Synthesis of [3 H] and [14 C]Genipin.
Synthesis of [3 H] and [14 C]Genipin.
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DOI：
10.1002/jlcr.3832
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发表时间：
2020-02
影响因子：
1.8
通讯作者：
A. Queen;D. Hesk;D. Lindsay;W. Kerr;K. Rehder;T. Fennell;W. Mascarella;D. Zhong;S. Runyon
中科院分区：
文献类型：
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作者：
A. Queen;D. Hesk;D. Lindsay;W. Kerr;K. Rehder;T. Fennell;W. Mascarella;D. Zhong;S. Runyon
用Ir(I)催化氢同位素交换一步合成了京尼平。通过催化剂筛选的氘模拟研究，开发了将sp2CH键邻位选择性交换到甲酯官能团的条件。然后用氚气体合成比活度为18.5cI/mmo1的[~3H]京尼平。以[14C]氰化钾为原料，经8步反应制得外消旋[14C]京尼平，总放化产率为5.4%。
[3 H]Genipin was synthesized in a single step by Ir(I) catalyzed hydrogen isotope exchange. Conditions for selective exchange of the sp2 CH bond ortho to the methyl ester functionality were developed through deuterium modeling studies through a catalyst screen. Optimized conditions so obtained were then utilized with tritium gas to generate [3 H]genipin at a specific activity of 18.5 Ci/mmol. Racemic [14 C]genipin was prepared in 8 steps in overall 5.4% radiochemical yield from potassium [14 C]cyanide.