1-(2-chlorophenyl)-1,3-propanediol | 705969-10-4

• 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-chlorophenyl)-1,3-propanediol
• 英文别名: 1-(2-chlorophenyl)propane-1,3-diol
• CAS: 705969-10-4
• 化学式: C₉H₁₁ClO₂
• 分子量: 186.638
• InChiKey: FZDSULCYDIFJPE-UHFFFAOYSA-N

物化性质

• 沸点：
  345.3±27.0 °C(Predicted)
• 密度：
  1.274±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-chlorophenyl)-1,3-propanediol 在 盐酸 、 叔丁基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 5-amino-2-((4-(2-chlorophenyl)-2-oxido-1,3,2-dioxaphosphinan-2-yl)oxy)benzoic acid
  参考文献：
  名称：

  设计，合成和评价新型5-氨基水杨酸环状磷酸酯作为细胞色素P450活化的前药。

  摘要：

  设计并合成了四种新型消炎药5-氨基水杨酸（5-ASA）的环状磷酸酯，作为细胞色素P450（CYP）活化的前药。这些前药可用于靶向肠壁，因为已知这些类型的环状磷酸盐主要被CYP3A形式激活，CYP3A形式不仅在肝脏中表达，而且在小肠中表达，并且在结肠中表达程度较低。本研究表明，芳香族环活化取代基（如氯）绝对是获得5-ASA环状磷酸酯前药所需的酶促裂解所必需的。但是，活化取代基的位置也对化学稳定性有很大的影响，因此，

  DOI：

  10.1021/mp300330v
• 作为产物：
  描述：

  (+)-3-hydroxy-3-(2-chlorophenyl)propionic acid ethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1-(2-chlorophenyl)-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

• Tandem Catalysis by Lipase in a Vinyl Acetate-Mediated Cross-Aldol Reaction
  作者：Manjeet Kumar、Bhahwal A. Shah、Subhash C. Taneja

  DOI：10.1002/adsc.201000980

  日期：2011.5

  The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate‐mediated aldol reaction. The reaction was facilitated through the lipase‐catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal

  脂肪酶Novozym435（0.6％w / w）与乙酸乙烯酯/异丙烯基乙酸酯介导的醛醇缩合反应中的有机催化剂一起使用。该反应通过脂肪酶催化的乙醛/丙酮原位生成而得以促进。本方法的重要特征包括温和且容易的反应条件，脂肪酶的可再生性，相对高的收率和最小的副产物形成。
• 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：
• [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。
• Non-nucleoside reverse transcriptase inhibitors
  申请人：Simoneau Bruno

  公开号：US20050054639A1

  公开（公告）日：2005-03-10

  Disclosed herein are compounds of formula Ar 1 —X—W—Ar 2 wherein Ar 1 and Ar 2 represent aryl groups characterized generally as aromatic heterocycles (e.g. imidazolyl or tetrazolyl) or carbocycles (e.g. phenyl or naphthalenyl); the aryl groups are optionally substituted or fused with other heterocycles or carbocycles; the aryl groups can bear substituents such as alkyl, halo or O-alkyl. X is a heteroatom, a valence bond or an optionally substituted divalent methylene, and W represents a spacer; typical spacers include divalent alkylene or alkylene-amido, -amido or -oxy radicals, which may optionally be substituted (e.g. hydroxyl or oxo). A typical compound is a derivative of 2-(N-napthalenyltetrazolylthio)-N-(2-nitrophenyl)acetamide. The compounds have inhibitory activity against Wild Type and single or double mutant strains of HIV.

  本文披露了公式Ar1-X-W-Ar2的化合物，其中Ar1和Ar2代表芳基基团，通常为芳香杂环（例如咪唑基或四唑基）或碳环（例如苯基或萘基），芳基基团可以选择性地与其他杂环或碳环取代或融合，芳基基团可以带有烷基，卤素或O-烷基等取代基。X是杂原子，价键或选择性取代的二价亚甲基，W代表间隔物；典型的间隔物包括二价烷基或烷基酰胺，-酰胺或-氧基基团，这些基团可以选择性地取代（例如羟基或氧代基）。典型的化合物是2-（N-萘基四唑基硫基）-N-（2-硝基苯基）乙酰胺的衍生物。这些化合物对HIV的野生型和单个或双重突变株具有抑制活性。
• 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。