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 | 1431868-03-9

• 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-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
• CAS: 1431868-03-9
• 化学式: C₁₅H₂₁NO₅
• 分子量: 305.23
• InChiKey: NQIFXJSLCUJHBB-PJJJSQGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  [U-13C, 15N]-L-tyrosine 在 盐酸 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 生成 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
  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

文献信息

• The Synthesis of ¹³C₉-¹⁵N-Labeled 3,5-Diiodothyronine and Thyroxine
  作者：Sarah A. Hackenmueller、Thomas S. Scanlan

  DOI：10.1080/00397911.2011.639005

  日期：2013.5.15

  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.