N-(2-hydroxy-2-phenylethyl)-4-quinolinamine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(2-hydroxy-2-phenylethyl)-4-quinolinamine
• 英文别名: 1-phenyl-2-(4-quinolinylamino)ethanol；1-phenyl-2-(quinolin-4-ylamino)ethanol
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: HIBJZSMQSFUEGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-2-phenylethyl)-4-quinolinamine 以8.7%的产率得到3-Chloro-N-(2-chloro-2-phenylethyl)-4-quinolinamine
  参考文献：
  名称：

  Substituted quinolines and cinnolines as fungicides

  摘要：

  一种杀真菌的方法，其包括向植物病原体的部位施用公式（1）化合物的真菌杀灭有效但不会对植物有害的量，其中：R.sup.1至R.sup.4独立地为H，卤素，（C.sub.1-C.sub.4）烷基，分支（C.sub.3-C.sub.4）烷基，卤代（C.sub.1-C.sub.4）烷基，（C.sub.1-C.sub.4）烷氧基，NO.sub.2或HN.sub.2，其中至少两个R.sup.1至R.sup.4为H，或者R.sup.2至R.sup.4中的一个为--NR.sup.7--Y--Ar或O--Y--Ar，其余的R.sup.1至R.sup.4为H；W为N或CR.sup.5；R.sup.5为H，CH.sub.3，Cl，O--Y--Ar或--NR.sup.7--Y--Ar；R.sup.6为H，CH.sub.3，Cl或Br；A为--O--Alk或--X--Y--Ar；Alk为C.sub.2-C.sub.18饱和或不饱和的烃链，直链或支链，可选择地用卤素，卤代（C.sub.1-C.sub.4）烷氧基，（C.sub.3-C.sub.8）环烷基，羟基或乙酰基取代；X为O，NR.sup.7或CR.sup.8R.sup.9，但如果R.sup.2至R.sup.5中的一个为NR.sup.7--Y--Ar或O--Y--Ar，则X--Y--Ar为相同的基团；R.sup.7为H，（C.sub.1-C.sub.4）烷基或乙酰基；R.sup.8和R.sup.9独立地为H，（C.sub.1-C.sub.4）烷基，卤素或羟基，或R.sup.8和R.sup.9结合形成包含三至七个碳原子的饱和或不饱和碳环；Y为2至8个碳原子的烷基链，可选地包括O，S，SO，SO.sub.2或NR.sup.7基团，并可选地包括包含三至七个碳原子的饱和或不饱和碳环，并可选地用（C.sub.1-C.sub.3）烷基，（C.sub.1-C.sub.4）烯基，苯基，（C.sub.3-C.sub.8）环烷基，羟基，卤素或乙酰基取代；Ar为芳基基团。

  公开号：

  US05114939A1
• 作为产物：
  描述：

  7-chloro-N-(2-hydroxy-2-phenylethyl)-4-quinolinamine 、 甲烷 、 sodium acetate 、 氢气 在 钯 水 、 异丙醇 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 25.0 ℃ 、45.96 MPa 条件下， 生成 N-(2-hydroxy-2-phenylethyl)-4-quinolinamine
  参考文献：
  名称：

  Dihydro-1,4-oxazino(2,3-C)quinolines

  摘要：

  公开了一种新化合物，其化学式为##STR1##其中X是氢，低烷基，低烷氧基，羟基，卤素，硝基或三氟甲基;R.sub.1是氢或低烷基;R.sub.2是氢，低烷基，芳基低烷基或--(CH.sub.2).sub.m R.sub.7，其中m为1、2或3，R.sub.7为氰基或氨基;R.sub.3和R.sub.4独立地是氢或低烷基;R.sub.5和R.sub.6独立地是氢或低烷基，或R.sub.5+R.sub.6与它们所连接的碳原子组成环丁烷，环戊烷，环己烷，环庚烷，吡咯烷，哌嗪烷，吗啉或硫代吗啉环，或R.sub.5是氢，R.sub.6是芳基或--CH.sub.2 OR.sub.8，其中R.sub.8是氢，低烷基或低烷基羰基，这些化合物对增强记忆有用。

  公开号：

  US04743601A1

文献信息

• Dihydro-4(hydroxyalkyeneamino)quinolines
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05182275A1

