2-hydroxy-5-fluorobenzylacetone | 1019769-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-hydroxy-5-fluorobenzylacetone
• 英文别名: 4-(5-fluoro-2-hydroxyphenyl)butan-2-one
• CAS: 1019769-63-1
• 化学式: C₁₀H₁₁FO₂
• 分子量: 182.195
• InChiKey: FSYMRCHOHTXOAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-5-fluorobenzylacetone 在 1,3-二溴-5,5-二甲基海因 、 (11bR)-4-((4-(tert-butyl)-2,6-dimethylphenyl)amino)-2,6-bis(triphenylsilyl)dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 15.5h， 生成 (R)-2-(bromomethyl)-6-fluoro-2-methylchromane
  参考文献：
  名称：

  手性酰胺磷酸盐催化剂和卤代路易斯酸诱导的对映选择性卤氧和卤氮杂环化

  摘要：

  2-烯基苯酚和烯酰胺的催化对映选择性卤环化已经通过使用手性酰胺磷酸盐催化剂和卤代路易斯酸实现。密度泛函理论计算表明催化剂的路易斯碱度在反应性和对映选择性中起重要作用。所得手性卤代色满可以在短时间内转化为 α-生育酚、α-生育三烯酚、代达林 A 和英格列酮。此外，具有不饱和侧链的卤化产物可在自由基环化条件下提供多环加合物。

  DOI：

  10.1021/jacs.8b02607
• 作为产物：
  描述：

  4-(5-氟-2-羟基苯基)丁-3-烯-2-酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 2-hydroxy-5-fluorobenzylacetone
  参考文献：
  名称：

  钯催化碳硼化合成硼化茚满

  摘要：

  σ-烷基-钯配合物在催化中的拦截是产生分子复杂性的有力策略。我们已经证明了用于合成硼化茚满的钯催化的碳硼化反应，该反应以良好的产率和适度的对映选择性进行。

  DOI：

  10.1002/ejoc.202100309

文献信息

• COMPOUNDS
  申请人：Boyle Jessica

  公开号：US20080161288A1

  公开（公告）日：2008-07-03

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are agonists at the beta-2 adrenoceptor. They are useful as feed additives for livestock animals.

  化学式为（I）的化合物及其药学上可接受的盐是β-2肾上腺素受体激动剂。它们可用作家畜饲料添加剂。
• WO2008/44127
  申请人：——

  公开号：——

  公开（公告）日：——
• Identification of Michael Acceptor-Centric Pharmacophores with Substituents That Yield Strong Thioredoxin Reductase Inhibitory Character Correlated to Antiproliferative Activity
  作者：Fei-Fei Gan、Kamila K. Kaminska、Hong Yang、Chin-Yee Liew、Pay-Chin Leow、Choon-Leng So、Lan N.L. Tu、Amrita Roy、Chun-Wei Yap、Tse-Siang Kang、Wai-Keung Chui、Eng-Hui Chew

  DOI：10.1089/ars.2012.4909

  日期：2013.10.10

  Aims: The role of thioredoxin reductase (TrxR) in tumorigenesis has made it an attractive anticancer target. A systematic approach for development of novel compounds as TrxR inhibitors is currently lacking. Structurally diversified TrxR inhibitors share in common electrophilic propensities for the sulfhydryl groups, among which include the Michael reaction acceptors containing an ,-unsaturated carbonyl moiety. We aimed to identify features among structurally diversified Michael acceptor-based compounds that would yield a strong TrxR inhibitory character. Results: Structurally dissimilar Michael acceptor-based natural compounds such as isobutylamides, zerumbone, and shogaols (SGs) were found to possess a poor TrxR inhibitory activity, indicating that a sole Michael acceptor moiety was insufficient to produce TrxR inhibition. The 1,7-diphenyl-hept-3-en-5-one pharmacophore in 3-phenyl-3-SG, a novel SG analog that possessed comparable TrxR inhibitory and antiproliferative potencies as 6-SG, was modified to yield 1,5-diphenyl-pent-1-en-3-one (DPPen) and 1,3-diphenyl-pro-1-en-3-one (DPPro, also known as chalcone) pharmacophores. These Michael acceptor-centric pharmacophores, when substituted with the hydroxyl and fluorine groups, gave rise to analogs displaying a TrxR inhibitory character positively correlated to their antiproliferative potencies. Lead analogs 2,2-diOH-5,5-diF-DPPen and 2-OH-5-F-DPPro yielded a half-maximal TrxR inhibitory concentration of 9.1 and 10.5M, respectively, after 1-h incubation with recombinant rat TrxR, with the C-terminal selenocysteine residue found to be targeted. Innovation: Identification of Michael acceptor-centric pharmacophores among diversified compounds demonstrates that a systematic approach to discover and develop Michael acceptor-based TrxR inhibitors is feasible. Conclusion: A strong TrxR inhibitory character correlated to the antiproliferative potency is attributed to structural features that include an ,-unsaturated carbonyl moiety centered in a DPPen or DPPro pharmacophore bearing hydroxyl and fluorine substitutions. Antioxid. Redox Signal. 19, 1149-1165.
• HETEROCYCLIC COMPOUNDS USEFUL AS ANABOLIC AGENTS FOR LIVESTOCK ANIMALS
  申请人：Pfizer Limited

  公开号：EP2079747A1

  公开（公告）日：2009-07-22
• [EN] HETEROCYCLIC COMPOUNDS USEFUL AS ANABOLIC AGENTS FOR LIVESTOCK ANIMALS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES UTILES EN TANT QU'AGENTS ANABOLIQUES POUR LE BÉTAIL
  申请人：PFIZER LTD

  公开号：WO2008044127A1

  公开（公告）日：2008-04-17

  [EN] Compounds of formula (I) and pharmaceutically acceptable salts thereof are agonists at the beta-2 adrenoceptor. They are useful as feed additives for livestock animals.
  [FR] Les composés représentés par la formule (I) et les sels de ceux-ci acceptables du point de vue pharmaceutique sont des agonistes du récepteur bêta 2 adrénergique. Ils sont utiles en tant qu'additifs alimentaires pour le bétail.