1,4-difluoro-2-({[4-(trifluoromethyl)phenyl]sulfonyl}methyl)benzene | 471905-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-difluoro-2-({[4-(trifluoromethyl)phenyl]sulfonyl}methyl)benzene
• 英文别名: 1,4-Difluoro-2-[[4-(trifluoromethyl)phenyl]sulfonylmethyl]benzene
• CAS: 471905-57-4
• 化学式: C₁₄H₉F₅O₂S
• 分子量: 336.282
• InChiKey: KFOAGQCJXWSYQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,4-difluoro-2-({[4-(trifluoromethyl)phenyl]sulfonyl}methyl)benzene 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.75h， 生成 2-(3-(2,5-difluorophenyl)-3-{[4-(trifluoromethyl)phenyl]sulfonyl}hex-5-en-1-yl)-1,3-dioxolane
  参考文献：
  名称：

  Practical Asymmetric Synthesis of a γ-Secretase Inhibitor Exploiting Substrate-Controlled Intramolecular Nitrile Oxide−Olefin Cycloaddition

  摘要：

  A practical asymmetric synthesis of the gamma-secretase inhibitor (-)-1 is described. As the key transformation, a highly diastereoselective intramolecular nitrile oxide cycloaddition forms the hexahydrobenzisoxazole core of 3 in four operations. Other aspects of the route include a highly stereoselective reduction of an isoxazole to form a cis-gamma-amino alcohol, an efficient chemical resolution, a dianion cyclization to construct a sultam ring, and the alpha-alkylation of a sultam with excellent diastereoselectivity. In each instance, the relative stereochemistry was evolved by way of substrate-based induction with >= 96% ds. Kilogram quantities of the targeted drug candidate (-)-1 were obtained, without recourse to chromatography, by way of 10 isolated intermediates and in 13% overall yield.

  DOI：

  10.1021/jo060033i
• 作为产物：
  描述：

  4-(三氟甲基)苯硫酚 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 22.5h， 生成 1,4-difluoro-2-({[4-(trifluoromethyl)phenyl]sulfonyl}methyl)benzene
  参考文献：
  名称：

  Practical Asymmetric Synthesis of a γ-Secretase Inhibitor Exploiting Substrate-Controlled Intramolecular Nitrile Oxide−Olefin Cycloaddition

  摘要：

  A practical asymmetric synthesis of the gamma-secretase inhibitor (-)-1 is described. As the key transformation, a highly diastereoselective intramolecular nitrile oxide cycloaddition forms the hexahydrobenzisoxazole core of 3 in four operations. Other aspects of the route include a highly stereoselective reduction of an isoxazole to form a cis-gamma-amino alcohol, an efficient chemical resolution, a dianion cyclization to construct a sultam ring, and the alpha-alkylation of a sultam with excellent diastereoselectivity. In each instance, the relative stereochemistry was evolved by way of substrate-based induction with >= 96% ds. Kilogram quantities of the targeted drug candidate (-)-1 were obtained, without recourse to chromatography, by way of 10 isolated intermediates and in 13% overall yield.

  DOI：

  10.1021/jo060033i

文献信息

• Sulphones which modulate the action of gammasecretase
  申请人：Castro Pineiro Luis Jose

  公开号：US20070213329A1

  公开（公告）日：2007-09-13

  Novel sulphones of Formula I are disclosed: wherein A completes a 4-7 membered ring optionally comprising up to two heteroatoms. The compounds modulate the action of γ-secretase and are therefore useful in the treatment or prevention of Alzheimer's disease.

  公开了一种化学式为I的新型磺酰类化合物：其中A形成一个4-7环，可选地包含最多两个杂原子。这些化合物调节γ-分泌酶的作用，因此可用于治疗或预防阿尔茨海默病。
• Novel cyclohexyl sulphones
  申请人：Churcher Ian

  公开号：US20080045533A1

  公开（公告）日：2008-02-21

  Novel sulphones of formula I are disclosed: The compounds modulate the processing of amyloid precursor protein by gamma-secretase, and hence are useful in the treatment or prevention of Alzheimer's disease.

  公开了化学式为I的新型磺酰化合物：该化合物通过调节γ-分泌酶对淀粉样前体蛋白的处理，因此可用于治疗或预防阿尔茨海默病。
• Sulphones which modulate the action of gamma secretase
  申请人：Castro Pineiro Jose Luis

  公开号：US20090131419A1

  公开（公告）日：2009-05-21

  Disclosed are sulphones which modulate the action of gamma-secretase. The compounds are useful in the treatment or prevention of Alzheimer's disease.

  公开了可以调节γ-分泌酶作用的磺酰化合物。这些化合物对治疗或预防阿尔茨海默病有用。
• CYCLOHEXYL SULPHONES FOR TREATMENT OF CANCER
  申请人：Lewis Huw David

  公开号：US20100267801A1

  公开（公告）日：2010-10-21

  Sulphones of formula (I) are disclosed for use in treatment of cancer.
• US7304094B2
  申请人：——

  公开号：US7304094B2

  公开（公告）日：2007-12-04