2-Methylthio-5,6,7,8,9-pentahydrocyclohepta[2,1-b]pyridine-3-carbonitrile | 130506-73-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-Methylthio-5,6,7,8,9-pentahydrocyclohepta[2,1-b]pyridine-3-carbonitrile
• 英文别名: 2-methylsulfanyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile
• CAS: 130506-73-9
• 化学式: C₁₂H₁₄N₂S
• 分子量: 218.323
• InChiKey: PVMOBFWFZJAJJE-UHFFFAOYSA-N

物化性质

• 熔点：
  115-116 °C(Solv: ethanol (64-17-5))
• 沸点：
  353.5±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methylthio-5,6,7,8,9-pentahydrocyclohepta[2,1-b]pyridine-3-carbonitrile 在 间氯过氧苯甲酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以40%的产率得到2-Methanesulfonyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile
  参考文献：
  名称：

  A convenient synthesis of 5-deaza nonclassical antifolates: Reaction of cyanothioacetamide with sodium salts of 2-(hydroxymethylene)-1-cycloalkanones

  摘要：

  Condensation of cyanothioacetamide with sodium salts of 2-(Hydroxymethylene)-1-cycloalkanones afforded the corresponding pyridine-2(1H)-thiones 4. Compounds 4 served as a key intermediates for the synthesis of condensed 2,4-diaminopyrido[2,3-d]pyridines 7. Compounds 7 were of interest as potential inhibitors of dihydrofolate reductase.

  DOI：

  10.1016/s0040-4020(01)80745-6
• 作为产物：
  描述：

  sodium;(Z)-(2-oxocycloheptylidene)methanolate 在 sodium hydroxide 、 哌啶乙酸盐 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.17h， 生成 2-Methylthio-5,6,7,8,9-pentahydrocyclohepta[2,1-b]pyridine-3-carbonitrile
  参考文献：
  名称：

  A convenient synthesis of 5-deaza nonclassical antifolates: Reaction of cyanothioacetamide with sodium salts of 2-(hydroxymethylene)-1-cycloalkanones

  摘要：

  Condensation of cyanothioacetamide with sodium salts of 2-(Hydroxymethylene)-1-cycloalkanones afforded the corresponding pyridine-2(1H)-thiones 4. Compounds 4 served as a key intermediates for the synthesis of condensed 2,4-diaminopyrido[2,3-d]pyridines 7. Compounds 7 were of interest as potential inhibitors of dihydrofolate reductase.

  DOI：

  10.1016/s0040-4020(01)80745-6

文献信息

• Reductive desulfurization of 3-cyano-2-methylthiopyridines under the action of Raney nickel
  作者：A. A. Zubarev、V. K. Zav’yalova、V. P. Litvinov

  DOI：10.1007/s11172-006-0158-6

  日期：2005.11

  The action of Raney nickel on substituted 3-cyano-2-methylthiopyridines was studied. Under conditions of catalytic hydrogenation, the reaction yields a mixture containing the aminosulfide resulting from reduction of the nitrile group with retention of the methylthio group, the nitrile resulting from elimination of the methylthio group, and the amine resulting from both reduction of the nitrile group

  研究了雷尼镍对取代的 3-氰基-2-甲基硫代吡啶的作用。在催化加氢条件下，反应生成的混合物含有由腈基还原而保留甲硫基的氨基硫化物、由甲硫基消除的腈和由腈基和甲硫基同时还原产生的胺。消除甲硫基。在脱硫条件下用大量阮内镍处理 3-氰基-2-甲硫基吡啶可同时消除甲硫基和将腈基还原为氨基甲基。在甲醇或四氢呋喃中还原脱硫生成伯胺，而在异丙醇或乙醇中反应生成仲胺或叔胺，
• LITVINOV, V. P.;SHARANIN, YU. A.;RODINOVSKAYA, L. A.;NESTEROV, V. N.;SHKL+, CHEM. SCR., 29,(1989) N, C. 327-332
  作者：LITVINOV, V. P.、SHARANIN, YU. A.、RODINOVSKAYA, L. A.、NESTEROV, V. N.、SHKL+

  DOI：——

  日期：——
• A convenient synthesis of 5-deaza nonclassical antifolates: Reaction of cyanothioacetamide with sodium salts of 2-(hydroxymethylene)-1-cycloalkanones
  作者：Galal E.H. Elgemeie、Badria A.W. Hussain

  DOI：10.1016/s0040-4020(01)80745-6

  日期：1994.4

  Condensation of cyanothioacetamide with sodium salts of 2-(Hydroxymethylene)-1-cycloalkanones afforded the corresponding pyridine-2(1H)-thiones 4. Compounds 4 served as a key intermediates for the synthesis of condensed 2,4-diaminopyrido[2,3-d]pyridines 7. Compounds 7 were of interest as potential inhibitors of dihydrofolate reductase.