| 1374686-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• CAS: 1374686-01-7
• 化学式: C₇H₈BF₃LiN
• 分子量: 180.894
• InChiKey: ZHYMFGYDUPJEIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  在 selenium 作用下， 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Synthesis, characterization and X-ray structure of 3,4-lutidinyl-, 3-/4-picolyl- and pyridylselenium compounds

  摘要：

  Bis(4,5-dimethyl-2-pyridyl)-, bis(5-methyl-2-pyridyl)- and bis(4-methyl-2-pyridyl) diselenide have been synthesized directly from 3,4-lutidine (1a), 3-picoline (1b) and 4-picoline (1c) respectively via BF3 aided lithiation reaction. The lithiation of 3,4-lutidinium-, 3- and 4-picolinium-BF3 adduct (2a/2b/2c) gives the corresponding carbanion (3a/3b/3c) which on subjecting to selenium insertion reaction followed by aerial oxidation affords the related diselenide in good yield. Reaction of BF3 complexed pyridylselenolate anion (4a/4b/4c) with diiodomethane gives the corresponding bis(2-pyridylseleno)methane. The dilithiation of 4-picolinium-/pyridinium-BF3 adduct (2c/2d) followed by reaction with 2.2 equiv. of selenium and iodomethane affords the related 2,6-bis(methylselenenyl)pyridine and 2-(methylselenenyl)pyridine in varying proportions. Preparation of tris(methylselenenyl) derivatives of 1a and 1c have been given in the present study. LiAlH4 has also been utilized to synthesize unsymmetrical monoselenides from the corresponding diselenides. Single crystal X-ray studies of bis(4,5-dimethyl-2-pyridyl) diselenide (5a), 3,4-dimethyl-2,6-bis(methylselenenyl)pyridine (9a), 4-methyl-2,6-bis(methylselenenyl)pyridine (9c), 2,6-bis(methylselenenyl)pyridine (9d) and 4-methyl-2,6-bis(methylselenenyl)-4-(methylselenenylmethyl)pyridine (12a) have also been carried out. The crystal data of these compounds reveals that the instances of Se center dot center dot center dot Se secondary interactions decreases with the increase in the number of methyl group attached to the pyridine ring. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.03.043
• 作为产物：
  描述：

  3,4-二甲基吡啶 在 三氟化硼乙醚 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Synthesis, characterization and X-ray structure of 3,4-lutidinyl-, 3-/4-picolyl- and pyridylselenium compounds

  摘要：

  Bis(4,5-dimethyl-2-pyridyl)-, bis(5-methyl-2-pyridyl)- and bis(4-methyl-2-pyridyl) diselenide have been synthesized directly from 3,4-lutidine (1a), 3-picoline (1b) and 4-picoline (1c) respectively via BF3 aided lithiation reaction. The lithiation of 3,4-lutidinium-, 3- and 4-picolinium-BF3 adduct (2a/2b/2c) gives the corresponding carbanion (3a/3b/3c) which on subjecting to selenium insertion reaction followed by aerial oxidation affords the related diselenide in good yield. Reaction of BF3 complexed pyridylselenolate anion (4a/4b/4c) with diiodomethane gives the corresponding bis(2-pyridylseleno)methane. The dilithiation of 4-picolinium-/pyridinium-BF3 adduct (2c/2d) followed by reaction with 2.2 equiv. of selenium and iodomethane affords the related 2,6-bis(methylselenenyl)pyridine and 2-(methylselenenyl)pyridine in varying proportions. Preparation of tris(methylselenenyl) derivatives of 1a and 1c have been given in the present study. LiAlH4 has also been utilized to synthesize unsymmetrical monoselenides from the corresponding diselenides. Single crystal X-ray studies of bis(4,5-dimethyl-2-pyridyl) diselenide (5a), 3,4-dimethyl-2,6-bis(methylselenenyl)pyridine (9a), 4-methyl-2,6-bis(methylselenenyl)pyridine (9c), 2,6-bis(methylselenenyl)pyridine (9d) and 4-methyl-2,6-bis(methylselenenyl)-4-(methylselenenylmethyl)pyridine (12a) have also been carried out. The crystal data of these compounds reveals that the instances of Se center dot center dot center dot Se secondary interactions decreases with the increase in the number of methyl group attached to the pyridine ring. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.03.043

文献信息

• Synthesis, characterization and X-ray structure of 3,4-lutidinyl-, 3-/4-picolyl- and pyridylselenium compounds
  作者：Jaspreet S. Dhau、Amritpal Singh、Avtar Singh、Balwinder S. Sooch、Paula Brandão、Vítor Félix

  DOI：10.1016/j.ica.2012.03.043

  日期：2012.9

  Bis(4,5-dimethyl-2-pyridyl)-, bis(5-methyl-2-pyridyl)- and bis(4-methyl-2-pyridyl) diselenide have been synthesized directly from 3,4-lutidine (1a), 3-picoline (1b) and 4-picoline (1c) respectively via BF3 aided lithiation reaction. The lithiation of 3,4-lutidinium-, 3- and 4-picolinium-BF3 adduct (2a/2b/2c) gives the corresponding carbanion (3a/3b/3c) which on subjecting to selenium insertion reaction followed by aerial oxidation affords the related diselenide in good yield. Reaction of BF3 complexed pyridylselenolate anion (4a/4b/4c) with diiodomethane gives the corresponding bis(2-pyridylseleno)methane. The dilithiation of 4-picolinium-/pyridinium-BF3 adduct (2c/2d) followed by reaction with 2.2 equiv. of selenium and iodomethane affords the related 2,6-bis(methylselenenyl)pyridine and 2-(methylselenenyl)pyridine in varying proportions. Preparation of tris(methylselenenyl) derivatives of 1a and 1c have been given in the present study. LiAlH4 has also been utilized to synthesize unsymmetrical monoselenides from the corresponding diselenides. Single crystal X-ray studies of bis(4,5-dimethyl-2-pyridyl) diselenide (5a), 3,4-dimethyl-2,6-bis(methylselenenyl)pyridine (9a), 4-methyl-2,6-bis(methylselenenyl)pyridine (9c), 2,6-bis(methylselenenyl)pyridine (9d) and 4-methyl-2,6-bis(methylselenenyl)-4-(methylselenenylmethyl)pyridine (12a) have also been carried out. The crystal data of these compounds reveals that the instances of Se center dot center dot center dot Se secondary interactions decreases with the increase in the number of methyl group attached to the pyridine ring. (C) 2012 Elsevier B. V. All rights reserved.