3-bromo-2-cyclohexylisonicotinonitrile | 1246461-86-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-bromo-2-cyclohexylisonicotinonitrile
• 英文别名: 3-Bromo-2-cyclohex-2-en-1-ylpyridine-4-carbonitrile；3-bromo-2-cyclohex-2-en-1-ylpyridine-4-carbonitrile
• CAS: 1246461-86-8
• 化学式: C₁₂H₁₁BrN₂
• 分子量: 263.137
• InChiKey: JOOAGRSFZGCTIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-2-cyclohexylisonicotinonitrile 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以67%的产率得到3-bromo-2-(cyclohex-2-en-1-yl)-5-iodoisonicotinonitrile
  参考文献：
  名称：

  Selective and Multiple Functionalization of Pyridines and Alkaloids via Mg- and Zn-Organometallic Intermediates

  摘要：

  Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF3 center dot OEt2. A full pyridine functionalization of all five positions of the pyridine ring can be realized by using an appropriate combination of IMP bases in the presence or absence of BF3 center dot OEt2.

  DOI：

  10.1021/ol200563j
• 作为产物：
  描述：

  4-氰基吡啶 在 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 bis(2,2,6,6-tetramethylpiperidinyl)zinc, lithium chloride, magnesium chloride complex 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 3-bromo-2-cyclohexylisonicotinonitrile
  参考文献：
  名称：

  Selective and Multiple Functionalization of Pyridines and Alkaloids via Mg- and Zn-Organometallic Intermediates

  摘要：

  Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF3 center dot OEt2. A full pyridine functionalization of all five positions of the pyridine ring can be realized by using an appropriate combination of IMP bases in the presence or absence of BF3 center dot OEt2.

  DOI：

  10.1021/ol200563j

文献信息

• Highly Selective Metalations of Pyridines and Related Heterocycles Using New Frustrated Lewis Pairs or tmp-Zinc and tmp-Magnesium Bases with BF3⋅OEt2
  作者：Milica Jaric、Benjamin A. Haag、Andreas Unsinn、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1002/anie.201002031

  日期：——

  Efficient and selective: Frustrated Lewis pairs based on BF3⋅OEt2 and LiCl‐complexed tmpMg or tmpZn amides (tmp=2,2,6,6‐tetramethylpiperidyl) allow the efficient and regioselective metalation of various functionalized N heterocycles (see scheme for examples). Moreover, such metalations carried out in the presence or absence of BF3⋅OEt2 enable a complete switch of regioselectivity, thus allowing complementary

  有效的和选择性的：基于BF沮丧路易斯对3 ⋅OEt 2和LiCl-络合tmpMg或tmpZn酰胺（TMP = 2,2,6,6-四甲基）允许各种官能化的N-杂环的高效和区域选择性金属化（参见方案用于例子）。此外，在存在或不存在BF 3· OEt 2的情况下进行的这种金属化能够完全切换区域选择性，从而允许互补的官能化。
• Selective and Multiple Functionalization of Pyridines and Alkaloids <i>via</i> Mg- and Zn-Organometallic Intermediates
  作者：Milica Jaric、Benjamin A. Haag、Sophia M. Manolikakes、Paul Knochel

  DOI：10.1021/ol200563j

  日期：2011.5.6

  Quinine, nicotine, and related electron-rich amino-substituted pyridines were readily metalated using LiCl-solubilized TMP (2,2,6,6-tetramethylpiperidyl) bases in the presence of BF3 center dot OEt2. A full pyridine functionalization of all five positions of the pyridine ring can be realized by using an appropriate combination of IMP bases in the presence or absence of BF3 center dot OEt2.