3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-ol | 742699-17-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-ol
• CAS: 742699-17-8
• 化学式: C₁₆H₁₃FO₂
• 分子量: 256.276
• InChiKey: MHOHQGBZUCAPAO-UHFFFAOYSA-N

物化性质

• 沸点：
  403.9±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-ol 在 manganese(IV) oxide 作用下， 以 四氢呋喃 为溶剂， 以88 %的产率得到3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-one
  参考文献：
  名称：

  rintodestran (G1T48) 的硒类似物作为有效的雌激素受体调节剂和下调剂

  摘要：

  靶向治疗是对抗癌症的现代方向之一。如今，选择性雌激素受体调节剂（SERM）和下调剂（SERD）被用作雌激素受体阳性（ER+）肿瘤的一线治疗方法。在此，我们报告了 7 种新型苯并硒吩的设计和合成，及其 ER-α 结合活性和细胞毒性。TR-FRET竞争性ER-α结合实验表明，( E )-3-(4-((6-羟基-2-(4-羟基苯甲酰基)苯并[ b ]硒酚-3-基)氧基)苯基)丙烯酸酸 ( 21b ) 是一种比广为人知的 SERM 药物雷洛昔芬 (IC 50 = 1.78 nM)更有效的 ER-α 结合剂 ( IC 50 = 0.44 nM)。此外，21b和其他获得的硒类似物对大鼠成肌细胞（H9C2）没有毒性，表明取代的苯并[ b ]硒酚是开发用于治疗 ER+ 癌症的 ER-α 调节剂和下调剂的前瞻性支架。

  DOI：

  10.1039/d3nj01739g
• 作为产物：
  描述：

  4-氟苯乙炔 、 4-甲氧基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.57h， 生成 3-(4-fluorophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-ol
  参考文献：
  名称：

  通过与炔丙醇截获酮丁酮的催化克莱森重排：从自由基产生和转化酮丁胺的策略。

  摘要：

  通过自由基与金属催化剂的配位，已经建立了促进两个自由基交叉偶联的有效策略。该策略提供了显着的能力，可以利用含腈的偶氮烷烃的反应性，并且可以建立与含腈的偶氮烷烃和炔丙醇的新型级联反应。通过使用该反应，获得了一系列炔属和烯丙基酰胺，它们为进一步衍生化提供了通用平台。

  DOI：

  10.1021/acs.orglett.0c02306

文献信息

• Catalytic Claisen Rearrangement by Intercepting Ketenimines with Propargylic Alcohols: A Strategy to Generate and Transform Ketenimines from Radicals
  作者：Xuyang Yan、Hongchi Liu、Shenquan Wei、Hanmin Huang

  DOI：10.1021/acs.orglett.0c02306

  日期：2020.9.4

  An efficient strategy for facilitating the cross-coupling of two radicals has been established via the coordination of a radical with a metal catalyst. This strategy provides a remarkable ability to harness the reactivity of nitrile-containing azoalkanes and enables a novel cascade reaction with nitrile-containing azoalkanes and propargylic alcohols to be established. By using this reaction, a range

  通过自由基与金属催化剂的配位，已经建立了促进两个自由基交叉偶联的有效策略。该策略提供了显着的能力，可以利用含腈的偶氮烷烃的反应性，并且可以建立与含腈的偶氮烷烃和炔丙醇的新型级联反应。通过使用该反应，获得了一系列炔属和烯丙基酰胺，它们为进一步衍生化提供了通用平台。
• Design, Synthesis, and Structure−Activity Relationship Studies of 3,4,6-Triphenylpyran-2-ones as Selective Cyclooxygenase-2 Inhibitors
  作者：P. N. Praveen Rao、Md. Jashim Uddin、Edward E. Knaus

