2-(5-fluoro-2-methoxyphenyl)-2-hydroxy-N,N-dimethylethanethioamide | 476198-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(5-fluoro-2-methoxyphenyl)-2-hydroxy-N,N-dimethylethanethioamide
• CAS: 476198-99-9
• 化学式: C₁₁H₁₄FNO₂S
• 分子量: 243.302
• InChiKey: JWYMMYAUFZBWDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5-fluoro-2-methoxyphenyl)-2-hydroxy-N,N-dimethylethanethioamide 在 盐酸 、 sodium hydroxide 、 四磷十氧化物 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 7-fluoro-4-methoxy-1-benzothiophene
  参考文献：
  名称：

  [EN] 3-ARYLOXY/THIO-3-SUBSTITUTED PROPANAMINES AND THEIR USE IN INHIBITING SEROTONIN AND NOREPHINEPHRINE REUPTAKE
  [FR] COMPOSES PHARMACEUTIQUES

  摘要：

  提供一种具有以下结构的化合物（I）：其中A从-O-和-S-中选择；X从C2-C8烷基，C2-C8烯基，C3-C8环烷基和C4-C8环烷基烷基中选择，每种基团可能分别被选自卤素，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S(O)n-（其中n为0，1或2），-CF3，-CN和-CONH2的最多3个取代基所取代；Y从苯基，萘基，二氢苯并噻吩基，苯并噻唑基，苯并异噻唑基，喹啉基，异喹啉基，萘啉基，噻吩吡啉基，茚基，1,3-苯并二氧杂环戊基，苯并噻吩基，吲哚基和苯并呋喃基中选择，每种基团可能分别被选自卤素，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S(O)n-（其中n为0，1或2），硝基，乙酰基，-CF3，-SCF3和氰基的最多4个或在可能的情况下5个取代基所取代；当Y为吲哚基时，它可以被选自C1-C4烷基的N-取代基取代或进一步取代；Z从H，OR3或F中选择，其中R3从H，C1-C6烷基和苯基C1-C6烷基中选择；R1和R2分别独立地为H或C1-C4烷基；但是，当Z为H时，Y可能不是可选择地取代的苯基或可选择地取代的萘基。

  公开号：

  WO2004043904A1
• 作为产物：
  描述：

  N,N-二甲基硫代甲酰胺 、 5-氟-2-甲氧基苯甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 1.0h， 以28%的产率得到2-(5-fluoro-2-methoxyphenyl)-2-hydroxy-N,N-dimethylethanethioamide
  参考文献：
  名称：

  [EN] 3-ARYLOXY/THIO-3-SUBSTITUTED PROPANAMINES AND THEIR USE IN INHIBITING SEROTONIN AND NOREPHINEPHRINE REUPTAKE
  [FR] COMPOSES PHARMACEUTIQUES

  摘要：

  提供一种具有以下结构的化合物（I）：其中A从-O-和-S-中选择；X从C2-C8烷基，C2-C8烯基，C3-C8环烷基和C4-C8环烷基烷基中选择，每种基团可能分别被选自卤素，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S(O)n-（其中n为0，1或2），-CF3，-CN和-CONH2的最多3个取代基所取代；Y从苯基，萘基，二氢苯并噻吩基，苯并噻唑基，苯并异噻唑基，喹啉基，异喹啉基，萘啉基，噻吩吡啉基，茚基，1,3-苯并二氧杂环戊基，苯并噻吩基，吲哚基和苯并呋喃基中选择，每种基团可能分别被选自卤素，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S(O)n-（其中n为0，1或2），硝基，乙酰基，-CF3，-SCF3和氰基的最多4个或在可能的情况下5个取代基所取代；当Y为吲哚基时，它可以被选自C1-C4烷基的N-取代基取代或进一步取代；Z从H，OR3或F中选择，其中R3从H，C1-C6烷基和苯基C1-C6烷基中选择；R1和R2分别独立地为H或C1-C4烷基；但是，当Z为H时，Y可能不是可选择地取代的苯基或可选择地取代的萘基。

  公开号：

  WO2004043904A1

文献信息

• [EN] 3-ARYLOXY/ THIO-2, 3-SUBSTITUTED PROPANAMINES AND THEIR USE IN INHIBITING SEROTONIN AND NOREPINEPHRINE REUPTAKE<br/>[FR] 3-ARYLOXY/THIO-2, 3-SUBSTITUE PROPANAMINES ET LEUR UTILISATION POUR INHIBER LE RECAPTAGE DE LA SEROTONINE ET DE LA NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2004043903A1

  公开（公告）日：2004-05-27

  There is provided a compound of formula (I) wherein A is selected from -O- and -S-; X is selected from phenyl optionally substituted with up to 5 substituents each independently selected from halo, C1-C4 alkyl and C1-C4 alkoxy, thienyl optionally substituted with up to 3 substituents each independently selected from halo and C1-C4 alkyl, and C2-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl and C4-C8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, -CF3, -CN and -CONH2; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3-benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, up to 5 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n- where n is 0, 1 or 2, nitro, acetyl, -CF3, -SCF3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; Z is selected from OR3 or F, wherein R3 is selected from H, C1-C6 alkyl and phenyl C1-C6 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereofwith the proviso that when Y is optionally substituted phenyl or optionally substituted 1,3-benzodioxolyl and Z is OR3 and X is optionally substituted phenyl then A is -S-.

