumoto、Makoto Yamashita、Kimitoshi Takahashi、Shizuki Ide

  DOI：10.3987/com-90-5368

  日期：——
• MATSUDA, YOSHIRO;GOTOU, HIROMI;KATOU, KEISUKE;MATSUMOTO, HIROSHI;YAMASHIT+, HETEROCYCLES, 31,(1990) N, C. 983-986
  作者：MATSUDA, YOSHIRO、GOTOU, HIROMI、KATOU, KEISUKE、MATSUMOTO, HIROSHI、YAMASHIT+

  DOI：——

  日期：——