  公开（公告）日：1993-01-26

  There are disclosed novel compounds of the formula ##STR1## where X is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, nitro or trifluoromethyl; R.sub.1 is hydrogen or loweralkyl; R.sub.2 is hydrogen, loweralkyl, arylloweralkyl or --(CH.sub.2).sub.m R.sub.7 wherein m is 1, 2 or 3 and R.sub.7 is cyano or amino; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R.sub.5 and R.sub.6 are independently hydrogen or loweralkyl, or R.sub.5 +R.sub.6 taken together with the carbon atom to which they are attached constitute a cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyrrolidine, piperidine, morpholine or thiomorpholine ring, or R.sub.5 is hydrogen and R.sub.6 is aryl or --CH.sub.2 OR.sub.8 wherein R.sub.8 is hydrogen, loweralkyl or loweralkylcarbonyl, which are useful for enhancing memory.

  本发明公开了一种新型化合物的结构式，其中X为氢、低烷基、低烷氧基、羟基、卤素、硝基或三氟甲基；R1为氢或低烷基；R2为氢、低烷基、芳基低烷基或-(CH2)mR7，其中m为1、2或3，R7为氰基或氨基；R3和R4独立地为氢或低烷基；R5和R6独立地为氢或低烷基，或R5 + R6与它们附着的碳原子一起构成环丁烷、环戊烷、环己烷、环庚烷、吡咯烷、哌嗪烷、吗啉或硫代吗啉环，或R5为氢且R6为芳基或-CH2OR8，其中R8为氢、低烷基或低烷基羰基，这些化合物对增强记忆有用。
• Hydroxyquinoline amines, and method of enhancing memory in mammals
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04942168A1

  公开（公告）日：1990-07-17

  There are disclosed novel compounds of the formula ##STR1## where X is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, nitro or trifluoromethyl; R.sub.1 is hydrogen or loweralkyl; R.sub.2 is hydrogen, loweralkyl, arylloweralkyl or --(CH.sub.2).sub.m R.sub.7 wherein m is 1, 2 or 3 and R.sub.7 is cyano or amino; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R.sub.5 and R.sub.6 are independently hydrogen or loweralkyl, or R.sub.5 +R.sub.6 taken together with the carbon atom to which they are attached constitute a cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyrrolidine, piperidine, morpholine or thiomorpholine ring, or R.sub.5 is hydrogen and R.sub.6 is aryl or --CH.sub.2 OR.sub.8 wherein R.sub.8 is hydrogen, loweralkyl or loweralkylcarbonyl, which are useful for enhancing memory.

  本发明公开了一种新型化合物，其化学式为##STR1##其中X为氢、低碳基、低氧基、羟基、卤素、硝基或三氟甲基；R.sub.1为氢或低碳基；R.sub.2为氢、低碳基、芳基低碳基或--(CH.sub.2).sub.m R.sub.7，其中m为1、2或3，R.sub.7为氰基或氨基；R.sub.3和R.sub.4分别为氢或低碳基；R.sub.5和R.sub.6分别为氢或低碳基，或R.sub.5+R.sub.6与它们附着的碳原子一起构成环丁烷、环戊烷、环己烷、环庚烷、吡咯烷、哌嗪烷、吗啉或硫代吗啉环，或R.sub.5为氢，R.sub.6为芳基或--CH.sub.2 OR.sub.8，其中R.sub.8为氢、低碳基或低碳基酰基，其对增强记忆有用。
• Dihydro-1,4-oxazino(2,3-C)quinolines
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04743601A1

  公开（公告）日：1988-05-10

  There are disclosed novel compounds of the formula ##STR1## where X is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, nitro or trifluoromethyl; R.sub.1 is hydrogen or loweralkyl; R.sub.2 is hydrogen, loweralkyl, arylloweralkyl or --(CH.sub.2).sub.m R.sub.7 wherein m is 1, 2 or 3 and R.sub.7 is cyano or amino; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R.sub.5 and R.sub.6 are independently hydrogen or loweralkyl, or R.sub.5 +R.sub.6 taken together with the carbon atom to which they are attached constitute a cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyrrolidine, piperidine, morpholine or thiomorpholine ring, or R.sub.5 is hydrogen and R.sub.6 is aryl or --CH.sub.2 OR.sub.8 wherein R.sub.8 is hydrogen, loweralkyl or loweralkylcarbonyl, which are useful for enhancing memory.