  提供一种化合物，其化学式为（I），其中A从-O-和-S-中选择；X从苯基选项地取代，每个取代基可独立地从卤素、C1-C4烷基和C1-C4烷氧基中选择最多5个取代基，噻吩基选项地取代，每个取代基可独立地从卤素和C1-C4烷基中选择最多3个取代基，以及C2-C8烷基、C2-C8烯基、C3-C8环烷基和C4-C8环烷基烷基，每个基可选地取代，每个取代基可独立地从卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷基-S(O)n-（其中n为0、1或2）、-CF3、-CN和-CONH2中选择；Y从苯基、萘基、二氢苯并噻吩基、苯并噻唑基、苯并异噻唑基、喹啉基、异喹啉基、萘啉基、噻吩吡啉基、茚基、1,3-苯并二氧杂环戊基、苯并噻吩基、吲哚基和苯并呋喃基中选择，每个基可选地取代，最多可独立地从卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷基-S(O)n-（其中n为0、1或2）、硝基、乙酰基、- 、-S 和氰基中选择最多4个或在可能的情况下最多5个取代基；当Y为吲哚基时，它可以被取代或进一步被N-取代基取代，N-取代基从C1-C4烷基中选择；Z从OR3或F中选择，其中R3从H、C1-C6烷基和苯基C1-C6烷基中选择；R1和R2各自独立地为H或C1-C4烷基；以及其药学上可接受的盐，但有一个条件，即当Y为可选地取代的苯基或可选地取代的1,3-苯并二氧杂环戊基，Z为OR3且X为可选地取代的苯基时，A为-S-。
• [EN] HETEROARYLOXY 3-SUBSTITUTED PROPANAMINES S SEROTONIN AND NOREPINEPHRINE REUPTAKE INHIBITORS<br/>[FR] PROPANAMINES SUBSTITUEES EN 3 PAR UN HETEROARYLOXY UTILISEES EN TANT QU'INHIBITEURS DE RECAPTAGE DE SEROTONINE ET DE NOREPINEPHRINE
  申请人：LILLY CO ELI

  公开号：WO2002094262A1

  公开（公告）日：2002-11-28

  There is provided a heretoaryloxy 3-substituted propanamine compound of formula (I): wherein A is selected from -O- and -S-; X is selected from phenyl optionally substituted with up to 5 substituents selected from halo, C1-C4 alkyl and C1-C4 alkoxy, and thienyl optionally substituted with up to 3 substituents selected from halo and C1-C4 alkyl; Y is selected from benzothienyl, indolyl and benzofuranyl, optionally substituted with up to 5 substituents selected from halo, C1-C4 alkyl, C1-C4 alkoxy, nitro, acetyl and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof.

  提供了一种公式（I）的取代了3-丙胺基的芳氧基化化合物，其中A选自-O-和-S-; X选自苯基，可选地取代高达5个卤素、C1-C4烷基和C1-C4烷氧基，以及噻吩基，可选地取代高达3个卤素和C1-C4烷基; Y选自苯并噻吩基、吲哚基和苯并呋喃基，可选地取代高达5个卤素、C1-C4烷基、C1-C4烷氧基、硝基、乙酰基和氰基; 当Y为吲哚基时，它可以被C1-C4烷基的N取代或进一步取代; R1和R2各自独立地为H或C1-C4烷基;以及其药学上可接受的盐。
• 3-Aryloxy/thio-3-substituted propanamines and their use in inhibiting serotonin and norephinephrine reuptake
  申请人：Boulet Louis Serge

  公开号：US20060014779A1

  公开（公告）日：2006-01-19

  There is provided a compound of formula (I) wherein A is selected from —O— and —S—; X is selected from C 2 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl and C 4 -C 8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl-S(O) n — where n is 0, 1 or 2 , —CF 3 , —CN and —CONH 2 ; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3 -benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, 5 substituents each independently selected from halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkyl-S(O) n — where n is 0, 1 or 2 , nitro, acetyl, —CF 3 , —SCF 3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C 1 -C 4 alkyl; Z is selected from H, OR 3 or F, wherein R 3 is selected from H, C 1 -C 6 alkyl and phenyl C 1 -C 6 alkyl; R 1 and R 2 are each independently H or C 1 -C 4 alkyl; with the proviso that, when Z is H, then Y may not be optionally substituted phenyl or optionally substituted naphthyl.

