1-(3-fluorophenyl)-1,3-propanediol | 51699-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-fluorophenyl)-1,3-propanediol
• 英文别名: 1-(m-Fluorphenyl)-propandiol-1,3；1-(3-Fluorophenyl)propane-1,3-diol
• CAS: 51699-47-9
• 化学式: C₉H₁₁FO₂
• 分子量: 170.184
• InChiKey: NNSRZZIDIQCCOS-UHFFFAOYSA-N

物化性质

• 沸点：
  314.3±27.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  1-(3-fluorophenyl)-1,3-propanediol 、 阿德福韦 在 吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 、
  参考文献：
  名称：

  Pradefovir: A Prodrug That Targets Adefovir to the Liver for the Treatment of Hepatitis B

  摘要：

  Adefovir dipivoxil, a marketed drug for the treatment of hepatitis B, is dosed at submaximally efficacious doses because of renal toxicity. In an effort to improve the therapeutic index of adefovir, 1-aryl-1,3-propanyl prodrugs were synthesized with the rationale that this selectively liver-activated prodrug class would enhance liver levels of the active metabolite adefovir diphosphate (ADV-DP) and/or decrease kidney exposure. The lead prodrug (14, MB06866, pradefovir), identified from a variety of in vitro and in vivo assays, exhibited good oral bioavailability (F = 42%, mesylate salt, rat) and rate of prodrug conversion to ADV-DP. Tissue distribution studies in the rat using radiolabeled materials showed that cyclic 1-aryl-1,3-propanyl prodrugs enhance the delivery of adefovir and its metabolites to the liver, with pradefovir exhibiting a 12-fold improvement in the liver/kidney ratio over adefovir dipivoxil.

  DOI：

  10.1021/jm7012216
• 作为产物：
  描述：

  3'-氟苯乙酮 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 甲醇 、 甲苯 、 mineral oil 为溶剂， 反应 11.0h， 生成 1-(3-fluorophenyl)-1,3-propanediol
  参考文献：
  名称：

  Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: the influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

  摘要：

  Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.06.004

文献信息

• Novel 2'-C-methyl nucleoside derivatives
  申请人：Reddy Raja K.

  公开号：US20050182252A1

  公开（公告）日：2005-08-18

  Compounds of Formula I, stereoisomers, and pharmaceutically acceptable salts or prodrugs thereof, their preparation, and their uses for the treatment of hepatitis C viral infection are described:

  化合物I的配方、立体异构体以及其药用可接受的盐或前药，它们的制备以及它们用于治疗丙型肝炎病毒感染的用途被描述：
• 4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamides as antiviral agents
  申请人：Schnute Edward Mark

  公开号：US20050004161A1

  公开（公告）日：2005-01-06

  The invention provides a compound of formula I: wherein A, B, R 1 , R 2 , R 3 , and R 4 are as defined in the specification. The compounds of the present invention are useful for treating viral infections, in particular a herpesviral infection.

  该发明提供了化合物I的结构，其中A、B、R1、R2、R3和R4如规范中定义。本发明的化合物对治疗病毒感染，特别是单纯疱疹病毒感染，具有实用价值。
• [EN] NOVEL CYCLIC PHOSPHATE DIESTERS OF 1,3-PROPANE-1-ARYL DIOLS AND THEIR USE IN PREPARING PRODRUGS<br/>[FR] NOUVEAUX DIESTERS PHOSPHORIQUES CYCLIQUES DE DIOLS DE 1,3-PROPANE-1-ARYLIQUES ET LEUR UTILISATION POUR LA PREPARATION DE PROMEDICAMENTS
  申请人：METABASIS THERAPEUTICS INC

  公开号：WO2004041834A2

  公开（公告）日：2004-05-21

  Compounds of Formula (I), their preparation and synthetic intermediates, and their use in the synthesis of prodrugs; wherein: V and L are trans relative to one another; V is selected from group consisting of carbocyclic aryl, substituted carbocyclic aryl, heteroaryl, and substituted heteroaryl; and L is a leaving group selected from the group consisting of halogen, alkyl sulfonate, aryloxy optionally substituted with 1-2 substituents, N-containing heteroaryl, and N-hydroxy-nitrogen containing heteroaryl; and salts thereof.

  公式（I）的化合物，其制备和合成中间体，以及它们在前药合成中的应用；其中：V和L相对于彼此是反式的；V选自群体，包括环烷基芳基，取代环烷基芳基，杂环芳基和取代杂环芳基；L是离去基，选自群体，包括卤素，烷基磺酸盐，取代1-2个取代基的芳氧基，含N的杂环芳基和含N-羟基-氮的杂环芳基；以及其盐。
• [EN] N-SUBSTITUTED TRICYCLIC 3-AMINOPYRAZOLES AS PDFG RECEPTOR INHIBITORS<br/>[FR] 3-AMINOPYRAZOLES TRICYCLIQUES N-SUBSTITUES COMME INHIBITEURS DES RECEPTEURS DU PDFG
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2003097609A1

  公开（公告）日：2003-11-27

  The invention is directed to N-substituted tricyclic 3-AMINOPYRAZOLE derivatives, which are useful as inhibitors of platelet-derived growth factor receptor (PDGF-R) kinase, and methods for the preparation of said derivatives. The present invention is further directed to pharmaceutical compositions comprising the compounds of the presentinvention and to methods for treating conditions such as tumors and other cell proliferative disorders.

  本发明涉及N-取代的三环3-氨基吡唑衍生物，其作为血小板源性生长因子受体（PDGF-R）激酶的抑制剂具有用途，以及制备该衍生物的方法。本发明还涉及包含本发明化合物的制药组合物，以及用于治疗肿瘤和其他细胞增殖性疾病的方法。
• Novel cyclic phosphate diesters of 1,3-propane-1-aryl diols and their use in preparing prodrugs
  申请人：——

  公开号：US20040192651A1

  公开（公告）日：2004-09-30

  Compounds of Formula I, their preparation and synthetic intermediates, and their use in the synthesis of prodrugs: 1 wherein: V and L are trans relative to one another; V is selected from group consisting of carbocyclic aryl, substituted carbocyclic aryl, heteroaryl, and substituted heteroaryl; and L is a leaving group selected from the group consisting of halogen, alkyl sulfonate, aryloxy optionally substituted with 1-2 substituents, N-containing heteroaryl, and N-hydroxy-nitrogen containing heteroaryl; and salts thereof.

  公式I的化合物，它们的制备和合成中间体，以及它们在前药合成中的应用： 其中： V和L是相对于彼此的反式； V选自群组，包括碳环芳基，取代的碳环芳基，杂环芳基和取代的杂环芳基； L是离去基，选自群组，包括卤素，烷基磺酸盐，取代1-2个取代基的芳氧基，含氮杂环和含N-羟基-氮杂环； 以及它们的盐。