3',6'-Difluorospiro[1,3-dioxolane-2,12'-8,15-dioxatetracyclo[8.4.1.01,10.02,7]pentadeca-2,4,6-triene] | 944952-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3',6'-Difluorospiro[1,3-dioxolane-2,12'-8,15-dioxatetracyclo[8.4.1.01,10.02,7]pentadeca-2,4,6-triene]
• CAS: 944952-39-0
• 化学式: C₁₅H₁₄F₂O₄
• 分子量: 296.271
• InChiKey: HMGPVCFTJHLGIY-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：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3',6'-Difluorospiro[1,3-dioxolane-2,12'-8,15-dioxatetracyclo[8.4.1.01,10.02,7]pentadeca-2,4,6-triene] 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 硼烷四氢呋喃络合物 、 水 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 83.58h， 生成
  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：

  (6'aR,10'aR)-10'a-(4-chlorophenyl)sulfanyl-1',4'-difluorospiro[1,3-dioxolane-2,8'-6,7,9,10-tetrahydrobenzo[c]chromene]-6'a-ol 在 potassium tert-butylate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 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

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.
• Stereoselective synthesis of C-6 hydroxy tricyclic sulfone as a γ-secretase inhibitor
  作者：Jing Su、Haiqun Tang、Brian A. McKittrick

  DOI：10.1016/j.tetlet.2011.04.091

  日期：2011.6

  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.