6-(benzo[b]thien-2-yl)-1-bromohexane | 120772-89-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 6-(benzo[b]thien-2-yl)-1-bromohexane
• 英文别名: 2-(6-bromohexyl)-1-benzothiophene
• CAS: 120772-89-6
• 化学式: C₁₄H₁₇BrS
• 分子量: 297.259
• InChiKey: NZWKDCOAUXRHBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(benzo[b]thien-2-yl)-1-bromohexane 在 rose bengal 氧气 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-(1-acetoxy-7-benzo[b]thien-2-yl-heptyl)-5-hydroxy-2(5H)-furanone
  参考文献：
  名称：

  Singlet oxygen oxidation of substituted furans to 5-hydroxy-2(5H)-furanone

  摘要：

  The conditions for the regiospecific singlet oxygen oxidation of various 2,4-disubstituted furans 9 to 4-substituted-2 (5H)-furanones 3 are developed. The presence of a C-2 substituent (e.g., trimethylsilyl, tert-butyldimethylsilyl, or tributylstannyl) in 9 is an absolute requirement for the formation of the 4-substituted-5-hydroxy-2(5H)-furanone regioisomer 3. When the C-2 substituent is triethylsilyl (TES) or TBDMS, however, apart from 3, the corresponding 5-trialkylsiloxy derivative 11 is also isolated in a significant amount. These silyl acetals are unexpectedly stable but can be hydrolyzed back to 3 on stirring with dilute acid. The formation of silyl acetals, to our knowledge, has never been reported in the singlet oxygen oxidation of (trialkylsilyl)furan. A plausible mechanism for their formation is proposed. The presence of a catalytic amount of water in the oxidation of 2-(trialkylsilyl)-4-substituted-furans not only eliminates the formation of the silyl acetals but also speeds up the rate of the oxidation process. Moreover, the oxidation can then be carried out at 0-degrees-C instead of at -78-degrees-C. Oxidation of 2-(1-hydroxyalkyl)-4-substituted-furans in the absence of a reducing agent gives little or no sign of 2,5-disubstituted-6-hydroxy-3(2H)-pyranone 23 but instead 26 selectively. Thus, the (1-hydroxy)alkyl group can be utilized as the trialkylsilyl or trialkylstannyl group in dictating the regioselectivity in the singlet oxygen oxidation of substituted furans.

  DOI：

  10.1021/jo00025a012
• 作为产物：
  描述：

  1,6-二溴己烷 、 乙醚 、 苯并噻吩 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 6-(benzo[b]thien-2-yl)-1-bromohexane
  参考文献：
  名称：

  Anti-inflammatory furanones

  摘要：

  新的具有抗炎、免疫抑制和抗增殖活性的5-羟基-2-呋喃酮化合物对治疗牛皮癣和调节钙稳态具有用处。

  公开号：

  US05134128A1

文献信息

• Anti-inflammatory furanone compounds
  申请人：ALLERGAN, INC.

  公开号：EP0429287A2

  公开（公告）日：1991-05-29

  The invention relates to compounds of the formula (A): wherein R₁ is C₁-C₁₇ alkyl or alkenyl having 1-5 unconjugated double bonds, carbocyclic aryl (C₁-C₁₇ alkyl or alkenyl having 1-5 unconjugated double bonds), or heteroaryl (C₁-C₁₇ alkyl or alkenyl having 1-5 unconjugated double bonds), cyclohexyl or cyclohexyl-(C₁-C₁₇ alkyl or alkenyl having 1-5 unconjugated double bonds); X is R₁ being linked to X through bond a; R₂ is hydrogen or C₁-C₄ alkyl; and R₃ is hydrogen or C₁-C₁₂ alkanoyl. Such compounds have anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis. A compound of the invention is 4-[3,6-dihydro-6-hydroxy-5-(3-phenylpropyl)-2H-pyran-2-yl]-5-hydroxy-2-(5H)-furanone.

  本发明涉及式 (A) 的化合物： 其中 R₁ 是具有 1-5 个未共轭双键的 C₁-C₁₇ 烷基或烯基、碳环芳基（具有 1-5 个未共轭双键的 C₁-C₁₇ 烷基或烯基）、或杂芳基（具有 1-5 个未共轭双键的 C₁-C₁₇ 烷基或烯基）、环己基或环己基-（具有 1-5 个未共轭双键的 C₁-C₁₇ 烷基或烯基）； X 是 R₁ 通过键 a 与 X 连接； R₂ 是氢或 C₁-C₄ 烷基；以及 R₃ 是氢或 C₁-C₁₂ 烷酰基。 此类化合物具有抗炎、免疫抑制和抗增殖活性，可用于治疗牛皮癣和调节钙平衡。本发明的一种化合物是 4-[3,6-二氢-6-羟基-5-(3-苯基丙基)-2H-吡喃-2-基]-5-羟基-2-(5H)-呋喃酮。
• US5112853A
  申请人：——

  公开号：US5112853A

  公开（公告）日：1992-05-12
• US5134128A
  申请人：——

  公开号：US5134128A

  公开（公告）日：1992-07-28
• US5258400A
  申请人：——

  公开号：US5258400A

  公开（公告）日：1993-11-02
• Anti-inflammatory furanones
  申请人：Allergan, Inc.

  公开号：US05134128A1

  公开（公告）日：1992-07-28

  New 5-hydroxy-2-furanone compounds having anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.

  新的具有抗炎、免疫抑制和抗增殖活性的5-羟基-2-呋喃酮化合物对治疗牛皮癣和调节钙稳态具有用处。