2,6-diiodo-N,N-diisopropylpyridine-3-carbamate | 437709-97-2

• 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: 2,6-diiodo-N,N-diisopropylpyridine-3-carbamate
• 英文别名: diisopropylcarbamic acid 2,6-diiodo(pyridin-3-yl) ester；(2,6-diiodopyridin-3-yl) N,N-di(propan-2-yl)carbamate
• CAS: 437709-97-2
• 化学式: C₁₂H₁₆I₂N₂O₂
• 分子量: 474.08
• InChiKey: AVEDKGSBVQWZCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-diiodo-N,N-diisopropylpyridine-3-carbamate 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 11.0h， 生成 2,6-diiodo-N,N-diisopropyl-4-methoxypyridine-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
• 作为产物：
  描述：

  2,6-二碘-3-羟基吡啶 、 二异丙基甲胺酰氯 在 吡啶 作用下， 反应 4.0h， 以70%的产率得到2,6-diiodo-N,N-diisopropylpyridine-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

• Directed Ortho Insertion (DoI):  A New Approach to Functionalized Aryl and Heteroaryl Zinc Reagents
  作者：Nadège Boudet、Shohei Sase、Pradipta Sinha、Ching-Yuan Liu、Arkady Krasovskiy、Paul Knochel

  DOI：10.1021/ja074060h

  日期：2007.10.1

  A wide range of directing groups (ester, ketone, acetate, aryl sulfonate, triazene, carbamate) allow the regioselective directed ortho insertion (DoI) of zinc in the presence of LiCl leading to polyfunctional aryl and heteroaryl zinc reagents.

  范围广泛的导向基团（酯、酮、乙酸酯、芳基磺酸盐、三氮烯、氨基甲酸酯）允许在 LiCl 存在下区域选择性定向邻位插入（DoI）锌，从而产生多官能的芳基和杂芳基锌试剂。