  DOI：10.1021/jm049939b

  日期：2004.7.1

  A group of regioisomeric 3,4,6-triphenylpyran-2-ones with a MeSO2 pharmacophore at the paraposition of either a C-3 phenyl or a C-4 phenyl substituent on the central six-membered pyran-2-one ring were prepared and evaluated in vitro for their abilities to inhibit the isozymes COX-1 and COX-2. Structure-activity relationship (SAR) data, acquired by substituent modification at the para-position of the C-6 phenyl ring attached to the central pyranone, showed that 6-(4-methoxyphenyl)-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-one (12e) was the most potent and selective COX-2 inhibitor (COX-2 IC50 = 0.02 muM; COX-1 IC50 > 100 muM) with a high COX-2 selectivity index (SI > 5000) relative to the reference drugs celecoxib (COX-2 IC50 = 0.07 muM; SI = 474) and rofecoxib (COX-2 IC50 = 0.50 muM; SI > 200). 6-(4-Methoxyphenyl)-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-one (12e) was a more potent oral antiinflammatory agent (ID50 = 5.6 mg/kg) than celecoxib (ID50 = 10.8 mg/kg) in a carrageenan-induced rat paw edema assay. In a 4% NaCl-induced abdominal constriction assay, a 5 mg/kg oral dose of 12e exhibited good analgesic activity at different time intervals producing 37.5 and 69% inhibition of writhing at 30 and 60 min, respectively. In contrast, the corresponding 6-(4-methoxyphenyl)-4-(4-methanesulfonylphenyl)-3-phenylpyran-2-one regiosiomer (12o) was a less potent and selective COX-2 inhibitor (COX-2 IC50 = 0.45 muM; SI = 70). A molecular modeling study for 12e indicated that the p-OMe substituent on the C-6 phenyl ring interacts with the COX-2 binding site amino acids Ile(345), Val(349), Leu(359), Leu(531), and Met(535) and that the OMe substituent may be responsible for proper orientation of the C-3 p-SO2Me-phenyl ring within the COX-2 secondary pocket (Gln(192), Arg(513), and Phe(518)). These results show that the COX-2 selectivity and potency of 3,4,6-triphenylpyranone regioisomers can be modulated by appropriate placement of the p-SO2Me pharmacophore on either the C-3 or C-4 phenyl moiety. In addition, electronic properties at the para-position of a C-6 phenyl substituent on the central pyranone ring govern COX-2 inhibitory potency and selectivity by controlling the orientation of the p-SO2Me pharmacophore within the COX-2 secondary pocket.
• Gold‐Catalyzed Regioselective Synthesis of Pyrazolo[1,4]oxazepines via Intramolecular <i>7</i> ‐ <i>endo‐dig</i> Cyclization
  作者：Yadagiri Thummala、Chittala Emmaniel Raju、Dalovai Purnachandar、Gottam Sreenivasulu、Venkata Ramana Doddi、Galla V. Karunakar

  DOI：10.1002/ejoc.201901852

  日期：2020.6.30

  An efficient gold‐catalyzed intramolecular regioselective synthesis of pyrazolo[1,4]oxazepines were developed from alkynyl‐substituted pyrazoles via 7‐endo dig cyclization. In this reaction a new C–N bond was formed and substituted pyrazolo[1,4]oxazepines were obtained in moderate to very good yields.

  通过炔基取代的吡唑经7-内位-挖-环化反应，开发了一种高效的金催化的吡唑并[1,4]氧杂氮杂物分子内区域选择性合成方法。在该反应中，形成了一个新的C–N键，并以中等至非常高的产率获得了取代的吡唑并[1,4]恶氮杂s。
• Selenium analogues of rintodestrant (G1T48) as potent estrogen receptor modulators and downregulators
  作者：Edgars Paegle、Pavels Dimitrijevs、Pavel Arsenyan

  DOI：10.1039/d3nj01739g

  日期：——

  against cancer. Nowadays, selective estrogen receptor modulators (SERMs) and downregulators (SERDs) are used as the first-line medical treatment for estrogen receptor positive (ER+) tumors. Herein we report the design and synthesis of 7 novel benzoselenophenes, and their ER-α binding activity and cytotoxicity. The TR-FRET competitive ER-α binding experiments have shown that (E)-3-(4-((6-hydroxy-2-(4-hyd

  靶向治疗是对抗癌症的现代方向之一。如今，选择性雌激素受体调节剂（SERM）和下调剂（SERD）被用作雌激素受体阳性（ER+）肿瘤的一线治疗方法。在此，我们报告了 7 种新型苯并硒吩的设计和合成，及其 ER-α 结合活性和细胞毒性。TR-FRET竞争性ER-α结合实验表明，( E )-3-(4-((6-羟基-2-(4-羟基苯甲酰基)苯并[ b ]硒酚-3-基)氧基)苯基)丙烯酸酸 ( 21b ) 是一种比广为人知的 SERM 药物雷洛昔芬 (IC 50 = 1.78 nM)更有效的 ER-α 结合剂 ( IC 50 = 0.44 nM)。此外，21b和其他获得的硒类似物对大鼠成肌细胞（H9C2）没有毒性，表明取代的苯并[ b ]硒酚是开发用于治疗 ER+ 癌症的 ER-α 调节剂和下调剂的前瞻性支架。