3,5-Dibromo-4-methoxymethoxymethyl-pyridine | 197007-95-7

• 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: 3,5-Dibromo-4-methoxymethoxymethyl-pyridine
• 英文别名: 3,5-Dibromo-4-(methoxymethoxymethyl)pyridine
• CAS: 197007-95-7
• 化学式: C₈H₉Br₂NO₂
• 分子量: 310.973
• InChiKey: XYEDVHUKHLYGTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  3,5-Dibromo-4-methoxymethoxymethyl-pyridine 在 正丁基锂 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.5h， 以33%的产率得到3,5-difluoro-4-methoxymethoxymethyl-pyridine
  参考文献：
  名称：

  Synthesis of difluorinated pyridinecarboxaldehyde via electrophilic fluorination

  摘要：

  An efficient synthesis of novel 3,5-difluoropyridine-4-carboxaldehyde using N-fluoro-benzenesulfonimide (NSFi) is described. Difluorination was achieved through the reaction of 3,5-dihalo-1,3-dioxolane pyridine with n-butyllithium followed by N-fluorobenzenesulfonimide at -120 degrees C in good to high yields. Maintaining the low temperature during the transmetallation was found to be critical for the selective formation of the difluoro-susbstitution over the monofluoro one. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.02.009
• 作为产物：
  描述：

  氯甲基甲基醚 、 (3,5-二溴吡啶-4-基)甲醇 生成 3,5-Dibromo-4-methoxymethoxymethyl-pyridine
  参考文献：
  名称：

  Synthesis of difluorinated pyridinecarboxaldehyde via electrophilic fluorination

  摘要：

  An efficient synthesis of novel 3,5-difluoropyridine-4-carboxaldehyde using N-fluoro-benzenesulfonimide (NSFi) is described. Difluorination was achieved through the reaction of 3,5-dihalo-1,3-dioxolane pyridine with n-butyllithium followed by N-fluorobenzenesulfonimide at -120 degrees C in good to high yields. Maintaining the low temperature during the transmetallation was found to be critical for the selective formation of the difluoro-susbstitution over the monofluoro one. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.02.009

文献信息

• Synthesis of 4-alkyl-3,5-dibromo-, 3-bromo-4,5-dialkyl- and 3,4,5-trialkylpyridines via sequential metalation and metal-halogen exchange of 3,5-dibromopyridine
  作者：Yu Gui Gu、Erol K. Bayburt

  DOI：10.1016/0040-4039(96)00331-0

  日期：1996.4

  Lithiation of 3,5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3,5-dibromopyridines 2 in high yield. 3-Bromo-4,5-dialkylpyridines 3 were synthesized by metal-halogen exchange of 2 with one equivalent n-BuLi and reaction with a second electrophile. Further metal-halogen exchange of 3 and reaction with a third electrophile provided 3,4,5-trisubstituted pyridines

  3，5-二溴吡啶与LDA的锂化以及随后与亲电试剂的反应以高收率提供了4-烷基-3，5-二溴吡啶2。3-溴-4,5- dialkylpyridines 3通过金属-卤素交换合成2用一级当量的n-BuLi并反应与第二电试剂。的另外的金属-卤素交换3和反应与第三电子试剂提供3,4,5-三取代的吡啶4。
• US5668141A
  申请人：——

  公开号：US5668141A

  公开（公告）日：1997-09-16