1-(4-(benzyloxy)-3-methylphenyl)-2-bromoethanone | 56443-33-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(benzyloxy)-3-methylphenyl)-2-bromoethanone
• 英文别名: 4-benzyloxy-3-methyl-ω-bromoacetophenone；1-[4-(benzyloxy)-3-methylphenyl]-2-bromoethanone；2-bromo-1-(3-methyl-4-phenylmethoxyphenyl)ethanone
• CAS: 56443-33-5
• 化学式: C₁₆H₁₅BrO₂
• 分子量: 319.198
• InChiKey: FTQYNEKKQMCMHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-(benzyloxy)-3-methylphenyl)-2-bromoethanone 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 生成 2-(4-hydroxy-2-methylphenyl)-2-oxoethyl-4-(tert-butoxycarbonylamino)butanoate
  参考文献：
  名称：

  p-Hydroxyphenacyl photoremovable protecting groups — Robust photochemistry despite substituent diversity

  摘要：

  一项关于各种取代基对对羟基苯乙酯光化学重排影响的广泛研究表明，常见取代基（如 F、MeO、CN、CO2R、CONH2 和 CH3）对光-Favorskii 重排和酸离去基团释放的速率和量子效率影响很小，对反应三重态的寿命影响也很小。当光解在缓冲水介质中进行时，pH 值超过发色团的基态 pKao（其中共轭碱是主要形式），则释放和重排的量子产率在所有取代基中都会降低。否则，取代基对这些坚固发色团的光反应影响很小。

  DOI：

  10.1139/v10-143
• 作为产物：
  描述：

  4-羟基-3-甲基苯乙酮 在 盐酸 、 氢氧化钾 、 四乙基碘化铵 、 溴 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1-(4-(benzyloxy)-3-methylphenyl)-2-bromoethanone
  参考文献：
  名称：

  Goswami, Jonalee; Goswami, Amrit, Journal of the Indian Chemical Society, 2002, vol. 79, # 5, p. 469 - 471

  摘要：

  DOI：

文献信息

• [EN] (THIO)MORPHOLINE DERIVATIVES AS S1P MODULATORS<br/>[FR] DÉRIVÉS DE (THIO)MORPHOLINE MODULATEURS DE S1P
  申请人：ABBOTT HEALTHCARE PRODUCTS BV

  公开号：WO2011023795A1

  公开（公告）日：2011-03-03

  The present invention relates to (thio)morpholine derivatives of the formula (I), wherein R1 is selected from cyano, (2-4C)alkynyl, (1-4C)alkyl, (3-6C)cycloalkyl, (4-6C)cycloalkenyl, (6-8C)bicycloalkyl, (8-10C)bicyclic group, each optionally substituted with (1-4C)alkyl, phenyl, biphenyl, naphthyl, each optionally substituted with one or more substituents independently selected from halogen, (1-4C)alkyloptionally substituted with one or more fluoro atoms, (2-4C)alkynyl, (1-4C)alkoxy optionally substituted with one or more fluoro atoms,amino, di(1-4C)alkylamino, -SO2-(1-4C)alkyl, -CO-(1-4C)alkyl, -CO-O-(1-4C)alkyl, -NH-CO-(1-4C)alkyl and (3-6C)cycloalkyl, phenyl substituted with phenoxy, benzyl, benzyloxy, phenylethyl or monocyclic heterocycle, each optionally substituted with (1-4C)alkyl, monocyclic heterocycle optionally substituted with halogen, (1-4C)alkyl or with phenyl optionally substituted with (1-4C)alkyl, and bicyclic heterocycle optionally substituted with (1-4C)alkyl; A is selected from -CO-O-, -O-CO-, -NH-CO-, -CO-NH, -C=C-, -CCH3-O- and the linking group –Y-(CH2)n-X- wherein Y is attached to R1 and selected from a bond, -O-, -S-, -SO-, -SO2-, -CH2-O-, -CO-, -O-CO-, -CO-O-, -CO-NH-, -NH-CO-, -C=C-and -C≡C-; n is an integer from 1 to 10; and X is attached to the phenylene / pyridyl group and selected from a bond, -O-, -S-, -SO-, -SO2 -, -NH, -CO-, -C=C-and -C≡C-; ring structure B optionally contains one nitrogen atom; R2 is H, (1-4C)alkyl optionally substituted with one or more fluoro atoms, (1-4C)alkoxy optionally substituted with one or more fluoro atoms, or halogen; and R3 is (1-4C)alkylene-R5 wherein the alkylene group may be substituted with (CH2)2 to form a cyclopropyl moiety or one or two halogen atoms, or R3 is is (3-6C)cycloalkylene-R5 or -CO-CH2-R5, wherein R5 is -OH, -PO3H2, -OPO3H2, -COOH, -COO(1-4C)alkyl or tetrazol-5-yl; R4 is H or (1-4C)alkyl; R6 is one or more substituents independently selected from H, (1-4C)alkyl or oxo; W is -O-, -S-, -SO- or -SO2-; or a pharmaceutically acceptable salt, a solvate or hydrate thereof; with the proviso that the derivative of formula (I) is not 2-(4-ethylphenyl)-4-morpholinoethanol or 4-[4-(2-hydroxyethyl)-2-morpholinyl]benzeneacetonitrile or a pharmaceutically acceptable salt, a solvate or hydrate thereof. The compounds of the invention have affinity to S1P receptors and may be used in the treatment, alleviation or prevention of S1P receptor mediated diseases and conditions.