  提供了一种化合物，其化学式为（I），其中A从—O—和—S—中选择；X从C2-C8烷基，C2-C8烯基，C3-C8环烷基和C4-C8环烷基烷基中选择，每种基团均可选用最多3个取代基，每个取代基可独立地从氯，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S（O）n-其中n为0，1或2，—CF3，—CN和—CONH2中选择；Y从苯基，萘基，二氢苯并噻吩基，苯并噻唑基，苯并异噻唑基，喹啉基，异喹啉基，萘啉基，噻吩基，茚基，1,3-苯并二氧杂环基，苯并噻吩基，吲哚基和苯并呋喃基中选择，每种基团均可选用最多4个或在可能的情况下最多5个取代基，每个取代基可独立地从氯，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S（O）n-其中n为0，1或2，硝基，乙酰基，— ，—S 和氰基中选择；当Y为吲哚基时，它可以被一个N-取代基所取代，所述取代基从C1-C4烷基中选择；Z从H，OR3或F中选择，其中R3从H，C1-C6烷基和苯基C1-C6烷基中选择；R1和R2各自独立地为H或C1-C4烷基；但是，当Z为H时，Y可能不是可选取代的苯基或可选取代的萘基。
• Heteroaryloxy 3-substituted propanamines s serotonin and norepinephrine reuptake inhibitors
  申请人：——

  公开号：US20040176435A1

  公开（公告）日：2004-09-09

  There is provided a heretoaryloxy 3-substituted propanamine compound of formula (I): wherein A is selected from —O— and —S—; X is selected from phenyl optionally substituted with up to 5 substituents selected from halo, C 1 -C 4 alkyl and C 1 -C 4 alkoxy, and thienyl optionally substituted with up to 3 substituents selected from halo and C 1 -C 4 alkyl; Y is selected from benzothienyl, indolyl and benzofuranyl, optionally substituted with up to 5 substituents selected from halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, nitro, acetyl and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C 1 -C 4 alkyl; R 1 and R 2 are each independently H or C 1 -C 4 alkyl; and pharmaceutically acceptable salts thereof. 1

  提供了一个式为（I）的3-取代丙胺基偶氧基化合物： 其中，A选择自—O—和—S—; X选择自苯基，可选地取代有高达5个卤素、C1-C4烷基和C1-C4烷氧基，和噻吩基，可选地取代有高达3个卤素和C1-C4烷基; Y选择自苯并噻吩基、吲哚基和苯并呋喃基，可选地取代有高达5个卤素、C1-C4烷基、C1-C4烷氧基、硝基、乙酰基和氰基; 当Y为吲哚基时，它可以被C1-C4烷基的N-取代基替代或进一步取代; R1和R2各自独立地为H或C1-C4烷基;以及其药学上可接受的盐。
• 3-aryloxy/thio-3-substituted propanamines and their use in inhibiting serotonin and norepinephrine reuptake
  申请人：Eli Lilly and Company

  公开号：US07417064B2

  公开（公告）日：2008-08-26

  There is provided a compound of formula (I) wherein A is selected from —O— and —S—; X is selected from C2-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl and C4-C8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n— where n is 0, 1 or 2, —CF3, —CN and —CONH2; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3-benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, 5 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n— where n is 0, 1 or 2, nitro, acetyl, —CF3, —SCF3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; Z is selected from H, OR3 or F, wherein R3 is selected from H, C1-C6 alkyl and phenyl C1-C6 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; with the proviso that, when Z is H, then Y may not be optionally substituted phenyl or optionally substituted naphthyl.

  提供了一个化合物的公式（I），其中A从- O-和-S-中选择；X从C2-C8烷基，C2-C8烯基，C3-C8环烷基和C4-C8环烷基烷基中选择，每个基团都可以选择性地取代高达3个取代基，每个取代基都是独立选择的，从卤素，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S（O）n-其中n为0,1或2，-CF3，-CN和-CONH2; Y从苯，萘，二氢苯并噻吩基，苯并噻唑基，苯并异噻唑基，喹啉基，异喹啉基，萘啉基，噻吩基，茚基，1,3-苯并二氧杂环基，苯并噻吩基，吲哚基和苯并呋喃基中选择，每个基团都可以选择性地取代高达4个或，在可能的情况下，5个取代基，每个取代基都是独立选择的，从卤素，C1-C4烷基，C1-C4烷氧基，C1-C4烷基-S（O）n-其中n为0,1或2，硝基，乙酰基，- ，-S 和氰基;当Y是吲哚基时，它可以被取代或进一步取代一个N-取代基，该取代基选择自C1-C4烷基; Z从H，OR3或F中选择，其中R3从H，C1-C6烷基和苯基C1-C6烷基中选择; R1和R2各自独立地是H或C1-C4烷基;前提是，当Z是H时，Y不能是选择性地取代的苯基或选择性地取代的萘基。