methyl (2S)-3-[4-(4-hydroxyphenoxy)-3,5-diiodo(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino](1,2,3-13C3)propanoate | 1431868-07-3

• 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: methyl (2S)-3-[4-(4-hydroxyphenoxy)-3,5-diiodo(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino](1,2,3-13C3)propanoate
• CAS: 1431868-07-3
• 化学式: C₂₁H₂₃I₂NO₆
• 分子量: 649.12
• InChiKey: RJKYSDHEPDPHDA-AGAJJWMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-[4-(4-hydroxyphenoxy)-3,5-diiodo(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino](1,2,3-13C3)propanoate 在 一氯化碘 、 正丁胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以36.9%的产率得到methyl (2S)-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino](1,2,3-13C3)propanoate
  参考文献：
  名称：

  The Synthesis of ¹³C₉-¹⁵N-Labeled 3,5-Diiodothyronine and Thyroxine

  摘要：

  Thyroid hormones undergo extensive metabolism to regulate hormone activity. A labeled thyroid hormone would be useful to track hormone metabolism through various pathways. While radiolabeled thyroid hormones have been synthesized and used for in vivo studies, a stable isotope labeled form of thyroid hormone is required for studying thyroid hormone metabolism by LC-MS/MS, an analytical technique that has certain advantages without the complications of radioactivity. Here we report the synthesis of 13C9-15N-T2 and 13C9-15N-T4, two labeled thyroid hormone derivatives suitable for in vivo LC-MS/MS studies. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.639005
• 作为产物：
  描述：

  methyl (2S)-3-(4-hydroxy(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl)-2-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino](1,2,3-13C3)propanoate 在 吡啶 、 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 copper diacetate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 49.0h， 生成 methyl (2S)-3-[4-(4-hydroxyphenoxy)-3,5-diiodo(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl]-2-[(2-methylpropan-2-yl)oxycarbonyl(15N)amino](1,2,3-13C3)propanoate
  参考文献：
  名称：

  The Synthesis of ¹³C₉-¹⁵N-Labeled 3,5-Diiodothyronine and Thyroxine

  摘要：

  Thyroid hormones undergo extensive metabolism to regulate hormone activity. A labeled thyroid hormone would be useful to track hormone metabolism through various pathways. While radiolabeled thyroid hormones have been synthesized and used for in vivo studies, a stable isotope labeled form of thyroid hormone is required for studying thyroid hormone metabolism by LC-MS/MS, an analytical technique that has certain advantages without the complications of radioactivity. Here we report the synthesis of 13C9-15N-T2 and 13C9-15N-T4, two labeled thyroid hormone derivatives suitable for in vivo LC-MS/MS studies. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.639005