  本发明涉及公式（I）的（硫）吗啉衍生物，其中R1从氰基，（2-4C）炔基，（1-4C）烷基，（3-6C）环烷基，（4-6C）环烯基，（6-8C）双环烷基，（8-10C）双环基团中选择，每个基团可选择地取代为（1-4C）烷基，苯基，联苯基，萘基，每个基团可选择地取代为一个或多个取代基，独立选择自卤素，（1-4C）烷基可选择地取代为一个或多个氟原子，（2-4C）炔基，（1-4C）氧烷基可选择地取代为一个或多个氟原子，氨基，二（1-4C）烷基氨基，-SO2-（1-4C）烷基，-CO-（1-4C）烷基，-CO-O-（1-4C）烷基，-NH-CO-（1-4C）烷基和（3-6C）环烷基，苯基取代为苯氧基，苄基，苄氧基，苯乙基或单环杂环烃，每个基团可选择地取代为（1-4C）烷基，单环杂环烃可选择地取代为卤素，（1-4C）烷基或取代为苯基的苯基，可选择地取代为（1-4C）烷基，和双环杂环烃可选择地取代为（1-4C）烷基；A从-CO-O-，-O-CO-，-NH-CO-，-CO-NH，-C=C-，-CCH3-O-和连接基-Y-（CH2）n-X-中选择，其中Y连接到R1并从键，-O-，-S-，-SO-，-SO2-，-CH2-O-，-CO-，-O-CO-，-CO-O-，-CO-NH-，-NH-CO-，-C=C-和-C≡C-中选择；n是1到10的整数；X连接到苯基/吡啶基团并从键，-O-，-S-，-SO-，-SO2-，-NH，-CO-，-C=C-和-C≡C-中选择；环结构B可选择地含有一个氮原子；R2是H，（1-4C）烷基可选择地取代为一个或多个氟原子，（1-4C）氧烷基可选择地取代为一个或多个氟原子，或卤素；R3是（1-4C）烷基-R5，其中烷基基团可取代为（CH2）2形成环丙基基团或一个或两个卤素原子，或R3是（3-6C）环烷基-R5或-CO-CH2-R5，其中R5是-OH，-PO3H2，-OPO3H2，-COOH，-COO（1-4C）烷基或四唑-5-基；R4是H或（1-4C）烷基；R6是一个或多个取代基，独立选择自H，（1-4C）烷基或氧代基；W是-O-，-S-，-SO-或-SO2-；或其药学上可接受的盐，溶剂或水合物；但是，公式（I）的衍生物不是2-（4-乙基苯基）-4-吗啉乙醇或4-[4-（2-羟乙基）-2-吗啉基]苯乙腈或其药学上可接受的盐，溶剂或水合物。本发明的化合物具有对S1P受体的亲和力，可用于治疗、缓解或预防S1P受体介导的疾病和症状。
• PHENYLIMIDAZOLE COMPOUNDS
  申请人：Shibutani Tadao