  公开了一种新化合物，其化学式为##STR1##其中X是氢，低烷基，低烷氧基，羟基，卤素，硝基或三氟甲基;R.sub.1是氢或低烷基;R.sub.2是氢，低烷基，芳基低烷基或--(CH.sub.2).sub.m R.sub.7，其中m为1、2或3，R.sub.7为氰基或氨基;R.sub.3和R.sub.4独立地是氢或低烷基;R.sub.5和R.sub.6独立地是氢或低烷基，或R.sub.5+R.sub.6与它们所连接的碳原子组成环丁烷，环戊烷，环己烷，环庚烷，吡咯烷，哌嗪烷，吗啉或硫代吗啉环，或R.sub.5是氢，R.sub.6是芳基或--CH.sub.2 OR.sub.8，其中R.sub.8是氢，低烷基或低烷基羰基，这些化合物对增强记忆有用。
• Dihydro-1,4-oxazino(2,3-c)quinolines, a process and intermediates for the preparation thereof and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0299345A2

  公开（公告）日：1989-01-18

  The present application relates to compounds of the formula I where X is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, nitro or trifluoromethyl; R₁ is hydrogen or loweralkyl; R₂ is hydrogen, loweralkyl, arylloweralkyl or -(CH₂)mR₇ wherein m is 1, 2 or 3 and R₇ is cyano or amino; R₃ and R₄ are independently hydrogen or loweralkyl; R₅ and R₆ are independently hydrogen or loweralkyl, or R₅+R₆ taken together with the carbon atom to which they are attached constitute a cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyrrolidine, piperidine, morpholine or thiomorpholine ring, or R₅ is hydrogen and R₆ is aryl or -CH₂OR₈ wherein R₈ is hydrogen, loweralkyl or loweralkylcarbonyl, which are useful for enhancing memory. and a process for their preparation. The invention relates also to compounds of the formula II where X, R₁ and R₃ through R₆ are as defined earlier and R₉ is hydrogen or bromine (with the proviso that when R₁=R₃=R₄=R₅=R₆=R₉=H, X is not 7-chloro) which are also useful for enhancing memory and for preparing compounds of formula I.

  本申请涉及式 I 的化合物 其中 X 是氢、低级烷基、低级烷氧基、羟基、卤素、硝基或三氟甲基；R₁ 是氢或低级烷基；R₂ 是氢、低级烷基、芳基低级烷基或-(CH₂)mR₇，其中 m 是 1、2 或 3，R₇ 是氰基或氨基；R₃ 和 R₄ 独立地是氢或低级烷基；R₅ 和 R₆ 独立地为氢或低级烷基，或 R₅+R₆ 与它们所连接的碳原子一起构成环丁烷、环戊烷、环己烷、环庚烷吡咯烷、哌啶、吗啉或硫代吗啉环，或 R₅ 为氢且 R₆ 为芳基或 -CH₂OR₈ 其中 R₈ 为氢、低级烷基或低级烷基羰基。及其制备工艺。 本发明还涉及式 II 的化合物 其中 X、R₁ 和 R₃ 至 R₆ 如前定义，R₉ 是氢或溴 (但当 R₁=R₃=R₄=R₅=R₆=R₉=H 时，X 不是 7-氯)，这些化合物也有助于增强记忆力和制备式 I 的化合物。
• Substituted quinolines and cinnolines
  申请人：DowElanco

