2-(3-氟丙基)苯酚 | 658704-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-(3-氟丙基)苯酚
• 英文名称: 2-(3-fluoropropyl)phenol
• CAS: 658704-31-5
• 化学式: C₉H₁₁FO
• 分子量: 154.184
• InChiKey: WDJGVUBJEQGHTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  237.4±20.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-氟丙基)苯酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以82%的产率得到3,4-二氢-1H-苯并吡喃
  参考文献：
  名称：

  C-F键断裂和分子内小号Ñ与O-和N-亲核试剂2反应烷基氟化物的

  摘要：

  在与O-和N-亲核试剂的分子内反应中实现了烷基氟化物的亲核取代。分子内脱氟环化反应受亲核试剂的性质，要形成的环的大小以及前体的构象刚性的影响。发现在相似的反应条件下烷基氟化物的分子间亲核取代反应是困难的。当前C-F键断裂反应的立体化学研究显示出完全的构型反转，这支持了分子内S N 2反应机理。

  DOI：

  10.1021/jo802819p
• 作为产物：
  描述：

  2-(3-hydroxypropyl)-1-[(2-methoxyethoxy)methoxy]benzene 在 盐酸 、 四丁基氟化铵 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.83h， 生成 2-(3-氟丙基)苯酚
  参考文献：
  名称：

  Synthesis and binding affinities of fluoroalkylated raloxifenes

  摘要：

  Three fluoroalkylated derivatives (1-3) of the selective estrogen receptor modulator (SERM), raloxifene, have been synthesized. The key step in the synthesis is the C-C bond formation of benzo[b]thiophene and a substituted phenyl group (ring C) using a Stille reaction. The in vitro binding affinities of the substituted raloxifenes 1-3 are 45, 60, 89%, respectively, relative to the affinity of estradiol, which is higher than the affinity of raloxifene itself (25%). When labeled with the positron-emitting radio-nuclide, these compounds might be useful as PET imaging agents for estrogen receptor-positive breast tumors. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00362-6

文献信息

• Synthesis, Radiosynthesis, and Biological Evaluation of Carbon-11 and Fluorine-18 Labeled Reboxetine Analogues: Potential Positron Emission Tomography Radioligands for in Vivo Imaging of the Norepinephrine Transporter
  作者：Fanxing Zeng、Jiyoung Mun、Nachwa Jarkas、Jeffrey S. Stehouwer、Ronald J. Voll、Gilles D. Tamagnan、Leonard Howell、John R. Votaw、Clinton D. Kilts、Charles B. Nemeroff、Mark M. Goodman

  DOI：10.1021/jm800817h

  日期：2009.1.8

  Reboxetine analogues with methyl and fluoroalkyl substituents at position 2 of the phenoxy ring 1-4 were synthesized. In vitro competition binding with [H-3]nisoxetine demonstrated that 1-4 have a high affinity for the norepinephrine transporter (NET) with K-i's = 1.02, 3.14, 3.68, and 0.30 nM, respectively. MicroPET imaging in rhesus monkeys showed that the relative regional distribution of [C-11]1 and [C-11]4 is consistent with distribution of the NET in the brain, while [F-18]2 and [F-18]3 showed only slight regional differentiation in brain uptake. Especially, the highest ratios of uptake of [C-11]1in NET-rich regions to that in caudate were obtained at 1.30-1.45 at 45 min and remained relatively constant over 85 min. Pretreatment of the monkey with the selective NET inhibitor, desipramine, decreased the specific binding for both ["C]l and [C-11]4. PET imaging in awake monkeys suggested that anesthesia influenced the binding potential of [C-11]1 and [C-11]4 at the NET.
• C−F Bond Cleavage by Intramolecular S_N2 Reaction of Alkyl Fluorides with O- and N-Nucleophiles
  作者：Laijun Zhang、Wei Zhang、Jun Liu、Jinbo Hu

  DOI：10.1021/jo802819p

  日期：2009.4.3

  The nucleophilic substitution of alkyl fluorides was achieved in the intramolecular reactions with O- and N-nucleophiles. The intramolecular defluorinative cyclization reaction was influenced by the nature of nucleophiles, the size of the ring to be formed, and the comformational rigidity of the precursors. Intermolecular nucleophilic substitution reactions of alkyl fluorides under similar reaction

  在与O-和N-亲核试剂的分子内反应中实现了烷基氟化物的亲核取代。分子内脱氟环化反应受亲核试剂的性质，要形成的环的大小以及前体的构象刚性的影响。发现在相似的反应条件下烷基氟化物的分子间亲核取代反应是困难的。当前C-F键断裂反应的立体化学研究显示出完全的构型反转，这支持了分子内S N 2反应机理。
• Synthesis and binding affinities of fluoroalkylated raloxifenes
  作者：Kyo Chul Lee、Byung Seok Moon、Jae Hak Lee、Kyoo-Hyun Chung、John A Katzenellenbogen、Dae Yoon Chi

  DOI：10.1016/s0968-0896(03)00362-6

  日期：2003.8

  Three fluoroalkylated derivatives (1-3) of the selective estrogen receptor modulator (SERM), raloxifene, have been synthesized. The key step in the synthesis is the C-C bond formation of benzo[b]thiophene and a substituted phenyl group (ring C) using a Stille reaction. The in vitro binding affinities of the substituted raloxifenes 1-3 are 45, 60, 89%, respectively, relative to the affinity of estradiol, which is higher than the affinity of raloxifene itself (25%). When labeled with the positron-emitting radio-nuclide, these compounds might be useful as PET imaging agents for estrogen receptor-positive breast tumors. (C) 2003 Elsevier Ltd. All rights reserved.