3-(3,6-dihydro-2-methylsulfanylthiapyran-2-yl)pyridine | 882661-63-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 3-(3,6-dihydro-2-methylsulfanylthiapyran-2-yl)pyridine
• 英文别名: 3-(6-Methylsulfanyl-2,5-dihydrothiopyran-6-yl)pyridine
• CAS: 882661-63-4
• 化学式: C₁₁H₁₃NS₂
• 分子量: 223.363
• InChiKey: USOBSINOGBIHHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,6-dihydro-2-methylsulfanylthiapyran-2-yl)pyridine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 2.0h， 以75%的产率得到3-(3,6-dihydro-2H-thiapyran-2-yl)pyridine
  参考文献：
  名称：

  Pyridinedithioesters as Heterodienophiles:  Application to the Synthesis of Aprikalim

  摘要：

  Pyridinedithioesters can be used as efficient heterodienophiles when activated by complexation with BF3, by protonation, or by oxidation of the nitrogen atom of the pyridine moiety. The hetero-Diels-Alder reaction using 3-pyridinedithioester as a heterodienophile was the key step in a new synthesis of Aprikalim in racemic form. The methodology can be reliably extended to prepare new analogues of Aprikalim.

  DOI：

  10.1021/ol052942k
• 作为产物：
  描述：

  1,3-丁二烯 、 methyl pyridine-3-carbodithioate 在 盐酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 以78%的产率得到3-(3,6-dihydro-2-methylsulfanylthiapyran-2-yl)pyridine
  参考文献：
  名称：

  Pyridinedithioesters as Heterodienophiles:  Application to the Synthesis of Aprikalim

  摘要：

  Pyridinedithioesters can be used as efficient heterodienophiles when activated by complexation with BF3, by protonation, or by oxidation of the nitrogen atom of the pyridine moiety. The hetero-Diels-Alder reaction using 3-pyridinedithioester as a heterodienophile was the key step in a new synthesis of Aprikalim in racemic form. The methodology can be reliably extended to prepare new analogues of Aprikalim.

  DOI：

  10.1021/ol052942k

文献信息

• Org. Lett. 2006, 8, 1033-1036
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 1992,35, 3613-3624
  作者：

  DOI：——

  日期：——
• Pyridinedithioesters as Heterodienophiles:  Application to the Synthesis of Aprikalim
  作者：Reyhan Bastin、Hashim Albadri、Annie-Claude Gaumont、Mihaela Gulea

  DOI：10.1021/ol052942k

  日期：2006.3.1

  Pyridinedithioesters can be used as efficient heterodienophiles when activated by complexation with BF3, by protonation, or by oxidation of the nitrogen atom of the pyridine moiety. The hetero-Diels-Alder reaction using 3-pyridinedithioester as a heterodienophile was the key step in a new synthesis of Aprikalim in racemic form. The methodology can be reliably extended to prepare new analogues of Aprikalim.