2-(2-methoxyethoxy)ethyl phenylpropiolate | 1078574-74-9

• 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: 2-(2-methoxyethoxy)ethyl phenylpropiolate
• 英文别名: 2-(2-methoxyethoxy)ethyl 3-phenylprop-2-ynoate
• CAS: 1078574-74-9
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: HONDZNIHHAIYRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(2-methoxyethoxy)ethyl phenylpropiolate 在 [,14-bis(diphenylphosphino)butane] (1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 氘代丙酮 为溶剂， 以80%的产率得到2-(2-methoxyethoxy)ethyl (Z)-3-phenylprop-2-enoate
  参考文献：
  名称：

  New Hyperpolarized Contrast Agents for ¹³C-MRI from Para-Hydrogenation of Oligooxyethylenic Alkynes

  摘要：

  Two alkyne derivatives, which contain one and two oligooxyethylenic chains respectively, showed to be good substrates for para-hydrogenation reactions, yielding the corresponding hyperpolarized alkenes in good yields. A suitable theory has been developed to account for the observed results, fully explaining the different para-H-2 induced effects observed upon the para-hydrogenation of symmetrically and asymmetrically substituted alkynes in ALTADENA and PASADENA modes. The oligooxyethylenic substituent provides good water solubility to the para-hydrogenated symmetrical derivative. C-13-MR in vitro images of the latter derivative were obtained both in acetone and in water solutions (130 mM), using the ALTADENA procedure and after application of the field cycling procedure which allows acquisition of an in-phase C-13 carbonyl resonance. The finding that the hydrogenated product is water-soluble in contrast to the parent alkyne which is not allows for the pursuit of a fast phase-transfer separation from the organic solvent, the unreacted substrate, and the catalyst to obtain a "ready-to-use" water solution suitable for further in vivo MRI applications.

  DOI：

  10.1021/ja8059733
• 作为产物：
  描述：

  二乙二醇单甲醚 、 苯丙炔酸 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 反应 24.0h， 以45%的产率得到2-(2-methoxyethoxy)ethyl phenylpropiolate
  参考文献：
  名称：

  New Hyperpolarized Contrast Agents for ¹³C-MRI from Para-Hydrogenation of Oligooxyethylenic Alkynes

  摘要：

  Two alkyne derivatives, which contain one and two oligooxyethylenic chains respectively, showed to be good substrates for para-hydrogenation reactions, yielding the corresponding hyperpolarized alkenes in good yields. A suitable theory has been developed to account for the observed results, fully explaining the different para-H-2 induced effects observed upon the para-hydrogenation of symmetrically and asymmetrically substituted alkynes in ALTADENA and PASADENA modes. The oligooxyethylenic substituent provides good water solubility to the para-hydrogenated symmetrical derivative. C-13-MR in vitro images of the latter derivative were obtained both in acetone and in water solutions (130 mM), using the ALTADENA procedure and after application of the field cycling procedure which allows acquisition of an in-phase C-13 carbonyl resonance. The finding that the hydrogenated product is water-soluble in contrast to the parent alkyne which is not allows for the pursuit of a fast phase-transfer separation from the organic solvent, the unreacted substrate, and the catalyst to obtain a "ready-to-use" water solution suitable for further in vivo MRI applications.

  DOI：

  10.1021/ja8059733