3-[(E)-2-(4-tert-butylphenyl)vinyl]benzaldehyde | 1165795-93-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3-[(E)-2-(4-tert-butylphenyl)vinyl]benzaldehyde
• 英文别名: (E)-3-formyl-4'-tert-butylstilbene；3-[(E)-2-(4-tert-butylphenyl)ethenyl]benzaldehyde
• CAS: 1165795-93-6
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: PUNMOCMZDHBYHH-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  间溴苯甲醛 、 4-叔丁基苯乙烯 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 12.0h， 以5%的产率得到3-[(E)-2-(4-tert-butylphenyl)vinyl]benzaldehyde
  参考文献：
  名称：

  Size controlled synthesis of Pd nanoparticles in water and their catalytic application in C–C coupling reactions

  摘要：

  Catalytically active Pd nanoparticles have been synthesized in water by a novel reduction of Pd(II) with a Fischer carbene complex where polyethylene glycol (PEG) was used as stabilizer. PEG molecules wrap around the nanoparticles to impart stability and prevent agglomeration, yet leave enough surface area available on the nanoparticle for catalytic activity. Our method is superior to others in terms of rapid generation and stabilization of Pd nanoparticles in water with a cheap, readily available PEG stabilizer. The size of the nanoparticles generated can be controlled by the concentration of PEG in water medium. The size decreased with the increase in the PEG: Pd ratio. This aqueous nano-sized I'd is a highly efficient catalyst for Suzuki, Heck, Sonogashira, and Stille reaction. Water is Used as the only solvent for the coupling reactions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.062

文献信息

• [EN] EFFLUX-PUMP INHIBITORS AND THERAPEUTIC USES THEREOF<br/>[FR] INHIBITEURS DE LA POMPE À EFFLUX ET UTILISATIONS THÉRAPEUTIQUES CORRESPONDANTES
  申请人：BASILEA PHARMACEUTICA AG

