2-(5-溴-2-甲氧基苯氧基)环戊烷-1-酮 | 185244-57-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(5-溴-2-甲氧基苯氧基)环戊烷-1-酮
• 英文名称: 2-(5-bromo-2-methoxyphenoxy)cyclopentanone
• 英文别名: 4-Methoxy-3-(2-oxocyclopentyloxy)bromobenzene；4-Bromo-2-(2-oxocyclopentyloxy)anisole；2-(5-bromo-2-methoxyphenoxy)cyclopentan-1-one
• CAS: 185244-57-9
• 化学式: C₁₂H₁₃BrO₃
• 分子量: 285.137
• InChiKey: BIUHJCSPFGAWEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-溴-2-甲氧基苯氧基)环戊烷-1-酮 在 Amberlyst 15 ion-exchange resin 、 potassium tert-butylate 、 sodium hydride 、 一水合肼 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 40.25h， 生成 cis-2-cycloheptyl-4-(2,3-dihydro-7-methoxybenzofuran-2-spiro-1'-cyclopentan-4-yl)-4a,5,8,8a-tetrahydro-2H-phthalazin-1-one
  参考文献：
  名称：

  Novel Selective PDE4 Inhibitors. 2. Synthesis and Structure−Activity Relationships of 4-Aryl-Substituted cis-Tetra- and cis-Hexahydrophthalazinones

  摘要：

  A series of 4-aryl-substituted cis-4a,5,8,8a-tetra- and cis-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-ones with high inhibitory activity toward cAMP-specific phosphodiesterase (PDE4) was synthesized. To study structure-activity relationships various substituents were introduced to the 2-, 3-, and 4-positions of the 4-phenyl ring. Substitution at the 4-position of the phenyl ring was restricted to a methoxy group, probably due to unfavorable steric interactions of larger groups with the binding site. The introduction of many alkoxy substituents including distinct ring systems and functional groups was allowed to the 3-position. It was found that in general the cis-4a,5,8,8a-tetrahydro-2H-phthalazin-1-ones are more potent than their hexahydrophthalic counterparts, the best activity residing in (4-imidazol-1-yl-phenoxy)butoxy analogue 16o (pIC(50) = 9.7).

  DOI：

  10.1021/jm010838c
• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲醛 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.5h， 生成 2-(5-溴-2-甲氧基苯氧基)环戊烷-1-酮
  参考文献：
  名称：

  Novel Selective PDE4 Inhibitors. 2. Synthesis and Structure−Activity Relationships of 4-Aryl-Substituted cis-Tetra- and cis-Hexahydrophthalazinones

  摘要：

  A series of 4-aryl-substituted cis-4a,5,8,8a-tetra- and cis-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-ones with high inhibitory activity toward cAMP-specific phosphodiesterase (PDE4) was synthesized. To study structure-activity relationships various substituents were introduced to the 2-, 3-, and 4-positions of the 4-phenyl ring. Substitution at the 4-position of the phenyl ring was restricted to a methoxy group, probably due to unfavorable steric interactions of larger groups with the binding site. The introduction of many alkoxy substituents including distinct ring systems and functional groups was allowed to the 3-position. It was found that in general the cis-4a,5,8,8a-tetrahydro-2H-phthalazin-1-ones are more potent than their hexahydrophthalic counterparts, the best activity residing in (4-imidazol-1-yl-phenoxy)butoxy analogue 16o (pIC(50) = 9.7).

  DOI：

  10.1021/jm010838c

文献信息

• Derivatives of benzofuran or benzodioxole
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US06514996B2

  公开（公告）日：2003-02-04

  An oxygen-containing heterocyclic compound represented by following Formula (I): wherein R1 and R2 independently represent hydrogen, lower alkyl, cyano, —(CH2)n—E1—CO—G1 (wherein E1 represents a bond, O, or NH; and G1 represents hydrogen, substituted or unsubstituted lower alkyl, OR6, or NR7R8; and n represents an integer of 0 to 4), or the like; R1 and R2 are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R2, and R11 or R13 described below are combined to form a single bond; R3 represents hydrogen, phenyl, or halogen; R4 represents hydroxy, lower alkoxy, or the like; A represents —C(R9)(R10)— or O; B represents O, NR11, —C(R12)(R13)—, or —C(R14)(R15)—C(R16)(R17)—; D represents (i) —C(R18)(R19)—X— (wherein X represents —C(R21)(R22)—, S, or NR23), (ii) —C(R19a)═Y— [Y represents —C(R24)—Z— (wherein Z represents CONH, CONHCH2, or a bond), or N], or (iii) a bond; and R5 represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or pharmaceutically acceptable salts thereof.