  公开号：US20110275823A1

  公开（公告）日：2011-11-10

  [Object] To provide a pharmaceutical product (chemotherapeutic agent) effective in the prevention and treatment of hyperlipidemia, obesity, etc. [Solving Means] A phenylimidazole compound represented by the following General Formula (1): wherein, R 1 represents a hydrogen atom, a phenyl lower alkyl group optionally having a substituent, or a pyridyl lower alkyl group optionally having a substituent, and the benzene ring and the pyridine ring are optionally substituted with 1 or 2 substituents selected from the group consisting of halogen atoms, cyano group and halogen-substituted lower alkyl groups. One of R 2 and R 3 represents a hydrogen atom and the other represents a lower alkoxy group. R 4 represents a phenyl group optionally having a substituent. R 5 and R 6 are the same or different, and represent a hydrogen atom or a lower alkyl group. R 7 and R 8 are the same or different, and represent a hydrogen atom or a lower alkoxy group. However, when R 1 represents an unsubstituted phenyl lower alkyl group, R 2 represents a lower alkoxy group, R 3 represents a hydrogen atom, R 4 represents a phenyl group optionally having a substituent, and R 5 represents a hydrogen atom, R 6 is not a hydrogen atom.

  提供一种在预防和治疗高脂血症、肥胖等方面有效的药物产品（化疗药物）。 解决方法是通过以下一般式（1）所代表的苯基咪唑化合物： 其中，R1代表氢原子、苯基较低烷基基团（可选地带有取代基）或吡啶基较低烷基基团（可选地带有取代基），苯环和吡啶环可选地带有来自卤原子、氰基和卤代较低烷基基团的1或2个取代基。R2和R3中的一个代表氢原子，另一个代表较低烷氧基团。R4代表可选地带有取代基的苯基团。R5和R6相同或不同，代表氢原子或较低烷基基团。R7和R8相同或不同，代表氢原子或较低烷氧基团。但是，当R1代表未取代的苯基较低烷基基团时，R2代表较低烷氧基团，R3代表氢原子，R4代表可选地带有取代基的苯基团，R5代表氢原子时，R6不是氢原子。
• [EN] 1-'2-(4-HYDROXYPHENYL)-2-HYDROXYETHYL!-PIPERIDIN-4-OL COMPOUNDS AS NMDA RECEPTOR ANTAGONISTS<br/>[FR] COMPOSES DE 1-[2-(4-HYDROXYPHENYL)-2-HYDROXYETHYL]-PIPERIDIN-4-OL EN TANT QU'ANTAGONISTES DU RECEPTEUR DU NMDA
  申请人：PFIZER JAPAN INC

  公开号：WO2005035522A1

  公开（公告）日：2005-04-21

  This invention provides a compound of the formula (I), wherein R1 and R2 independently represents a hydrogen atom or the like; R3 represents an aryl group having from 6 to 10 ring carbon or the like; said aryl groups having from 6 to 10 ring carbon atoms and said heteroaryl groups having from 5 to 10 atoms are unsubstituted or are substituted by at least one substituent selected from the group consisting of substituents a; said substituents a are selected from the group consisting of halogen atoms or the like; or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of NMDA NR2B receptor such of pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound.

