3-(6-氟-2-吡啶基)-1-丙醇 | 162854-31-1

• 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
• 中文名称: 3-(6-氟-2-吡啶基)-1-丙醇
• 英文名称: 6-fluoro-2-pyridinepropanol
• 英文别名: 2-fluoro-6-(3-hydroxypropyl)pyridine；3-(6-fluoropyridin-2-yl)propan-1-ol
• CAS: 162854-31-1
• 化学式: C₈H₁₀FNO
• mdl: MFCD18802455
• 分子量: 155.172
• InChiKey: MEZSCAOKTAWLCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<3-(5-methyl-1,2,4-oxadiazolyl)>-2,6-dimethylphenol 、 3-(6-氟-2-吡啶基)-1-丙醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以55%的产率得到2-fluoro-6-<3-<4-<3-(5-methyl-1,2,4-oxadiazolyl)>-2,6-dimethylphenoxy>propyl>pyridine
  参考文献：
  名称：

  Picornavirus Inhibitors: Trifluoromethyl Substitution Provides a Global Protective Effect against Hepatic Metabolism

  摘要：

  Several modifications of the oxazoline ring of WIN 54954, a broad spectrum antipicornavirus compound, have been prepared in order to address the acid lability and metabolic instability of this compound. We have previously shown that the oxadiazole analogue 3 displayed comparable activity against a variety of rhinoviruses and appeared to be stable to acid. A monkey liver microsomal assay was developed to examine the metabolic stability in vitro of both compounds, and it was determined that WIN 54954 displayed 18 metabolic products while 3 was converted to 8 products. Two major products of 3 were determined by LC-MS/MS to be monohydroxylated at each of the terminal methyl groups. Replacement of the methyl on the isoxazole ring with a trifluoromethyl group, while preventing hydroxylation at this position, did not reduce the sensitivity of the molecule to microsomal metabolism at other sites. However, the (trifluoromethyl)oxadiazole 9 not only prevented hydroxylation at this position but also provided protection at the isoxazole end of the molecule, resulting in only two minor products to the extent of 4%. The major product was identified as the monohydroxylated compound 23. The global metabolic protective effect of trifluoromethyl group on the oxadiazole ring was further demonstrated by examining a variety of analogues including heterocyclic replacements of the isoxazole ring. In each case, the trifluoromethyl analogue displayed a protective effect when compared to the corresponding methyl analogue.

  DOI：

  10.1021/jm00008a014
• 作为产物：
  描述：

  环氧乙烷 、 2-氟-6-甲基吡啶 在 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以1.3 g (30.9%)的产率得到3-(6-氟-2-吡啶基)-1-丙醇
  参考文献：
  名称：

  Therapeutic phenoxyalkylheterocycles

  摘要：

  式##STR1##中的化合物，其中Q选择自吡啶基、吡唑基、嘧啶基、喹啉基、吲哚基和7-吡啶基中的一种或这些基中的一种或两种取代基; Y是3-9个碳原子的烷基桥; R.sub.1和R.sub.2分别独立地选择自氢、卤素、烷基、烯基、氨基、烷硫基、羟基、羟基烷基、烷氧基烷基、烷硫基烷基、烷基磺基烷基、烷氧基、硝基、羧基、烷氧羰基、二烷基氨基烷基、烷基氨基烷基、氨基烷基、二氟甲基、三氟甲基或氰基; R.sub.3是烷氧羰基、烷基四唑基、取代或未取代的苯基或杂环基，其N-氧化物，或其药用可接受的酸盐是一种有效的抗小肠病毒药剂。

  公开号：

  US05618821A1

文献信息

• US5618821A
  申请人：——

  公开号：US5618821A

  公开（公告）日：1997-04-08
• US5763461A
  申请人：——

  公开号：US5763461A

  公开（公告）日：1998-06-09
• [EN] THERAPEUTIC PHENOXYALKYLHETEROCYCLES<br/>[FR] COMPOSES HETEROCYCLIQUES PHENOXYALKYLES THERAPEUTIQUES
  申请人：SANOFI WINTHROP, INC.