  根据您的要求，以下是该化学公式（I）的中文翻译： 一个含氧杂环化合物，由以下公式（I）表示：其中R1和R2独立代表氢、低级烷基、氰基、—(CH2)n—E1—CO—G1（其中E1代表一个键、O或NH；G1代表氢、取代或未取代的低级烷基、OR6或NR7R8；n代表0到4的整数），或类似物；R1和R2共同代表与相邻碳原子一起的饱和碳环；或者R2与下面描述的R11或R13结合形成一个单键；R3代表氢、苯基或卤素；R4代表羟基、低级烷氧基或类似物；A代表—C(R9)(R10)—或O；B代表O、NR11、—C(R12)(R13)—或—C(R14)(R15)—C(R16)(R17)—；D代表（i）—C(R18)(R19)—X—（其中X代表—C(R21)(R22)—、S或NR23）、（ii）—C(R19a)═Y— [Y代表—C(R24)—Z—（其中Z代表CONH、CONHCH2或一个键）或N]，或（iii）一个键；R5代表芳基、芳香杂环基、环烷基、吡啶-N-氧化物、氰基或低级烷氧基甲酸；或其药物可接受的盐。
• DERIVATIVES OF BENZOFURAN OR BENZODIOXOLE
  申请人：——

  公开号：US20020128290A1

  公开（公告）日：2002-09-12

  An oxygen-containing heterocyclic compound represented by following Formula (I): 1 wherein R 1 and R 2 independently represent hydrogen, lower alkyl, cyano, —(CH 2 ) n —E 1 —CO—G 1 (wherein E 1 represents a bond, O, or NH; and G 1 represents hydrogen, substituted or unsubstituted lower alkyl, OR 6 , or NR 7 R 8 ; and n represents an integer of 0 to 4), or the like; R 1 and R 2 are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R 2 , and R 11 or R 13 described below are combined to form a single bond; R 3 represents hydrogen, phenyl, or halogen; R 4 represents hydroxy, lower alkoxy, or the like; A represents —C(R 9 )(R 10 )— or O; B represents O, NR 11 , —C(R 12 )(R 13 )—, or —C(R 14 )(R 15 )—C(R 16 )(R 17 )—; D represents (i) —C(R 18 )(R 19 )—X— (wherein X represents —C(R 21 )(R 22 )—, S, or NR 23 ), (ii) —C(R 19a )═Y— [Y represents —C(R 24 )—Z— (wherein Z represents CONH, CONHCH 2 , or a bond), or N], or (iii) a bond; and R 5 represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or pharmaceutically acceptable salts thereof.

  以下是由下式（I）表示的含氧杂环化合物： 其中R1和R2独立地表示氢、较低的烷基、氰基、—（CH2）n—E1—CO—G1（其中E1表示键、O或NH；G1表示氢、取代或未取代的较低烷基、OR6或NR7R8；n表示0到4的整数），或类似物；R1和R2结合表示与相邻碳原子一起形成饱和碳环；或R2，以及下文描述的R11或R13结合形成单键；R3表示氢、苯基或卤素；R4表示羟基、较低的烷氧基或类似物；A表示—C（R9）（R10）—或O；B表示O、NR11、—C（R12）（R13）—或—C（R14）（R15）—C（R16）（R17）—；D表示（i）—C（R18）（R19）—X—（其中X表示—C（R21）（R22）—、S或NR23）、（ii）—C（R19a）═Y—［Y表示—C（R24）—Z—（其中Z表示CONH、CONHCH2或键），或N］，或（iii）键；R5表示芳基、芳香杂环基、环烷基、吡啶-N-氧化物、氰基或较低烷氧羰基；或其药学上可接受的盐。
• Substituted dihydrobenzofuran-based phosphodiesterase 4 inhibitors
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：US06054475A1

  公开（公告）日：2000-04-25

  Compounds of formula (I) ##STR1## and the salts of these compounds, are efficacious PDE (phosphodiesterase) inhibitors.

