2-[4-[Cyclopentylidene-(4-hydroxyphenyl)methyl]phenoxy]ethyl methanesulfonate | 1331867-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[4-[Cyclopentylidene-(4-hydroxyphenyl)methyl]phenoxy]ethyl methanesulfonate
• CAS: 1331867-58-3
• 化学式: C₂₁H₂₄O₅S
• 分子量: 388.485
• InChiKey: XHQFYFGHNZJGTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-[Cyclopentylidene-(4-hydroxyphenyl)methyl]phenoxy]ethyl methanesulfonate 在 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以30%的产率得到4-[cyclopentylidene-[4-(2-(18F)fluoranylethoxy)phenyl]methyl]phenol
  参考文献：
  名称：

  Synthesis and evaluation of fluoroethyl cyclofenil analogs: Models for potential estrogen receptor imaging agent

  摘要：

  Cyclofenil analogs (2a-2f) and their fluorine-containing derivatives (3a-3f) were synthesized and evaluated as candidate ligands for positron emission tomography (PET) imaging of estrogen receptors. Most of them show relatively high binding affinities comparable with estradiol (E-2). (4-Fluoroethoxyphenyl)-(4-hydroxyphenyl) methylenecyclopentane (3a) showed both the highest binding affinity for ERs (88.6 for ER beta, 13.8 for ER alpha) and highest beta/alpha ratio (beta/alpha for 6.4-fold). The radioactive compound [F-18]3a was prepared via displacement of the corresponding mesylate precursor 4 with [F-18]fluoride (F-18: beta(+): 96.7%, T-1/2 = 109.8 min). The biodistribution studies in immature female SD rats demonstrated that the uptake in the uterus and ovaries were 1.358 +/- 0.089% ID/g, 1.439 +/- 0.214% ID/g, respectively, both of the ratios of uterus/blood and ovaries/blood was less than 2:1. Micro-PET imaging of immature female SD rats has also been reported. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.04.005
• 作为产物：
  描述：

  4,4'-二羟基二苯甲酮 在 四氯化钛 、 potassium carbonate 、 锌 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 3.0h， 生成 2-[4-[Cyclopentylidene-(4-hydroxyphenyl)methyl]phenoxy]ethyl methanesulfonate
  参考文献：
  名称：

  Synthesis and evaluation of fluoroethyl cyclofenil analogs: Models for potential estrogen receptor imaging agent

  摘要：

  Cyclofenil analogs (2a-2f) and their fluorine-containing derivatives (3a-3f) were synthesized and evaluated as candidate ligands for positron emission tomography (PET) imaging of estrogen receptors. Most of them show relatively high binding affinities comparable with estradiol (E-2). (4-Fluoroethoxyphenyl)-(4-hydroxyphenyl) methylenecyclopentane (3a) showed both the highest binding affinity for ERs (88.6 for ER beta, 13.8 for ER alpha) and highest beta/alpha ratio (beta/alpha for 6.4-fold). The radioactive compound [F-18]3a was prepared via displacement of the corresponding mesylate precursor 4 with [F-18]fluoride (F-18: beta(+): 96.7%, T-1/2 = 109.8 min). The biodistribution studies in immature female SD rats demonstrated that the uptake in the uterus and ovaries were 1.358 +/- 0.089% ID/g, 1.439 +/- 0.214% ID/g, respectively, both of the ratios of uterus/blood and ovaries/blood was less than 2:1. Micro-PET imaging of immature female SD rats has also been reported. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.04.005