2-[2-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]-pyridine | 1422450-63-2

• 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-[2-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]-pyridine
• 英文别名: 2-[2-Benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyridine；2-[2-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyridine
• CAS: 1422450-63-2
• 化学式: C₂₁H₂₈BNO₂
• 分子量: 337.27
• InChiKey: HAEVCPQAWSMBAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]-pyridine 在 sodium peroxoborate tetrahydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以24.5 mg的产率得到2-benzyl-3-(pyridin-2-yl)propan-1-ol
  参考文献：
  名称：

  Synthesis of Primary and Secondary Alkylboronates through Site-Selective C(sp³)–H Activation with Silica-Supported Monophosphine–Ir Catalysts

  摘要：

  The site-selective activation and borylation of unactivated C(sp(3))-H bonds in 2-alkylpyridines to form primary and secondary alkylboronates was achieved using silica-supported monophosphine-Ir catalysts. This borylation occurs selectively at C-H bonds located gamma to the pyridine nitrogen atom. The site-selectivity of this reaction suggests that the C-H bond cleavage occurs with the assistance of a proximity effect due to N-to-Ir coordination.

  DOI：

  10.1021/ja3126239
• 作为产物：
  描述：

  溴氯甲烷 、 2-[3-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]pyridine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.58h， 生成 2-[2-benzyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]-pyridine
  参考文献：
  名称：

  Synthesis of Primary and Secondary Alkylboronates through Site-Selective C(sp³)–H Activation with Silica-Supported Monophosphine–Ir Catalysts

  摘要：

  The site-selective activation and borylation of unactivated C(sp(3))-H bonds in 2-alkylpyridines to form primary and secondary alkylboronates was achieved using silica-supported monophosphine-Ir catalysts. This borylation occurs selectively at C-H bonds located gamma to the pyridine nitrogen atom. The site-selectivity of this reaction suggests that the C-H bond cleavage occurs with the assistance of a proximity effect due to N-to-Ir coordination.

  DOI：

  10.1021/ja3126239

文献信息

• Synthesis of Primary and Secondary Alkylboronates through Site-Selective C(sp³)–H Activation with Silica-Supported Monophosphine–Ir Catalysts
  作者：Soichiro Kawamorita、Ryo Murakami、Tomohiro Iwai、Masaya Sawamura

  DOI：10.1021/ja3126239

  日期：2013.2.27

  The site-selective activation and borylation of unactivated C(sp(3))-H bonds in 2-alkylpyridines to form primary and secondary alkylboronates was achieved using silica-supported monophosphine-Ir catalysts. This borylation occurs selectively at C-H bonds located gamma to the pyridine nitrogen atom. The site-selectivity of this reaction suggests that the C-H bond cleavage occurs with the assistance of a proximity effect due to N-to-Ir coordination.