  式(I)的化合物及其盐是有效的PDE（磷酸二酯酶）抑制剂。
• Phenyldihydrobenzofuranes
  申请人：Byk Gulden Lomberg Chemische Fabrik GmbH

  公开号：US05902824A1

  公开（公告）日：1999-05-11

  Compounds of formula I are selective cyclic nucleotide phosphodiesterase (PDE) inhibitors (namely of type IV). They and pharmaceutical compositions in which they are active ingredients are useful as bronchial therapeutics, for elimination of erectile dysfunction and for treatment of disorders, particularly those of inflammatory nature. The compounds are distinguished by low toxicity, good enteral absorption (high bioavailability), a great therapeutic breadth and the absence of significant side effects.

  公式为I的化合物是选择性环核苷酸磷酸二酯酶（PDE）抑制剂（特别是类型IV）。它们和含有它们作为活性成分的药物组合物可用于支气管治疗、消除勃起功能障碍和治疗疾病，特别是炎症性疾病。这些化合物具有低毒性、良好的肠道吸收（高生物利用度）、广泛的治疗范围和无显著副作用的特点。
• Derivatives of benzofuran or benzodioxazole compounds
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US06716987B1

  公开（公告）日：2004-04-06

  An oxygen-containing heterocyclic compound represented by following Formula (I): wherein R1 and R2 independently represent hydrogen, lower alkyl, cyano, —(CH2)n—E1—CO—G1 (wherein E1 represents a bond, O, or NH; and G1 represents hydrogen, substituted or unsubstituted lower alkyl, OR6, or NR7R8; and n represents an integer of 0 to 4), or the like; R1 and R2 are combined to represent a saturated carbon ring together with a carbon atom adjacent thereto; or R2, and R11 or R13 described below are combined to form a single bond; R3 represents hydrogen, phenyl, or halogen; R4 represents hydroxy, lower alkoxy, or the like; A represents —C(R9)(R10)— or O; B represents O, NR11, —C(R12)(R13)—, or —C(R14)(R15)— C(R16)(R17)—; D represents (i) —C(R18)(R19)—X— (wherein X represents —C(R21)(R22)—, S, or NR23), (ii) —C(R19a)═Y— [Y represents —C(R24)—Z— (wherein Z represents CONH, CONHCH2, or a bond), or N], or (iii) a bond; and R5 represents aryl, an aromatic heterocyclic group, cycloalkyl, pyridine-N-oxide, cyano, or lower alkoxycarbonyl; or pharmaceutically acceptable salts thereof.

  以下式子所表示的含氧杂环化合物（I）：其中，R1和R2独立地表示氢、低碳烷基、氰基、—（CH2）n—E1—CO—G1（其中E1表示键、O或NH；G1表示氢、取代或未取代的低碳烷基、OR6或NR7R8；n表示0至4的整数），或类似物；R1和R2结合在一起，与相邻的碳原子一起表示饱和碳环；或R2和下面所述的R11或R13结合形成单键；R3表示氢、苯基或卤素；R4表示羟基、低碳基氧或类似物；A表示—C（R9）（R10）—或O；B表示O、NR11、—C（R12）（R13）—或—C（R14）（R15）—C（R16）（R17）—；D表示（i）—C（R18）（R19）—X—（其中X表示—C（R21）（R22）—、S或NR23），（ii）—C（R19a）═Y—[Y表示—C（R24）—Z—（其中Z表示CONH、CONHCH2或键），或N]，或（iii）键；R5表示芳基、芳杂环基、环烷基、吡啶-N-氧化物、氰基或低碳基氧羰基；或其药学上可接受的盐。