(S)-N-(3,4-dihydroxyphenethyl)pyrrolidine-2-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-N-(3,4-dihydroxyphenethyl)pyrrolidine-2-carboxamide
• 英文别名: (2S)-N-[2-(3,4-dihydroxyphenyl)ethyl]pyrrolidine-2-carboxamide
• 化学式: C₁₃H₁₈N₂O₃
• 分子量: 250.298
• InChiKey: LFSHYUYUPJSRCH-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  81.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[N'-(tert-butoxycarbonyl)-L-prolyl]-dopamine 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 (S)-N-(3,4-dihydroxyphenethyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Synthesis of Isotopically Modified Derivatives of Dopamine, Serotonin, and Doxorubicin with Boc-Pro and Boc-[2H]Pro

  摘要：

  Boc-Pro-Dox, Boc-Pro-DOPA, Boc-Pro-Srt, and Pro-Dox, Pro-DOPA, Pro-Srt, as well as Boc-[H-2]Pro-Dox, Boc-[H-2]Pro-DOPA, Boc-[H-2]Pro-Srt, and [H-2]Pro-Dox, [H-2]Pro-DOPA, [H-2]Pro-Srt have been synthesized for the first time. Boc-[H-2]Pro is the most promising reagent for the preparation of deuterated compounds. The hydrogenation of Boc-Pro in ethyl acetate on palladium catalyst has allowed the introduction of deuterium by a factor of 1.6-1.65 larger than by the hydrogenation of unsaturated proline bound to serotonin and by a factor of three larger than by the hydrogenation of unsaturated proline bound to dopamine. Due to doxorubicin instability under conditions of unsaturated proline hydrogenation, its condensation with Boc-[H-2]Pro is the sole possibility to prepare Boc-[H-2]Pro-Dox. The content of isotopomers in the deuterated products has been determined by mass spectrometry.

  DOI：

  10.1134/s0012500819030030

文献信息

• Immobilized Pd on magnetic nanoparticles bearing proline as a highly efficient and retrievable Suzuki–Miyaura catalyst in aqueous media
  作者：E. Nehlig、B. Waggeh、N. Millot、Y. Lalatonne、L. Motte、E. Guénin

  DOI：10.1039/c4dt02899f

  日期：——

  Immobilized Pd on magnetic nanoparticles bearing proline as a highly efficient and retrievable Suzuki–Miyaura catalyst in aqueous media.

  在水介质中，携带脯氨酸的磁性纳米颗粒上固定的Pd是一种高效可回收的Suzuki-Miyaura催化剂。
• Synthesis of Isotopically Modified Derivatives of Dopamine, Serotonin, and Doxorubicin with Boc-Pro and Boc-[2H]Pro
  作者：V. P. Shevchenko、L. A. Andreeva、I. Yu. Nagaev、N. F. Myasoedov

  DOI：10.1134/s0012500819030030

  日期：2019.3

  Boc-Pro-Dox, Boc-Pro-DOPA, Boc-Pro-Srt, and Pro-Dox, Pro-DOPA, Pro-Srt, as well as Boc-[H-2]Pro-Dox, Boc-[H-2]Pro-DOPA, Boc-[H-2]Pro-Srt, and [H-2]Pro-Dox, [H-2]Pro-DOPA, [H-2]Pro-Srt have been synthesized for the first time. Boc-[H-2]Pro is the most promising reagent for the preparation of deuterated compounds. The hydrogenation of Boc-Pro in ethyl acetate on palladium catalyst has allowed the introduction of deuterium by a factor of 1.6-1.65 larger than by the hydrogenation of unsaturated proline bound to serotonin and by a factor of three larger than by the hydrogenation of unsaturated proline bound to dopamine. Due to doxorubicin instability under conditions of unsaturated proline hydrogenation, its condensation with Boc-[H-2]Pro is the sole possibility to prepare Boc-[H-2]Pro-Dox. The content of isotopomers in the deuterated products has been determined by mass spectrometry.