5-(4,4,4-Trifluoro-butoxy)-indan-1,2,3-trione | 521079-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4,4,4-Trifluoro-butoxy)-indan-1,2,3-trione
• 英文别名: 5-(4,4,4-trifluorobutoxy)indene-1,2,3-trione
• CAS: 521079-64-1
• 化学式: C₁₃H₉F₃O₄
• 分子量: 286.207
• InChiKey: SQGTVISHBDLHBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(4,4,4-Trifluoro-butoxy)-indan-1,2,3-trione 在 一水合肼 作用下， 以 溶剂黄146 为溶剂， 反应 26.0h， 生成 3-methyl-8-(4,4,4-trifluoro-butoxy)indeno[1,2-c]pyridazin-5-one
  参考文献：
  名称：

  Rational approaches towards reversible inhibition of type B monoamine oxidase. Design and evaluation of a novel 5H-Indeno[1,2-c]pyridazin-5-one derivative

  摘要：

  The stereoelectronic properties of several potent reversible monoamine oxidase B (MAO-B) inhibitors were studied with a view to develop a pharmacophore model for reversible MAO-B inhibition. This study suggested that important specific H-bond and hydrophobic interactions are required for potent and selective MAO-B inhibition. These requirements were applied in the design and synthesis of a novel reversible and selective MAO-B inhibitor, 3-methyl-8-(4,4,4-trifluoro-butoxy)indeno[1,2-c]pyridazin5-one, that is ca. 7000 times more selective as an inhibitor for MAO-B than for MAO-A, with Ki(MAO-B) in the low nanomolar range. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00838-7
• 作为产物：
  描述：

  5-甲氧基-1-茚酮 在 selenium(IV) oxide 、 氢溴酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 9.5h， 生成 5-(4,4,4-Trifluoro-butoxy)-indan-1,2,3-trione
  参考文献：
  名称：

  Rational approaches towards reversible inhibition of type B monoamine oxidase. Design and evaluation of a novel 5H-Indeno[1,2-c]pyridazin-5-one derivative

  摘要：

  The stereoelectronic properties of several potent reversible monoamine oxidase B (MAO-B) inhibitors were studied with a view to develop a pharmacophore model for reversible MAO-B inhibition. This study suggested that important specific H-bond and hydrophobic interactions are required for potent and selective MAO-B inhibition. These requirements were applied in the design and synthesis of a novel reversible and selective MAO-B inhibitor, 3-methyl-8-(4,4,4-trifluoro-butoxy)indeno[1,2-c]pyridazin5-one, that is ca. 7000 times more selective as an inhibitor for MAO-B than for MAO-A, with Ki(MAO-B) in the low nanomolar range. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00838-7

文献信息

• Rational approaches towards reversible inhibition of type B monoamine oxidase. Design and evaluation of a novel 5H-Indeno[1,2-c]pyridazin-5-one derivative
  作者：Frédéric Ooms、Raphaël Frédérick、François Durant、Jacobus P Petzer、Neal Castagnoli、Cornelis J Van der Schyf、Johan Wouters

  DOI：10.1016/s0960-894x(02)00838-7

  日期：2003.1

  The stereoelectronic properties of several potent reversible monoamine oxidase B (MAO-B) inhibitors were studied with a view to develop a pharmacophore model for reversible MAO-B inhibition. This study suggested that important specific H-bond and hydrophobic interactions are required for potent and selective MAO-B inhibition. These requirements were applied in the design and synthesis of a novel reversible and selective MAO-B inhibitor, 3-methyl-8-(4,4,4-trifluoro-butoxy)indeno[1,2-c]pyridazin5-one, that is ca. 7000 times more selective as an inhibitor for MAO-B than for MAO-A, with Ki(MAO-B) in the low nanomolar range. (C) 2002 Elsevier Science Ltd. All rights reserved.