1-(2-bromophenyl)-1,3-propanediol | 862187-97-1

• 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-(2-bromophenyl)-1,3-propanediol
• 英文别名: 1-(2-Bromophenyl)propane-1,3-diol
• CAS: 862187-97-1
• 化学式: C₉H₁₁BrO₂
• 分子量: 231.089
• InChiKey: GMDZXLGJGQLAGC-UHFFFAOYSA-N

物化性质

• 沸点：
  366.3±27.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-bromophenyl)-1,3-propanediol 在 2-羟基-4-硝基吡啶 、 silver(I) acetate 、 palladium diacetate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 methyl 4'-bromo-3'-(2-(2-cyanophenyl)-1,3-dioxan-4-yl)-[1,1'-biphenyl]-2-carboxylate
  参考文献：
  名称：

  使用易于折叠的导向基团进行芳烃束缚二醇的区域选择性烯化和芳基化

  摘要：

  芳烃束缚的二醇构成了一类有价值的药物和生物活性天然产物分子的结构基序。在这项研究中，使用易于折叠的缩醛结构来连接吡啶和腈导向基团，开发了芳烃束缚的1,2-二醇和1,3-二醇的烯化和芳基化的区域选择性方案。该方法克服了短链二醇的空间位阻效应，得到了高产率和区域选择性的产物。这种高效的级联催化已成功用于天然产物的合成，例如前胡醇、紫花苜蓿和marmesin。

  DOI：

  10.1021/acs.orglett.4c00096
• 作为产物：
  描述：

  ethyl 3-(2-bromophenyl)-3-hydroxypropanoate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-(2-bromophenyl)-1,3-propanediol
  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

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：
• Process for preparation of cyclic prodrugs of PMEA and PMPA
  申请人：——

  公开号：US20030225277A1

  公开（公告）日：2003-12-04

  The method of preparing compounds of Formula I is described: 1 wherein: M and V are cis to one another and MPO 3 H 2 is a phosphonic acid selected from the group consisting of 9-(2-phosphonylmethoxyethyl)adenine, and (R)-9-(2-phosphonylmethoxypropyl)adenine; wherein V is phenyl, optionally substituted with 1-2 substituents selected from a group consisting of fluoro, chloro, and bromo; comprising: coupling a chiral 1-phenylpropane-1,3-diol, wherein the phenyl may be optionally substituted, with MPOCl 2 or an N-6 substituted analogue thereof. Additionally, methods and salt forms are described that enable isolation and purification of the desired isomer.

  描述了制备化合物I的方法：其中：M和V相互顺式，MPO3H2是从9-(2-磷酸甲氧基乙基)腺嘌呤和(R)-9-(2-磷酸甲氧基丙基)腺嘌呤组成的磷酸；其中V是苯基，可选地取代1-2个从氟、氯和溴组成的取代基；包括：将手性1-苯基丙烷-1,3-二醇（其中苯基可选地取代）与MPOCl2或其N-6取代类似物偶联。此外，还描述了使所需异构体隔离和纯化的方法和盐形式。
• [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。
• 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。
• PROCESS FOR PREPARATION OF CYCLIC PRODRUGS OF PMEA AND PMPA
  申请人：Metabasis Therapeutics, Inc.

  公开号：EP1504014B1

  公开（公告）日：2015-12-02