  公开号：WO2016198691A1

  公开（公告）日：2016-12-15

  The present invention relates to compounds of formula I or pharmaceutically acceptable salt, solvate or hydrate thereof, wherein ASC is -N(R8)(R9)ASC-1 ASC-1 is Ring A represents a 4- to 6-membered saturated ring containing carbon atoms as ring members in addition to the nitrogen atom and wherein one CH2 moiety in ring A is optionally replaced by CH(R21) and wherein one carbon atom in ring A that is not adjacent to the nitrogen atom is optionally replaced by O, and wherein ring A is connected to X via a carbon atom; X represents a bond, -CH2- or -C(=O)-; ARl, AR2 represent independently phenyl or a 5- to 6- membered heteroaryl ring containing one to three heteroatoms selected from O, S and N, wherein AR1 is connected to LI via a carbon atom, and wherein AR2 is connected to L1 and L2 via a carbon atom; R1, R2, R3 represent independently hydrogen, halogen, cyano, hydroxyl, C1-C6alkyl, C1-C6haloalkyl, C3- C8cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, -C1-C6alkylene-N(R12)R13, -N(R12)R13, -C(O)OR11l, - C(O)N(R12)R13, -S(O)OR11 or phenyl; R4 represents hydroxyl, hydrogen, halogen, nitro, cyano, amino, C1-C6alkyl optionally substituted by 1 to 5 R14, C2-C6alkenyl optionally substituted by 1 to 5 R14, C2-C6alkynyl optionally substituted by 1 to 5 R14, C1-C6alkoxy optionally substituted by 1 to 5 R14, C2-C6alkenyloxy optionally substituted by 1 to 5 R14, C2-C6alkynyloxy optionally substituted by 1 to 5 R14, -C(O)OR15, -CHO, -C(O)N(R16)R17, -C1- C6alkylene-N(R9)(R16)R17, -O-Cycle-P or -O-Cycle-Q; R5, R6, R7 represent independently hydrogen, halogen, cyano, Cl-C6alkyl, C1-C6haloalkyl, Cl-C6alkoxy or C1-C6haloalkoxy; R8 represents hydrogen, methyl or ASC-1; R9 is methyl or absent, and wherein when R9 is present the respective nitrogen atom carries a positive charge; R10 represents hydrogen or methyl; Rl11 represents independently at each occurrence hydrogen or C1-C6alkyl; R12, R13 represent independently at each occurrence hydrogen or C1-C6alkyl; R14 represents independently at each occurrence halogen, cyano, hydroxyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C8cycloalkyl, -C(O)OR11, -CHO, -C(O)N(R12)R13, -C1-C6alkylene-N(R12)R13, Cycle-P, O-Cycle-P, Cycle-Q or O-Cycle-Q; Cycle-P represents independently at each occurrence a saturated or partially unsaturated C3-C8 carbocyclic ring optionally substituted by 1 to 3 R18, or a saturated or partially unsaturated C3-C8 heterocyclic ring optionally substituted by 1 to 3 Rl 8 containing carbon atoms as ring members and one or two ring members independently selected from N(R9)(R12), N(R9) and O; Cycle-Q represents independently at each occurrence phenyl optionally substituted by 1 to 3 R19 or a 5- to 6-membered heteroaryl ring containing one to four heteroatoms selected from O, S and N, optionally substituted by 1 to 3 R19; R15 represents independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R16 and R17 represent independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R18 and R19 represent independently at each occurrence halogen, cyano, hydroxyl, oxo, amino, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, Cl-C4haloalkoxy or -CO(O)R11; R20 represents independently at each occurrence hydrogen or methyl; R21 represents N(R20)2 or CH2-N(R20)2; LI represents -CH=CH-, -CH2-O-, -O-CH2-, -CH2-O-CH2-,-CH2-S-, -S-CH2-, -CH2-S(O)-, -CH2-S(O2)-, -S(O)-CH2-; -S(O2)-CH2-, -C(CH3)(CH3)-, -C(=O)-NH-, -NH-C(=O)-, -CH2-CH2-, -CH=CH-CH2-, - CH2-NH-C(=O)-, -C(=O)-NH-CH2, -C≡C-, -S(O2)-NH-CH2-, -S(02)-NH, -O-CH2-CH2-O-, -O-, -NH- CH2-, -CH2-NH-, -CH2-CH2-O-, or -NH-C(=O)-CH2-O-, or a bond; L2 represents Cl-C7alkylene, wherein one or more CH2 moieties in the alkylene are optionally replaced independently by -N(R9)(R20)-, -CH(N(R9)(R20)(R20))-, or -C(=0)-, wherein within L2 there are no adjacent C(=O) moieties or adjacent -N(R9)(R20)- moieties, and wherein the terminal moiety of L2 is not - N(R9)(R20)-, or L2 represents -O-C1-C6alkylene-, or L2 represents a bond, providing that X represents - CH2- when L2 is a bond; as well as methods of using the compounds of formula I for treating or preventing bacterial infections.

