1-(4-aminopiperidin-1-yl)-3-(3,4-difluorophenoxy)propan-2-ol | 188174-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-aminopiperidin-1-yl)-3-(3,4-difluorophenoxy)propan-2-ol
• CAS: 188174-28-9
• 化学式: C₁₄H₂₀F₂N₂O₂
• 分子量: 286.322
• InChiKey: CGPRCMFSIKVGSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-氯苯并噻唑 、 1-(4-aminopiperidin-1-yl)-3-(3,4-difluorophenoxy)propan-2-ol 以 水 为溶剂， 反应 10.0h， 以91%的产率得到1-(4-(benzothiazol-2-ylamino)piperidin-1-yl)-3-(3,4-difluorophenoxy)propan-2-ol
  参考文献：
  名称：

  Protecting group-Free Concise Synthesis of (RS)/(S)-Lubeluzole

  摘要：

  Three new, concise, and protecting group-free synthetic routes for (RS)- and (S)-lubeluzole are reported in higher (46-62%) overall yields compared to the reported procedures (6-35%). The key steps involve C-N bond formation via epoxide aminolysis and nucleophilic substitution of 2-chlorobenzothiazole with suitably designed precursor amines and are performed in aqueous medium. Water offers an advantage in promoting the reactions compared to organic solvents and its role Is envisaged as hydrogen-bond mediated electrophile-nucleophile dual activation.

  DOI：

  10.1021/ol302601b
• 作为产物：
  描述：

  3,4-二氟苯酚 在 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 16.0h， 生成 1-(4-aminopiperidin-1-yl)-3-(3,4-difluorophenoxy)propan-2-ol
  参考文献：
  名称：

  Protecting group-Free Concise Synthesis of (RS)/(S)-Lubeluzole

  摘要：

  Three new, concise, and protecting group-free synthetic routes for (RS)- and (S)-lubeluzole are reported in higher (46-62%) overall yields compared to the reported procedures (6-35%). The key steps involve C-N bond formation via epoxide aminolysis and nucleophilic substitution of 2-chlorobenzothiazole with suitably designed precursor amines and are performed in aqueous medium. Water offers an advantage in promoting the reactions compared to organic solvents and its role Is envisaged as hydrogen-bond mediated electrophile-nucleophile dual activation.

  DOI：

  10.1021/ol302601b

文献信息

• COMPOSES HETEROCYCLIQUES POUR LE TRAITEMENT DE L'ISCHEMIE MYOCARDIQUE
  申请人：PIERRE FABRE MEDICAMENT

  公开号：EP0842174A1

  公开（公告）日：1998-05-20
• US6011032A
  申请人：——

  公开号：US6011032A

  公开（公告）日：2000-01-04
• [EN] HETEROCYCLIC COMPOUNDS FOR TREATING MYOCARDIAL ISCHAEMIA<br/>[FR] COMPOSES HETEROCYCLIQUES POUR LE TRAITEMENT DE L'ISCHEMIE MYOCARDIQUE
  申请人：PIERRE FABRE MEDICAMENT

  公开号：WO1997005134A1

  公开（公告）日：1997-02-13

  (EN) Novel substituted N-heterocyclyl-1-aryloxyalkyl-4-piperidineamines of formula (I), wherein each of R1 to R4, which are the same or different, is hydrogen, optionally branched C1-4 alkyl, optionally branched C1-4 alkyloxy, a halo grouping, a nitro grouping, a hydroxy grouping or a trifluoromethyl or trifluoromethoxyl grouping; R5 is hydrogen, optionally branched C1-6 alkyl, optionally branched C7-12 phenylalkyl optionally substituted on the aromatic by one or more radicals having the same definition as R1; W and X are oxygen or sulphur; Y is a C2-6 polymethylene grouping or a radical -CH2-CH(OH)-CH2-; and n is 0 or 1, are disclosed. Pure R or S isomers of said compounds, where applicable, as well as mixtures thereof, are also disclosed. Furthermore, therapeutically acceptable organic or inorganic salts of the compounds of general formula (I), and any hydrates thereof, are disclosed. Finally, a method for preparing the claimed compounds, and their use as drugs, are disclosed.(FR) L'invention concerne de nouvelles N-hétérocyclyl-1-aryloxyalcoyl-4-pipéridinamines substituées de formule (I), dans laquelle R1 à R4 égaux ou différents représentent: un hydrogène; un alcoyle ramifié ou non renfermant de 1 à 4 atomes de carbone; un alcoyloxy ramifié ou non renfermant de 1 à 4 atomes de carbone; un groupement halogéno; un groupement nitro; un groupement hydroxy; un groupement trifluorométhyle ou trifluorométhoxyle. R5 représente: un hydrogène; un alcoyle ramifié ou non renfermant de 1 à 6 atomes de carbone; un phénylalcoyle ramifié ou non renfermant de 7 à 12 carbones, pouvant être substitué sur l'aromatique par un ou deux radicaux définis comme R1. W et X représentent: un oxygène ou un soufre. Y représente: un groupement polyméthylénique renfermant de 2 à 6 atomes de carbone; le radical -CH2-CH(OH)-CH2-; n peut prendre les valeurs 0 ou 1. L'invention concerne aussi bien - lorsqu'ils existent - les isomères R ou S purs que leurs mélanges. La présente invention inclut les sels minéraux ou organiques thérapeutiquement acceptables des composés de formule générale (I) et leurs hydrates éventuels. L'invention concerne aussi le procédé de préparation des composés revendiqués ainsi que leur application comme médicaments.
• Protecting group-Free Concise Synthesis of (<i>RS</i>)/(<i>S</i>)-Lubeluzole
  作者：Damodara N. Kommi、Dinesh Kumar、Kapileswar Seth、Asit K. Chakraborti

  DOI：10.1021/ol302601b

  日期：2013.3.15

  Three new, concise, and protecting group-free synthetic routes for (RS)- and (S)-lubeluzole are reported in higher (46-62%) overall yields compared to the reported procedures (6-35%). The key steps involve C-N bond formation via epoxide aminolysis and nucleophilic substitution of 2-chlorobenzothiazole with suitably designed precursor amines and are performed in aqueous medium. Water offers an advantage in promoting the reactions compared to organic solvents and its role Is envisaged as hydrogen-bond mediated electrophile-nucleophile dual activation.