  公开号：EP0326331A2

  公开（公告）日：1989-08-02

  Compounds of the formula (1): wherein: R1 to R4 are independently H, halo, (C1-C4) alkyl, branched (C3-C4) alkyl, halo (C1-C4) alkyl, (C1-C4) alkoxy, N02, or NH2, at least two of R1 to R4 being H, or one of R2 to R4 is -NR7-Y-Ar or O-Y-Ar and the rest of R1 to R4 are H; W is N, or CR5; R5 is H, CH3, Cl, 0-Y-Ar, or -NR7-Y-Ar; R6 is H, CH3, Cl or Br; A is -O-Alk or -X-Y-Ar; Alk is a C2-C18 saturated or unsaturated hydrocarbon chain, straight chain or branched, optionally substituted with halo, halo (Ci-C4) alkoxy, (C3-C8) cycloalkyl, hydroxy, or acetyl; X is O, NR7, or CR8R9, provided that if one of R2 to R5 is NR7-Y-Ar or O-Y-Ar, then X-Y-Ar is an identical group; R7 is H, (C1-C4) alkyl, or acetyl; R8 and R9 are independently H, (Ci-C4) alkyl. (C1-C4) acyl, halo, or OH, or R8 and R9 combine to form a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms; Y is an alkylene chain 2 to 8 carbon atoms long, optionally including an O, S, SO, S02, or NR7 group or a saturated or unsaturated carbocyclic ring comprising three to seven carbon atoms, or substituted with (C1-C3) alkyl, (C2-C4) alkenyl, phenyl, (C3-C8) cycloalkyl, hydroxy, halo, or (Ci-C4) acyl; and Ar is 1,3-benzodioxolyl fluorenyl, pyridyl, imidazolyl, indolyl, thienyl. optionally substituted with CH3 or Cl, thiazolyl, cyclopentyl, 1-methylcyclopentyl, cyclohexenyl (hexahydrophenyl), cyclohexyl (tetrahydrophenyl), naphthyl, dihydronaphthyl, tetrahydronaphthyl, decahydronaphthyl, or a group of the formula (2): where R10 to R14 are independently H. halo. I. (C1-C10) alkyl, branched (C3-C6) alkyl, halo (C1-C4) alkyl. (C1-C4) alkoxy, halo (C1-C4) alkoxy. phenoxy. substituted phenoxy, phenylthio, substituted phenylthio, phenyl. substituted phenyl. N02, NH2, acetoxy, OH, CN. or SiR15R16R17, OSir15, R16, R17, where R15, R16, and R17 are independently (C1-C4) alkyl or (C3-C4) branched alkyl, provided that unless each of R10 to R14 is F, CH3, or H, then at least two of R10 to R14 are H: or an acid addition salt of a compound of formula (1) or an N-oxide of a compound of formula (1) when W is CR5 are fungicides, insecticides, and miticides.

  式（1）化合物： 其中 R1 至 R4 独立地为 H、卤代、（C1-C4）烷基、支链（C3-C4）烷基、卤代（C1-C4）烷基、（C1-C4）烷氧基、N02 或 NH2，R1 至 R4 中至少有两个为 H，或 R2 至 R4 中的一个为 -NR7-Y-Ar 或 O-Y-Ar，R1 至 R4 的其余部分为 H； W 是 N 或 CR5； R5 是 H、CH3、Cl、0-Y-Ar 或 -NR7-Y-Ar； R6 是 H、CH3、Cl 或 Br； A 是 -O-Alk 或 -X-Y-Ar； Alk 是 C2-C18 饱和或不饱和烃链，直链或支链，可选择被卤代、卤代（Ci-C4）烷氧基、（C3-C8）环烷基、羟基或乙酰基取代； X 是 O、NR7 或 CR8R9，但如果 R2 至 R5 中有一个是 NR7-Y-Ar 或 O-Y-Ar，则 X-Y-Ar 是相同的基团； R7 是 H、（C1-C4）烷基或乙酰基； R8 和 R9 独立地为 H、（Ci-C4）烷基或（C1-C4）酰基。(C1-C4)酰基、卤素或 OH，或 R8 和 R9 结合形成由 3 至 7 个碳原子组成的饱和或不饱和碳环； Y 是长度为 2 至 8 个碳原子的亚烷基链，可选择包括一个 O、S、SO、S02 或 NR7 基团，或包括 3 至 7 个碳原子的饱和或不饱和碳环，或被 (C1-C3) 烷基、(C2-C4) 烯基、苯基、(C3-C8) 环烷基、羟基、卤代或 (Ci-C4)酰基取代；以及 Ar 是 1,3-苯并二氧戊环 芴基 吡啶基 咪唑基 吲哚基 可选择被 CH3 或 Cl 取代的噻吩基，噻唑基 环戊基 1-甲基环戊基 环己烯基（六氢苯基）、 环己基（四氢苯基）、 萘基 二氢萘 四氢萘 十氢萘，或 式（2）的基团： 其中 R10 至 R14 独立地为 H、卤素。(C1-C10)烷基、支链(C3-C6)烷基、卤代(C1-C4)烷基。(C1-C4)烷氧基、卤代(C1-C4)烷氧基、苯氧基、取代苯氧基、苯硫基、取代苯硫基、苯基、取代苯基。N02、NH2、乙酰氧基、OH、CN 或 SiR15R16R17、OSir15、R16、R17，其中 R15、R16 和 R17 独立地是（C1-C4）烷基或（C3-C4）支链烷基，条件是除非 R10 至 R14 中的每一个都是 F、CH3 或 H，否则 R10 至 R14 中至少有两个是 H： 或式（1）化合物的酸加成盐 或式（1）化合物的 N-氧化物（当 W 为 CR5 时）是杀真菌剂、杀虫剂和杀螨剂。