  本发明提供了式(I)的化合物，其中R1和R2分别表示氢原子或类似物；R3表示具有6至10个环碳或类似物的芳基基团；所述芳基基团具有6至10个环碳原子和所述杂环芳基基团具有5至10个原子，未经取代或通过从取代基a的群组中选择至少一种取代基而被取代；所述取代基a被选择自卤素原子或类似物的群组；或该化合物的药学上可接受的酯或其药学上可接受的盐。这些化合物对于治疗由NMDA NR2B受体过度激活引起的疾病条件，如疼痛等在哺乳动物中很有用。本发明还提供了包含上述化合物的药物组合物。
• 1-'2-(4-Hydroxyphenyl)-2-hydroxyethyl!-piperidin-4-ol compounds as nmda receptor antagonists
  申请人：Ando Kazuo

  公开号：US20070021414A1

  公开（公告）日：2007-01-25

  This invention provides a compound of the formula (I), wherein R 1 and R 2 independently represents a hydrogen atom or the like; R 3 represents an aryl group having from 6 to 10 ring carbon or the like; said aryl groups having from 6 to 10 ring carbon atoms and said heteroaryl groups having from 5 to 10 atoms are unsubstituted or are substituted by at least one substituent selected from the group consisting of substituents a; said substituents a are selected from the group consisting of halogen atoms or the like; or a pharmaceutically acceptable ester of such compound, or a pharmaceutically acceptable salt thereof. These compounds are useful for the treatment of disease conditions caused by overactivation of NMDA NR2B receptor such of pain, or the like in mammalian. This invention also provides a pharmaceutical composition comprising the above compound.

  本发明提供了式(I)的化合物，其中R1和R2独立地表示氢原子或类似物；R3表示具有6至10个环碳或类似物的芳基基团；所述芳基基团具有6至10个环碳原子，所述杂环芳基基团具有5至10个原子，未被取代或被至少一种选择自取代物a的取代基组成的取代；所述取代基a是从卤原子或类似物的组中选择的；或其药学上可接受的酯或药学上可接受的盐。这些化合物对于治疗由NMDA NR2B受体过度激活引起的疾病状态如疼痛等在哺乳动物中具有用处。本发明还提供了包括上述化合物的制药组合物。
• (THIO)MORPHOLINE DERIVATIVES AS S1P MODULATORS
  申请人：Iwema Bakker Wouter I.

  公开号：US20120220552A1

  公开（公告）日：2012-08-30

  The present disclosure relates to (thio)morpholine derivatives of the formula (I) wherein R1 is selected from cyano, (2-4C)alkynyl, (1-4C)alkyl, (3-6C)cycloalkyl, (4-6C)cycloalkenyl, (6-8C)bicycloalkyl, (8-10C)bicyclic group, each optionally substituted with (1-4C)alkyl, phenyl, biphenyl, naphthyl, each optionally substituted with one or more substituents independently selected from halogen, (1-4C)alkyl optionally substituted with one or more fluoro atoms, (2-4C)alkynyl, (1-4C)alkoxy optionally substituted with one or more fluoro atoms, amino, di(1-4C)alkylamino, —SO 2 -(1-4C)alkyl, —CO-(1-4C)alkyl, —CO—O-(1-4C)alkyl, —NH—CO-(1-4C)alkyl and (3-6C)cycloalkyl, phenyl substituted with phenoxy, benzyl, benzyloxy, phenylethyl or monocyclic heterocycle, each optionally substituted with (1-4C)alkyl, monocyclic heterocycle optionally substituted with halogen, (1-4C)alkyl or with phenyl optionally substituted with (1-4C)alkyl, and bicyclic heterocycle optionally substituted with (1-4C)alkyl; A is selected from —CO—O—, —O—CO—, —NH—CO—, —CO—NH, —C═C—, —CCH 3 —O— and the linking group —Y—(CH 2 ) n —X— wherein Y is attached to R1 and selected from a bond, —O—, —S—, —SO—, —SO 2 —, —CH 2 —O—, —CO—, —O—CO—, —CO—O—, —CO—NH—, —NH—CO—, —C═C— and —C≡C—; n is an integer from 1 to 10; and X is attached to the phenylene/pyridyl group and selected from a bond, —O—, —S—, —SO—, —SO 2 —, —NH, —CO—, —C═C— and —C≡C—; ring structure B optionally contains one nitrogen atom; R2 is H, (1-4C)alkyl optionally substituted with one or more fluoro atoms, (1-4C)alkoxy optionally substituted with one or more fluoro atoms, or halogen; and R3 is (1-4C)alkylene-R5 wherein the alkylene group may be substituted with (CH 2 ) 2 to form a cyclopropyl moiety or one or two halogen atoms, or R3 is (3-6C)cycloalkylene-R5 or —CO—CH 2 —R5, wherein R5 is —OH, —PO 3 H 2 , —OPO 3 H 2 , —COOH, —COO(1-4C)alkyl or tetrazol-5-yl; R4 is H or (1-4C)alkyl; R6 is one or more substituents independently selected from H, (1-4C)alkyl or oxo; W is —O—, —S—, —SO— or —SO 2 —; or a pharmaceutically acceptable salt, a solvate or hydrate thereof; with the proviso that the derivative of formula (I) is not 2-(4-ethylphenyl)-4-morpholinoethanol or 4-[4-(2-hydroxyethyl)-2-morpholinyl]benzeneacetonitrile or a pharmaceutically acceptable salt, a solvate or hydrate thereof. The compounds of the disclosure have affinity to S1P receptors and may be used in the treatment, alleviation or prevention of S1P receptor mediated diseases and conditions.

