6-bromo-N,N-diisopropyl-4-methoxy-2,2'-bipyridine-3-carbamate | 437709-76-7

• 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: 6-bromo-N,N-diisopropyl-4-methoxy-2,2'-bipyridine-3-carbamate
• 英文别名: (6-bromo-4-methoxy-2-pyridin-2-ylpyridin-3-yl) N,N-di(propan-2-yl)carbamate
• CAS: 437709-76-7
• 化学式: C₁₈H₂₂BrN₃O₃
• 分子量: 408.295
• InChiKey: ZIFUOHTTYIGDOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-bromo-N,N-diisopropyl-4-methoxy-2,2'-bipyridine-3-carbamate 在 吡啶 、 盐酸羟胺 、 sodium methylate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 45.0h， 生成 (E)-3-hydroxy-4-methoxy-2,2'-bipyridine-6-carboxaldehyde oxime
  参考文献：
  名称：

  First Synthesis of Caerulomycin B. A New Synthesis of Caerulomycin C

  摘要：

  Caerulomycins produced by Streptomyces caeruleus are bipyridinic molecules endowed with antibiotic properties. The first synthesis of caerulomycin B (1) as well as a new synthesis of caerulomycin C (2) are reported. Starting from 3-hydroxypyridine, the same methodology was used to prepare both compounds 1 and 2. Efficiently controlled reactions such as metalation to allow the synthesis of 2,6-diiodo-3,4-dialkoxypyridines, which are key intermediates, and further halogen lithium exchange and cross-coupling to reach the targets molecules 1 and 2 have been developed.

  DOI：

  10.1021/jo010913r
• 作为产物：
  描述：

  3-羟基-4-甲氧基吡啶 在 吡啶 、 正丁基锂 、 仲丁基锂 、 苯基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 环己烷 为溶剂， 反应 27.0h， 生成 6-bromo-N,N-diisopropyl-4-methoxy-2,2'-bipyridine-3-carbamate
  参考文献：
  名称：

  First Synthesis of Caerulomycin B. A New Synthesis of Caerulomycin C

  摘要：

  Caerulomycins produced by Streptomyces caeruleus are bipyridinic molecules endowed with antibiotic properties. The first synthesis of caerulomycin B (1) as well as a new synthesis of caerulomycin C (2) are reported. Starting from 3-hydroxypyridine, the same methodology was used to prepare both compounds 1 and 2. Efficiently controlled reactions such as metalation to allow the synthesis of 2,6-diiodo-3,4-dialkoxypyridines, which are key intermediates, and further halogen lithium exchange and cross-coupling to reach the targets molecules 1 and 2 have been developed.

  DOI：

  10.1021/jo010913r

文献信息

• First Synthesis of Caerulomycin B. A New Synthesis of Caerulomycin C
  作者：Florence Mongin、François Trécourt、Bruno Gervais、Olivier Mongin、Guy Quéguiner

  DOI：10.1021/jo010913r

  日期：2002.5.1

  Caerulomycins produced by Streptomyces caeruleus are bipyridinic molecules endowed with antibiotic properties. The first synthesis of caerulomycin B (1) as well as a new synthesis of caerulomycin C (2) are reported. Starting from 3-hydroxypyridine, the same methodology was used to prepare both compounds 1 and 2. Efficiently controlled reactions such as metalation to allow the synthesis of 2,6-diiodo-3,4-dialkoxypyridines, which are key intermediates, and further halogen lithium exchange and cross-coupling to reach the targets molecules 1 and 2 have been developed.