(E)-18-Iodo-octadec-17-enoic acid methyl ester | 87640-10-6

• 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: (E)-18-Iodo-octadec-17-enoic acid methyl ester
• 英文别名: methyl (E)-18-iodooctadec-17-enoate
• CAS: 87640-10-6
• 化学式: C₁₉H₃₅IO₂
• 分子量: 422.39
• InChiKey: TXQGEWNJPXEKSL-FBMGVBCBSA-N

物化性质

• 沸点：
  422.8±18.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  22
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  油酸甲酯 在 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 硫酸 、 水 、 溴 、 chloroamine-T 、 potassium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 1,3-丙二胺 、 sodium iodide 、 儿萘酚硼烷 作用下， 以 乙醚 、 氯仿 、 丙酮 为溶剂， 反应 63.75h， 生成 (E)-18-Iodo-octadec-17-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated (E)-18-iodo-17-octadecenoic acid as a model iodoalkenyl fatty acid for myocardial imaging

  摘要：

  125I-labeled (E)-18-iodo-17-octadecenoic acid (13) has been prepared and evaluated in rats to determine the myocardial uptake and retention and degree of in vivo deiodination of this model iodovinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism. This new agent was prepared by NaI-chloramine-T treatment of (17-carbomethoxyheptadec-1-en-1-yl)boronic acid (11) prepared by catecholborane treatment of methyl 17-octadecynoate (10), followed by basic hydrolysis to the free acid (13). The pivotal substrate, 17-octadecynoic acid (9), was prepared by two new routes. The 125I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28% dose/g) with 45% washout after 2 h but lower heart/blood ratios in comparison to analogues containing the tellurium heteroatom. Deiodination was low for the first 2 h after injection (2 h, 61% dose/g). Excellent myocardial images were obtained in a dog with the 123I-labeled agent.

  DOI：

  10.1021/jm00367a021

文献信息

• Synthesis and evaluation of radioiodinated (E)-18-iodo-17-octadecenoic acid as a model iodoalkenyl fatty acid for myocardial imaging
  作者：F. F. Knapp、M. M. Goodman、G. W. Kabalka、K. A. R. Sastry

  DOI：10.1021/jm00367a021

  日期：1984.1

  125I-labeled (E)-18-iodo-17-octadecenoic acid (13) has been prepared and evaluated in rats to determine the myocardial uptake and retention and degree of in vivo deiodination of this model iodovinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism. This new agent was prepared by NaI-chloramine-T treatment of (17-carbomethoxyheptadec-1-en-1-yl)boronic acid (11) prepared by catecholborane treatment of methyl 17-octadecynoate (10), followed by basic hydrolysis to the free acid (13). The pivotal substrate, 17-octadecynoic acid (9), was prepared by two new routes. The 125I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28% dose/g) with 45% washout after 2 h but lower heart/blood ratios in comparison to analogues containing the tellurium heteroatom. Deiodination was low for the first 2 h after injection (2 h, 61% dose/g). Excellent myocardial images were obtained in a dog with the 123I-labeled agent.