2-(6-chlorohexyl)-pyridine | 237763-53-0

• 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: 2-(6-chlorohexyl)-pyridine
• 英文别名: 2-(6-chlorohexyl)pyridine
• CAS: 237763-53-0
• 化学式: C₁₁H₁₆ClN
• 分子量: 197.708
• InChiKey: KBXDBMUZODVBPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  二异丙基磷化氢 、 2-(6-chlorohexyl)-pyridine 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.0h， 以89%的产率得到2-(6-diisopropylphosphino-hexyl)-pyridine
  参考文献：
  名称：

  Synthesis of Hemilabile P,N Ligands: ω-2-Pyridyl-n-alkylphosphines

  摘要：

  A series of P,N ligands of the general formula (2-py)-(CH2)(n)-PR2 (2-py: 2-pyridyl; R: i-Pr (n = 1, 4-7), Ph (n = 5-7)) 4a-g and 6a has been synthesized. Starting from 2-picoline (1), 2-(omega-chloroalkyl)pyridines 3a-d are prepared. The reactions of 3a-d with (i-Pr)(2)PLi and Ph2PLi, respectively, result in the title compounds 4a-g in up to 89% yield. Reaction of Cl-(CH2)(3)-P(i-Pr)(2) with 2-picolyllithium (2) is an alternative route to 4a. Additionally, P,P,N ligands 7a and 9 are synthesized by similar methods. All new compounds were fully characterized. The formation of cyclic pyridinium derivatives 5a and 5b from intramolecular SN reactions of 3a and 3b is discussed in detail.

  DOI：

  10.1007/pl00010260
• 作为产物：
  描述：

  碳酸甲丙酯 、 1-溴-5-氯戊烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 39.0h， 以68%的产率得到2-(6-chlorohexyl)-pyridine
  参考文献：
  名称：

  Synthesis of Hemilabile P,N Ligands: ω-2-Pyridyl-n-alkylphosphines

  摘要：

  A series of P,N ligands of the general formula (2-py)-(CH2)(n)-PR2 (2-py: 2-pyridyl; R: i-Pr (n = 1, 4-7), Ph (n = 5-7)) 4a-g and 6a has been synthesized. Starting from 2-picoline (1), 2-(omega-chloroalkyl)pyridines 3a-d are prepared. The reactions of 3a-d with (i-Pr)(2)PLi and Ph2PLi, respectively, result in the title compounds 4a-g in up to 89% yield. Reaction of Cl-(CH2)(3)-P(i-Pr)(2) with 2-picolyllithium (2) is an alternative route to 4a. Additionally, P,P,N ligands 7a and 9 are synthesized by similar methods. All new compounds were fully characterized. The formation of cyclic pyridinium derivatives 5a and 5b from intramolecular SN reactions of 3a and 3b is discussed in detail.

  DOI：

  10.1007/pl00010260

文献信息

• Synthesis of Hemilabile P,N Ligands: ω-2-Pyridyl-n-alkylphosphines
  作者：Achim Jansen、Stephan Pitter

  DOI：10.1007/pl00010260

  日期：1999.6

  A series of P,N ligands of the general formula (2-py)-(CH2)(n)-PR2 (2-py: 2-pyridyl; R: i-Pr (n = 1, 4-7), Ph (n = 5-7)) 4a-g and 6a has been synthesized. Starting from 2-picoline (1), 2-(omega-chloroalkyl)pyridines 3a-d are prepared. The reactions of 3a-d with (i-Pr)(2)PLi and Ph2PLi, respectively, result in the title compounds 4a-g in up to 89% yield. Reaction of Cl-(CH2)(3)-P(i-Pr)(2) with 2-picolyllithium (2) is an alternative route to 4a. Additionally, P,P,N ligands 7a and 9 are synthesized by similar methods. All new compounds were fully characterized. The formation of cyclic pyridinium derivatives 5a and 5b from intramolecular SN reactions of 3a and 3b is discussed in detail.