  本发明涉及以下公式I的化合物或其药学上可接受的盐、溶剂或水合物，其中ASC为-N(R8)(R9)ASC-1，ASC-1为环A，表示一个含有碳原子的4-至6-成员饱和环，除氮原子外还包含碳原子，并且环A中的一个CH2基团可以选择性地被CH(R21)取代，环A中的一个非邻氮原子的碳原子可以选择性地被氧取代，环A通过一个碳原子连接到X；X表示一个键，- -或-C(=O)-；AR1、AR2独立表示苯基或一个含有1至3个氧、硫和氮的杂环的5至6-成员环，其中AR1通过一个碳原子连接到L1，AR2通过一个碳原子连接到L1和L2；R1、R2、R3独立表示氢、卤素、氰基、羟基、C1-C6烷基、C1-C6卤代烷基、C3-C8环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、-C1-C6烷基-N(R12)R13、-N(R12)R13、-C(O)OR11l、-C(O)N(R12)R13、-S(O)OR11或苯基；R4表示羟基、氢、卤素、硝基、氰基、氨基、C1-C6烷基，可选地被1至5个R14取代，C2-C6烯基，可选地被1至5个R14取代，C2-C6炔基，可选地被1至5个R14取代，C1-C6烷氧基，可选地被1至5个R14取代，C2-C6烯氧基，可选地被1至5个R14取代，C2-C6炔氧基，可选地被1至5个R14取代，-C(O)OR15，-CHO，-C(O)N(R16)R17，-C1-C6烷基-N(R9)(R16)R17，-O-Cycle-P或-O-Cycle-Q；R5、R6、R7独立表示氢、卤素、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基；R8表示氢、甲基或ASC-1；R9为甲基或不存在，当R9存在时，相应的氮原子带有正电荷；R10表示氢或甲基；Rl11独立表示每次出现的氢或C1-C6烷基；R12、R13独立表示每次出现的氢或C1-C6烷基；R14独立表示每次出现的卤素、氰基、羟基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C8环烷基、-C(O)OR11、-CHO、-C(O)N(R12)R13、-C1-C6烷基-N(R12)R13、Cycle-P、O-Cycle-P、Cycle-Q或O-Cycle-Q；Cycle-P独立表示每次出现的饱和或部分不饱和的C3-C8碳环，可选地被1至3个R18取代，或者可选地被1至3个Rl 8取代的饱和或部分不饱和的C3-C8杂环，含有碳原子作为环成员，并且一个或两个环成员独立选择自N(R9)(R12)、N(R9)和O；Cycle-Q独立表示每次出现的苯环，可选地被1至3个R19取代，或者一个含有1至4个氧、硫和氮的5至6-成员杂环，可选地被1至3个R19取代；R15独立表示每次出现的氢或C1-C6烷基，可选地被1至5个R14取代；R16和R17独立表示每次出现的氢或C1-C6烷基，可选地被1至5个R14取代；R18和R19独立表示每次出现的卤素、氰基、羟基、氧、氨基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、Cl-C4卤代烷氧基或-CO(O)R11；R20独立表示每次出现的氢或甲基；R21表示N(R20)2或 -N(R20)2；LI表示-CH=CH-、- -O-、-O- -、- -O- -、- -S-、-S- -、- -S(O)-、- -S(O2)-、-S(O)- -、-S(O2)- -、-C(CH3)( )-、-C(=O)-NH-、-NH-C(=O)-、- - -、-CH=CH- -、- -NH-C(=O)-、-C(=O)-NH- 、-C≡C-、-S(O2)-NH- -、-S(02)-NH、-O- - -O-、-O-、-NH- -、- -NH-、- - -O-或-NH-C(=O)- -O-、或一个键；L2表示Cl-C7烷基，其中烷基中的一个或多个 基团可以选择性地独立地被-N(R9)(R20)-、-CH(N(R9)(R20)(R20))-或-C(=0)-取代，在L2内没有相邻的C(=O)基团或相邻的-N(R9)(R20)-基团，并且L2的末端基团不是-N(R9)(R20)-，或者L2表示-O-C1-C6烷基-，或者L2表示一个键，只要X在L2是一个键时表示- -；以及使用公式I的化合物治疗或预防细菌感染的方法。
• Efflux-pump inhibitors and therapeutic uses thereof
  申请人：Basilea Pharmaceutica International AG