  公开号：WO1995031438A1

  公开（公告）日：1995-11-23

  (EN) Compounds of formula (I) wherein Pyr is chosen from the group consisting of pyridyl, pyrazyl, pyrimidyl, quinolyl, indolyl and 7-azaindolyl or any of these substituted with one or two substitutents chosen from alkyl, alkoxy, hydroxy, halo, cyano, nitro, hydroxyalkyl, alkoxyalkyl, alkanoyl, fluoroalkyl or the N-oxide of any of these, and Y is an alkylene bridge of 3-9 carbon atoms.(FR) L'invention concerne des composés de la formule (I), dans laquelle Pyr est choisi dans le groupe comprenant pyridyle, pyrazyle, pyrimidyle, quinolyle, indolyle et 7-azaindolyle, pouvant comporter un ou deux substituants choisis parmi alkyle, alcoxy, hydroxy, halo, cyano, nitro, hydroxyalkyle, alcoxyalkyle, alcanoyle, fluoroalkyle, ou l'oxide d'azote de chacun de ceux-ci, et Y représente un pont alkylène comprenant 3 à 9 atomes de carbone.
• Picornavirus Inhibitors: Trifluoromethyl Substitution Provides a Global Protective Effect against Hepatic Metabolism
  作者：Guy D. Diana、Patrick Rudewicz、Daniel C. Pevear、Theodore J. Nitz、Suzanne C. Aldous、David J. Aldous、David T. Robinson、Tandy Draper、Frank J. Dutko、Christopher Aldi、Guy Gendron、R. Christopher Oglesby、Deborah L. Volkots、Michael Reuman、Thomas R. Bailey、Richard Czerniak、Tracey Block、Robert Roland、James Oppermann

  DOI：10.1021/jm00008a014

  日期：1995.4.1

  Several modifications of the oxazoline ring of WIN 54954, a broad spectrum antipicornavirus compound, have been prepared in order to address the acid lability and metabolic instability of this compound. We have previously shown that the oxadiazole analogue 3 displayed comparable activity against a variety of rhinoviruses and appeared to be stable to acid. A monkey liver microsomal assay was developed to examine the metabolic stability in vitro of both compounds, and it was determined that WIN 54954 displayed 18 metabolic products while 3 was converted to 8 products. Two major products of 3 were determined by LC-MS/MS to be monohydroxylated at each of the terminal methyl groups. Replacement of the methyl on the isoxazole ring with a trifluoromethyl group, while preventing hydroxylation at this position, did not reduce the sensitivity of the molecule to microsomal metabolism at other sites. However, the (trifluoromethyl)oxadiazole 9 not only prevented hydroxylation at this position but also provided protection at the isoxazole end of the molecule, resulting in only two minor products to the extent of 4%. The major product was identified as the monohydroxylated compound 23. The global metabolic protective effect of trifluoromethyl group on the oxadiazole ring was further demonstrated by examining a variety of analogues including heterocyclic replacements of the isoxazole ring. In each case, the trifluoromethyl analogue displayed a protective effect when compared to the corresponding methyl analogue.
• Therapeutic phenoxyalkylheterocycles
  申请人：Sanofi, S.A.

  公开号：US05618821A1

  公开（公告）日：1997-04-08

  Compounds of the formula ##STR1## wherein Q is chosen from the group consisting of pyridyl, pyrazyl, pyrimidyl, quinolyl, indolyl and 7-azaindolyl or any of these substituted with one or two substituents; Y is an alkylene bridge of 3-9 carbon atoms; R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl or cyano; R.sub.3 is alkoxycarbonyl, alkyltetrazolyl, substituted or unsubstituted phenyl or heterocyclyl, the N-oxide thereof, or a pharmaceutically acceptable acid addition salt thereof is an effective antipicornaviral agent.

  式##STR1##中的化合物，其中Q选择自吡啶基、吡唑基、嘧啶基、喹啉基、吲哚基和7-吡啶基中的一种或这些基中的一种或两种取代基; Y是3-9个碳原子的烷基桥; R.sub.1和R.sub.2分别独立地选择自氢、卤素、烷基、烯基、氨基、烷硫基、羟基、羟基烷基、烷氧基烷基、烷硫基烷基、烷基磺基烷基、烷氧基、硝基、羧基、烷氧羰基、二烷基氨基烷基、烷基氨基烷基、氨基烷基、二氟甲基、三氟甲基或氰基; R.sub.3是烷氧羰基、烷基四唑基、取代或未取代的苯基或杂环基，其N-氧化物，或其药用可接受的酸盐是一种有效的抗小肠病毒药剂。