but-2-ynoic-1-13C acid | 1228048-73-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: but-2-ynoic-1-13C acid
• CAS: 1228048-73-4
• 化学式: C₄H₄O₂
• 分子量: 85.0636
• InChiKey: LUEHNHVFDCZTGL-AZXPZELESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  6.0
• 可旋转键数：
  0.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  but-2-ynoic-1-13C acid 在 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Para-hydrogenated Glucose Derivatives as Potential ¹³C-Hyperpolarized Probes for Magnetic Resonance Imaging

  摘要：

  A set of molecules in which a glucose moiety is bound to a hydrogenable synthon has been synthesized and evaluated for hydrogenation reactions and for the corresponding para-hydrogen-induced polarization (PHIP) effects, in order to select suitable candidates for an in vivo magnetic resonance imaging (MRI) method for the assessment of glucose cellular uptake. It has been found that amidic derivatives do not yield any polarization enhancement, probably due to singlet-triplet state mixing along the reaction pathway. In contrast, ester derivatives are hydrogenated in high yield and afford enhanced H-1 and C-13 NMR spectra after para-hydrogenation. The obtained PHIP patterns are discussed and explained on the basis of the calculated spin level populations in the para-hydrogenated products. These molecules may find interesting applications in C-13 MRI as hyperpolarized probes for assessing the activity of glucose transporters in cells.

  DOI：

  10.1021/ja101399q
• 作为产物：
  描述：

  二氧化碳-13C 、 丙炔 在 三苯基甲烷 、 sodium hydride 作用下， 以 二甲基亚砜 、 四氢呋喃 为溶剂， 以70%的产率得到but-2-ynoic-1-13C acid
  参考文献：
  名称：

  Para-hydrogenated Glucose Derivatives as Potential ¹³C-Hyperpolarized Probes for Magnetic Resonance Imaging

  摘要：

  A set of molecules in which a glucose moiety is bound to a hydrogenable synthon has been synthesized and evaluated for hydrogenation reactions and for the corresponding para-hydrogen-induced polarization (PHIP) effects, in order to select suitable candidates for an in vivo magnetic resonance imaging (MRI) method for the assessment of glucose cellular uptake. It has been found that amidic derivatives do not yield any polarization enhancement, probably due to singlet-triplet state mixing along the reaction pathway. In contrast, ester derivatives are hydrogenated in high yield and afford enhanced H-1 and C-13 NMR spectra after para-hydrogenation. The obtained PHIP patterns are discussed and explained on the basis of the calculated spin level populations in the para-hydrogenated products. These molecules may find interesting applications in C-13 MRI as hyperpolarized probes for assessing the activity of glucose transporters in cells.

  DOI：

  10.1021/ja101399q

文献信息

• Synthesis and testing of a p-H₂ hyperpolarized ¹³ C probe based on the pyrazolo[1,5-<i>a</i> ]pyrimidineacetamide DPA-713, an MRI vector to target the peripheral benzodiazepine receptors
  作者：Erika Cerutti、Alessandra Viale、Annelaure Damont、Frédéric Dollé、Silvio Aime

  DOI：10.1002/mrc.2839

  日期：2011.12

  carbon atom is approximately 21.9 s (at 9.37 T). A 13 C‐MR image has been acquired by using the 13 C RARE (Rapid Acquisition by Relaxation Enhancement) acquisition protocol on a 10‐mM solution. The main limitation to the in vivo use of this novel para‐hydrogenated [13 C]derivative is its relatively low solubility in aqueous systems. Copyright © 2011 John Wiley & Sons, Ltd.

  DPA-713 是最近开发的 2-苯基吡唑并 [1,5-a] 嘧啶乙酰胺系列的先导化合物，已显示出对外周苯二氮卓受体的良好靶向能力，最近更名为易位蛋白 (18 kDa) 或简称 TSPO . 在此结构的基础上，设计并合成了一种带有 [13C] 丁酸酯部分的新型衍生物（三步 - 总产率为 42%），通过快速和定量的对位氢化，提供相应的超极化 [13C] 烯烃。在 1H 和 13C-NMR 光谱中均检测到对氢诱导极化效应。在应用场循环程序后，添加对 H2 的氢的自旋顺序转移到 13 C 羧酸盐部分，产生大约 4500 倍的信号增强。羧酸盐碳原子的 T1 约为 21.9 s（在 9.37 T）。13 C-MR 图像已通过在 10 mM 溶液上使用 13 C RARE（通过松弛增强的快速采集）采集协议获得。这种新型仲氢化[ 13 C] 衍生物在体内使用的主要限制是其在水性体系中的溶解度相对较低。版权所有