  公开号：US10464896B2

  公开（公告）日：2019-11-05

  The present invention relates to compounds of formula I or pharmaceutically acceptable salt, solvate or hydrate thereof, wherein ASC is —N(R8)(R9)ASC-1 ASC-1 is Ring A represents a 4- to 6-membered saturated ring containing carbon atoms as ring members in addition to the nitrogen atom and wherein one CH2 moiety in ring A is optionally replaced by CH(R21) and wherein one carbon atom in ring A that is not adjacent to the nitrogen atom is optionally replaced by O, and wherein ring A is connected to X via a carbon atom; X represents a bond, —CH2- or —C(═O)—; AR1, AR2 represent independently phenyl or a 5- to 6-membered heteroaryl ring containing one to three heteroatoms selected from O, S and N, wherein AR1 is connected to L1 via a carbon atom, and wherein AR2 is connected to L1 and L2 via a carbon atom; R1, R2, R3 represent independently hydrogen, halogen, cyano, hydroxyl, C1-C6alkyl, C1-C6haloalkyl, C3-C8cycloalkyl, C1-C6alkoxy, C1-C6haloalkoxy, —C1-C6alkylene-N(R12)R13, —N(R12)R13, —C(O)OR111, —C(O)N(R12)R13, —S(O)OR11 or phenyl; R4 represents hydroxyl, hydrogen, halogen, nitro, cyano, amino, C1-C6alkyl optionally substituted by 1 to 5 R14, C2-C6alkenyl optionally substituted by 1 to 5 R14, C2-C6alkynyl optionally substituted by 1 to 5 R14, C1-C6alkoxy optionally substituted by 1 to 5 R14, C2-C6alkenyloxy optionally substituted by 1 to 5 R14, C2-C6alkynyloxy optionally substituted by 1 to 5 R14, —C(O)OR15, —CHO, —C(O)N(R16)R17, —C1-C6alkylene-N(R9)(R16)R17, —O-Cycle-P or —O-Cycle-Q; R5, R6, R7 represent independently hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy; R8 represents hydrogen, methyl or ASC-1; R9 is methyl or absent, and wherein when R9 is present the respective nitrogen atom carries a positive charge; R10 represents hydrogen or methyl; R11 represents independently at each occurrence hydrogen or C1-C6alkyl; R12, R13 represent independently at each occurrence hydrogen or C1-C6alkyl; R14 represents independently at each occurrence halogen, cyano, hydroxyl, C1-C6alkoxy, C1-C6haloalkoxy, C3-C8cycloalkyl, —C(O)OR11, —CHO, —C(O)N(R12)R13, —C1-C6alkylene-N(R12)R13, Cycle-P, O-Cycle-P, Cycle-Q or O-Cycle-Q; Cycle-P represents independently at each occurrence a saturated or partially unsaturated C3-C8 carbocyclic ring optionally substituted by 1 to 3 R18, or a saturated or partially unsaturated C3-C8 heterocyclic ring optionally substituted by 1 to 3 R18 containing carbon atoms as ring members and one or two ring members independently selected from N(R9)(R12), N(R9) and O; Cycle-Q represents independently at each occurrence phenyl optionally substituted by 1 to 3 R19 or a 5- to 6-membered heteroaryl ring containing one to four heteroatoms selected from O, S and N, optionally substituted by 1 to 3 R19; R15 represents independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R16 and R17 represent independently at each occurrence hydrogen or C1-C6alkyl optionally substituted by 1 to 5 R14; R18 and R19 represent independently at each occurrence halogen, cyano, hydroxyl, oxo, amino, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy or —CO(O)R11; R20 represents independently at each occurrence hydrogen or methyl; R21 represents N(R20)2 or CH2-N(R20)2; LI represents —CH═CH—, —CH2-O—, —O—CH2-, —CH2-O—CH2-, —CH2-S—, —S—CH2-, —CH2-S(O)—, —CH2-S(O2)-, —S(O)—CH2-; —S(O2)-CH2-, —C(CH3)(CH3)-, —C(═O)—NH—, —NH—C(═O)—, —CH2-CH2-, —CH═CH—CH2-, —CH2-NH—C(═O)—, —C(═O)—NH—CH2, —C≡C—, —S(O2)-NH—CH2-, —S(O2)-NH, —O—CH2-CH2-O—, —O—, —NH— CH2-, —CH2-NH—, —CH2-CH2-O—, or —NH—C(═O)—CH2-O—, or a bond; L2 represents C1-C7alkylene, wherein one or more CH2 moieties in the alkylene are optionally replaced independently by —N(R9)(R20)-, —CH(N(R9)(R20)(R20))-, or —C(═O)—, wherein within L2 there are no adjacent C(═O) moieties or adjacent —N(R9)(R20)— moieties, and wherein the terminal moiety of L2 is not —N(R9) (R20)-, or L2 represents —O—C1-C6alkylene-, or L2 represents a bond, providing that X represents —CH2- when L2 is a bond; as well as methods of using the compounds of formula I for treating or preventing bacterial infections.

