3-ethynyl-6-hydroxycyclohex-2-enone | 1393657-12-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethynyl-6-hydroxycyclohex-2-enone
• 英文别名: 3-Ethynyl-6-hydroxycyclohex-2-en-1-one
• CAS: 1393657-12-9
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: VTFQHOJAHSGKCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-ethynyl-6-hydroxycyclohex-2-enone 在 吡啶 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.84h， 生成 (E)-6-fluoro-3-(pyridin-2-ylethynyl)cyclohex-2-enone O-ethyl oxime
  参考文献：
  名称：

  Synthesis and Evaluation of Novel α-Fluorinated (E)-3-((6-Methylpyridin-2-yl)ethynyl)cyclohex-2-enone-O-methyl Oxime (ABP688) Derivatives as Metabotropic Glutamate Receptor Subtype 5 PET Radiotracers

  摘要：

  In the search for an optimal fluorine-18-labeled positron emission tomography (PET) radiotracer for imaging metabotropic glutamate receptor subtype 5 (mGluRS), we have prepared a series of five alpha-fluorinated derivatives based on the ABP688 structural manifold by application of a two-step enolization/NFSI a-fluorination method. Their binding affinities were evaluated in vitro, and the most promising candidate (Z)-16 exhibited a K-i of 5.7 nM and a clogP value of 2.3. The synthesis of the precursor tosylate (E)-22 revealed a preference for the (E)-configurational isomer (K-i = 31.2 nM), and successful radiosynthesis afforded (E)-[F-18]-16 which was used as a model PET tracer to establish plasma and PBS stability. (E)-[F-18]-16 (K-d = 70 nM) exhibited excellent specificity for mGluRS in autoradiographic studies on horizontal rat brain slices in vitro.

  DOI：

  10.1021/jm300648b
• 作为产物：
  描述：

  trimethyl((3-((trimethylsilyl)ethynyl)-7-oxabicyclo[4.1.0]hept-2-en-1-yl)oxy)silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以106 mg的产率得到3-ethynyl-6-hydroxycyclohex-2-enone
  参考文献：
  名称：

  Synthesis and Evaluation of Novel α-Fluorinated (E)-3-((6-Methylpyridin-2-yl)ethynyl)cyclohex-2-enone-O-methyl Oxime (ABP688) Derivatives as Metabotropic Glutamate Receptor Subtype 5 PET Radiotracers

  摘要：

  In the search for an optimal fluorine-18-labeled positron emission tomography (PET) radiotracer for imaging metabotropic glutamate receptor subtype 5 (mGluRS), we have prepared a series of five alpha-fluorinated derivatives based on the ABP688 structural manifold by application of a two-step enolization/NFSI a-fluorination method. Their binding affinities were evaluated in vitro, and the most promising candidate (Z)-16 exhibited a K-i of 5.7 nM and a clogP value of 2.3. The synthesis of the precursor tosylate (E)-22 revealed a preference for the (E)-configurational isomer (K-i = 31.2 nM), and successful radiosynthesis afforded (E)-[F-18]-16 which was used as a model PET tracer to establish plasma and PBS stability. (E)-[F-18]-16 (K-d = 70 nM) exhibited excellent specificity for mGluRS in autoradiographic studies on horizontal rat brain slices in vitro.

  DOI：

  10.1021/jm300648b

文献信息

• Synthesis and Evaluation of Novel α-Fluorinated (<i>E</i>)-3-((6-Methylpyridin-2-yl)ethynyl)cyclohex-2-enone-<i>O</i>-methyl Oxime (ABP688) Derivatives as Metabotropic Glutamate Receptor Subtype 5 PET Radiotracers
  作者：Selena Milicevic Sephton、Linjing Mu、W. Bernd Schweizer、Roger Schibli、Stefanie D. Krämer、Simon M. Ametamey

  DOI：10.1021/jm300648b

  日期：2012.8.23

  In the search for an optimal fluorine-18-labeled positron emission tomography (PET) radiotracer for imaging metabotropic glutamate receptor subtype 5 (mGluRS), we have prepared a series of five alpha-fluorinated derivatives based on the ABP688 structural manifold by application of a two-step enolization/NFSI a-fluorination method. Their binding affinities were evaluated in vitro, and the most promising candidate (Z)-16 exhibited a K-i of 5.7 nM and a clogP value of 2.3. The synthesis of the precursor tosylate (E)-22 revealed a preference for the (E)-configurational isomer (K-i = 31.2 nM), and successful radiosynthesis afforded (E)-[F-18]-16 which was used as a model PET tracer to establish plasma and PBS stability. (E)-[F-18]-16 (K-d = 70 nM) exhibited excellent specificity for mGluRS in autoradiographic studies on horizontal rat brain slices in vitro.