1-phenyl-3-(pyridin-3-yl)prop-2-yn-1-ol | 134161-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-phenyl-3-(pyridin-3-yl)prop-2-yn-1-ol
• 英文别名: 1-phenyl-3-pyridin-3-yl-prop-2-yn-1-ol；1-phenyl-3-(3-pyridyl)prop-2-yn-1-ol；α-[(3-pyridinyl)ethynyl]-benzenemethanol；alpha-[(3-Pyridinyl)ethynyl]-benzenemethanol；1-phenyl-3-pyridin-3-ylprop-2-yn-1-ol
• CAS: 134161-19-6
• 化学式: C₁₄H₁₁NO
• 分子量: 209.247
• InChiKey: KUVJLZSPQPYDSW-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±37.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(pyridin-3-yl)prop-2-yn-1-ol 在 manganese(IV) oxide 、 sodium hydride 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 3-(4-Methanesulfonyl-phenyl)-6-phenyl-4-pyridin-3-yl-pyran-2-one
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship Studies of 3,4,6-Triphenylpyran-2-ones as Selective Cyclooxygenase-2 Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm049939b
• 作为产物：
  描述：

  苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-phenyl-3-(pyridin-3-yl)prop-2-yn-1-ol
  参考文献：
  名称：

  NaH mediated isomerisation–allylation reaction of 1,3-substituted propenols

  摘要：

  建立了一种通过基础介导的异构化-烯丙基化协议来合成1,3-二取代丙烯醇的方法。报告中同时使用了二芳基和芳基-硅基底物以及取代的烯丙基溴。还进行了机理实验以阐明反应途径。

  DOI：

  10.1039/c3ob41857j

文献信息

• Sustainable Ligand‐Free Heterogeneous Palladium‐Catalyzed Sonogashira Cross‐Coupling Reaction in Deep Eutectic Solvents
  作者：Francesco Messa、Giuseppe Dilauro、Filippo M. Perna、Paola Vitale、Vito Capriati、Antonio Salomone

  DOI：10.1002/cctc.201902380

  日期：2020.4.6

  cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides were successfully coupled with both aromatic and aliphatic alkynes in yields ranging from 50 to 99 % within 3 h at 60 °C. The aforementioned catalytic system proved to be effective also towards

  发现在不存在外部配体的情况下，在环境友好的氯化胆碱/甘油共晶混合物中，市售和廉价的Pd / C可以促进Sonogashira偶联。在非均相条件下，在60°C下3小时内，（杂）芳基碘化物就成功地与芳烃和脂族炔烃偶合，收率范围为50％至99％。事实证明，上述催化体系对富电子碘化物也有效，众所周知，该碘化物在Pd催化的Sonogashira偶联反应中反应性差。共晶混合物和催化剂可以轻松，成功地循环使用多达4次，而E因子低至24.4。
• Base-Mediated Cascade Rearrangements of Aryl-Substituted Diallyl Ethers
  作者：Jolene P. Reid、Catherine A. McAdam、Adam J. S. Johnston、Matthew N. Grayson、Jonathan M. Goodman、Matthew J. Cook

  DOI：10.1021/jo502403n

  日期：2015.2.6

  Two base-mediated cascade rearrangement reactions of diallyl ethers were developed leading to selective [2,3]-Wittig–oxy-Cope and isomerization–Claisen rearrangements. Both diaryl and arylsilyl-substituted 1,3-substituted propenyl substrates were examined, and each exhibits unique reactivity and different reaction pathways. Detailed mechanistic and computational analysis was conducted, which demonstrated

  开发了两个碱基介导的二烯丙基醚的级联重排反应，从而导致选择性的[2,3] -Wittig-oxy-Cope和异构化-Claisen重排。对二芳基和芳基甲硅烷基取代的1,3-取代的丙烯基底物均进行了检测，每种底物均具有独特的反应性和不同的反应途径。进行了详细的机理和计算分析，表明碱和溶剂的作用是观察到的反应性和选择性的关键。交叉实验还表明，这些反应以一定程度的解离进行，并且机理途径是高度复杂的，具有多种竞争途径。
• 1-phenyl-3-aryl-2-propyne-1-one useful as calcium uptake inhibitors
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05223518A1

  公开（公告）日：1993-06-29

  This invention relates to 1-phenyl-3-aryl-2-propyne-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.

  这项发明涉及1-苯基-3-芳基-2-丙炔-1-酮，这些化合物在白细胞和血小板中作为钙摄取抑制剂的用途，以及含有这些化合物作为活性成分的药物组合物，以及它们的制备过程。
• Calcium uptake inhibitors
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05409942A1

  公开（公告）日：1995-04-25

  This invention relates to 1-phenyl-3-aryl-2-propyne-1-ones, the use of these compounds as calcium uptake inhibitors in leukocytes and thrombocytes, and pharmaceutical compositions containing these compounds as active ingredients, and the process of their preparation.

  本发明涉及1-苯基-3-芳基-2-丙炔-1-酮，这些化合物作为白细胞和血小板中钙离子摄取抑制剂的用途，以及含有这些化合物作为活性成分的制药组合物和它们的制备过程。
• Lanthanide-catalyzed deamidative cyclization of secondary amides and ynones through tandem C–H and C–N activation
  作者：Junxi Zhang、Yitu Wang、Xigeng Zhou

  DOI：10.1039/d3cc00216k

  日期：——

  We report a new cyclization reaction of amides with ynones via tandem amide α-C–H and C–N activation enabled by a non-redox rare earth catalyst.

  我们报道了一种新的环化反应，使用非氧化还原罕见土壤金属催化剂，通过串联酰胺α-C-H和C-N活化，使酰胺与炔酮发生环化反应。