  本发明涉及式I化合物或其药学上可接受的盐、溶液或水合物，其中ASC为-N(R8)(R9)ASC-1 ASC-1为 环A代表除氮原子外含有碳原子作为环成员的4至6元饱和环，其中环A中的一个CH2分子任选被CH(R21)取代，环A中不与氮原子相邻的一个碳原子任选被O取代，其中环A通过一个碳原子与X连接；X代表键、- -或-C(═O)-； AR1、AR2 独立地代表苯基或含有一至三个选自 O、S 和 N 的杂原子的 5 至 6 元杂芳基环，其中 AR1 通过一个碳原子与 L1 连接，AR2 通过一个碳原子与 L1 和 L2 连接；R1、R2、R3 独立地代表氢、卤素、氰基、羟基、C1-C6 烷基、C1-C6 卤代烷基、C3-C8 环烷基、C1-C6 烷氧基、C1-C6 卤代烷氧基、-C1-C6 亚烷基-N(R12)R13、-N(R12)R13、-C(O)OR111、-C(O)N(R12)R13、-S(O)OR11 或苯基；R4 代表羟基、氢、卤素、硝基、氰基、氨基、被 1 至 5 个 R14 任选取代的 C1-C6 烷基、被 1 至 5 个 R14 任选取代的 C2-C6 烯基、被 1 至 5 个 R14 任选取代的 C2-C6 烷炔基、被 1 至 5 个 R14 任选取代的 C1-C6 烷氧基、被 1 至 5 个 R14 任选取代的 C2-C6 烷氧基、被 1 至 5 个 R14 任选取代的 C2-C6 烷炔氧基、-C(O)OR15、-CHO、-C(O)N(R16)R17、-C1-C6 亚烷基-N(R9)(R16)R17、-O-Cycle-P 或 -O-Cycle-Q；R5、R6、R7 独立地代表氢、卤素、氰基、C1-C6烷基、C1-C6 卤代烷基、C1-C6 烷氧基或 C1-C6 卤代烷氧基；R8 代表氢、甲基或 ASC-1；R9 代表甲基或不存在，其中当 R9 存在时，相应的氮原子带有正电荷；R10 代表氢或甲基；R11 在每次出现时独立地代表氢或 C1-C6 烷基；R12、R13在每次出现时独立地代表氢或C1-C6烷基；R14在每次出现时独立地代表卤素、氰基、羟基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C8环烷基、-C(O)OR11、-CHO、-C(O)N(R12)R13、-C1-C6亚烷基-N(R12)R13、Cycle-P、O-Cycle-P、Cycle-Q或O-Cycle-Q；Cycle-P 在每次出现时独立地代表被 1 至 3 个 R18 任选取代的饱和或部分不饱和 C3-C8 碳环，或被 1 至 3 个 R18 任选取代的饱和或部分不饱和 C3-C8 杂环，该杂环含有作为环成员的碳原子和一个或两个独立选自 N(R9)(R12)、N(R9) 和 O 的环成员；Cycle-Q 在每次出现时均独立地代表被 1 至 3 个 R19 任选取代的苯基或含有 1 至 4 个选自 O、S 和 N 的杂原子的 5 至 6 元杂芳基环；R15 独立地在每次出现时代表氢或被 1 至 5 个 R14 任选取代的 C1-C6 烷基；R16 和 R17 独立地在每次出现时代表氢或被 1 至 5 个 R14 任选取代的 C1-C6 烷基；R18 和 R19 独立地在每次出现时代表卤素、氰基、羟基、氧代、氨基、C1-C4 烷基、C1-C4 卤代烷基、C1-C4 烷氧基、C1-C4 卤代烷氧基或-CO(O)R11；R20 独立地在每次出现时代表氢或甲基；R21 代表 N(R20)2 或 -N(R20)2； LI 代表 -CH═CH-、- -O-、-O- -、- -O- -、- -S-、-S- -、- -S(O)-、- -S(O2)-、-S(O)- -；-S(O2)- -，-C(CH3)( )-，-C(═O)-NH-，-NH-C(═O)-，- - -，-CH═ -，- -NH-C(═O)-，-C(═O)-NH- ，-C≡C-、-S(O2)-NH- -，-S(O2)-NH，-O- - -O-，-O-，-NH- -，- -NH-，- - -O-，或-NH-C(═O)- -O-，或键；L2 代表 C1-C7 亚烷基，其中亚烷基中的一个或多个 基团可选择地独立地被 -N(R9)(R20)-、-CH(N(R9)(R20)(R20))- 或 -C(═O)-取代，其中在 L2 内没有相邻的 C(═O) 基团或相邻的 -N(R9)(R20)- 基团、其中 L2 的末端分子不是-N(R9) (R20)-，或者 L2 代表-O-C1-C6 亚烷基-，或者 L2 代表键，条件是当 L2 为键时 X 代表- -；以及使用式 I 化合物治疗或预防细菌感染的方法。
• EFFLUX-PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
  申请人：Basilea Pharmaceutica International AG

  公开号：EP3307725A1

  公开（公告）日：2018-04-18