[8-(2,3,6-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-7-yl]methanol | 944952-37-8

• 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: [8-(2,3,6-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-7-yl]methanol
• CAS: 944952-37-8
• 化学式: C₁₅H₁₅F₃O₃
• 分子量: 300.278
• InChiKey: YORSWQHHASCZJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [8-(2,3,6-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-7-yl]methanol 在 potassium tert-butylate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 3',6'-Difluorospiro[1,3-dioxolane-2,12'-8,15-dioxatetracyclo[8.4.1.01,10.02,7]pentadeca-2,4,6-triene]
  参考文献：
  名称：

  Stereoselective synthesis of C-6 hydroxy tricyclic sulfone as a γ-secretase inhibitor

  摘要：

  The synthesis of a C-6 hydroxy tricyclic sulfone was described with two key reactions: the Suzuki coupling and the regioselective and stereoselective cis ring opening of the epoxide. Overall, the 14-step synthesis was achieved in 2.1% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.091
• 作为产物：
  描述：

  8-氧代-1,4-二噁螺[4.5]癸烷-7-羧酸甲酯 在 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 sodium hydride 、 lithium chloride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 26.42h， 生成 [8-(2,3,6-Trifluorophenyl)-1,4-dioxaspiro[4.5]dec-7-en-7-yl]methanol
  参考文献：
  名称：

  Stereoselective synthesis of C-6 hydroxy tricyclic sulfone as a γ-secretase inhibitor

  摘要：

  The synthesis of a C-6 hydroxy tricyclic sulfone was described with two key reactions: the Suzuki coupling and the regioselective and stereoselective cis ring opening of the epoxide. Overall, the 14-step synthesis was achieved in 2.1% yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.091

文献信息

• Synthesis and SAR study of tricyclic sulfones as γ-secretase inhibitors: C-6 and C-8 positions
  作者：Jing Su、Haiqun Tang、Brian A. McKittrick、Ruo Xu、John W. Clader、William J. Greenlee、Lynn Hyde、Lili Zhang

  DOI：10.1016/j.bmcl.2011.03.094

  日期：2011.6

  SAR exploration at C-6 and C-8 positions of the tricyclic sulfone series was carried out. Several functional groups were found to be well tolerated at C-6 and C-8 positions. Selective combination of C-6 and C-8 modification resulted in new tricyclic sulfone analogs with efficacy in in vivo mouse A beta(40) lowering model. (C) 2011 Elsevier Ltd. All rights reserved.