  本公开涉及以下式子的(硫)吗啡啶衍生物(I)： 其中，R1从氰基，(2-4C)炔基，(1-4C)烷基，(3-6C)环烷基，(4-6C)环烯基，(6-8C)双环烷基，(8-10C)双环基中选择，每个基都可以选择性地被(1-4C)烷基，苯基，联苯基，萘基取代，每个基也可以选择性地被一个或多个取代基独立地选择，所述取代基包括卤素，(1-4C)烷基可选择地被一个或多个氟原子取代，(2-4C)炔基，(1-4C)烷氧基可选择性地被一个或多个氟原子取代，氨基，二(1-4C)烷基氨基，—SO2-(1-4C)烷基，—CO-(1-4C)烷基，—CO—O-(1-4C)烷基，—NH—CO-(1-4C)烷基和(3-6C)环烷基，苯基取代为苯氧基，苄基，苄氧基，苯乙基或单环杂环，每个基都可以选择性地被(1-4C)烷基取代，单环杂环可选择性地被卤素，(1-4C)烷基或苯基取代，或双环杂环可选择性地被(1-4C)烷基取代； A从—CO—O—，—O—CO—，—NH—CO—，—CO—NH，—C═C—，—CCH3—O—和连接基—Y—(CH2)n—X—中选择，其中Y连接到R1并从键，—O—，—S—，—SO—，—SO2—，—CH2—O—，—CO—，—O—CO—，—CO—O—，—CO—NH—，—NH—CO—，—C═C—和—C≡C—中选择；n是1到10的整数；X连接到苯基/吡啶基并从键，—O—，—S—，—SO—，—SO2—，—NH，—CO—，—C═C—和—C≡C—中选择；环结构B可选择性地包含一个氮原子； R2为H，(1-4C)烷基可选择性地被一个或多个氟原子取代，(1-4C)烷氧基可选择性地被一个或多个氟原子取代，或卤素； R3为(1-4C)烷基-R5，其中烷基可以被(CH2)2取代以形成环丙基基团或一或两个卤素原子，或R3为(3-6C)环烷基-R5或—CO—CH2—R5，其中R5为—OH，—PO3H2，—OPO3H2，—COOH，—COO(1-4C)烷基或四唑-5-基； R4为H或(1-4C)烷基； R6为一个或多个取代基，独立地选择自H，(1-4C)烷基或氧代基； W为—O—，—S—，—SO—或—SO2—； 或其药学上可接受的盐、溶剂或水合物； 但是，公开的衍生物式(I)不包括2-(4-乙基苯基)-4-吗啡啶基乙醇或4-[4-(2-羟乙基)-2-吗啡啶基]苯乙腈或其药学上可接受的盐、溶剂或水合物。 本公开的化合物具有对S1P受体的亲和力，并可用于治疗、缓解或预防S1P受体介导的疾病和症状。