[(1'R,2'S,6'S)-4'-bromospiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-yl]oxy-tert-butyl-dimethylsilane | 620949-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(1'R,2'S,6'S)-4'-bromospiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-yl]oxy-tert-butyl-dimethylsilane
• CAS: 620949-83-9
• 化学式: C₁₅H₂₅BrO₄Si
• 分子量: 377.351
• InChiKey: HYUVZEDHGBUSLC-DRZSPHRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1'R,2'S,6'S)-4'-bromospiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-yl]oxy-tert-butyl-dimethylsilane 在 platinum(IV) oxide 、 tris(dibenzylideneacetone)dipalladium (0) 三苯胂 、 (antracen-9-yl)CH₂CH₂C(O)NH-resin 、 氢气 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 52.0h， 生成 (3aR,5aR,8R,9S,9aS,9bS)-2-ethyl-octahydro-8,9-dihydroxy-2H-benzo[e]isoindole-1,3,6(9bH)-trione
  参考文献：
  名称：

  Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds

  摘要：

  We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereocontrolled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.

  DOI：

  10.1021/jo050956y
• 作为产物：
  描述：

  (1'R,6'S)-4'-bromospiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-one 在 咪唑 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(1'R,2'S,6'S)-4'-bromospiro[1,3-dioxane-2,5'-7-oxabicyclo[4.1.0]hept-3-ene]-2'-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds

  摘要：

  We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereocontrolled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.

  DOI：

  10.1021/jo050956y

文献信息

• 一种Scabrosins/Ambewelamides骨架结构的合成方法
  申请人：重庆大学

  公开号：CN111423465A

  公开（公告）日：2020-07-17

  本发明涉及一种Scabrosins/Ambewelamides骨架结构的合成方法。该合成方法利用Negishi偶联反应、还原胺化反应、不对称环氧化反应、Mitsunobu反应、分子内亲核取代反应完成了Scabrosins/Ambewelamides骨架结构的构建。该合成方法操作简单、反应条件温和、成本低、收率高，为该天然产物的全合成打下了基础。
• Convergent Synthesis of a Complex Oxime Library Using Chemical Domain Shuffling
  作者：Shun Su、Dayle E. Acquilano、Jeevanandam Arumugasamy、Aaron B. Beeler、Erin L. Eastwood、Joshua R. Giguere、Ping Lan、Xiaoguang Lei、Geanna K. Min、Adam R. Yeager、Ya Zhou、James S. Panek、John K. Snyder、Scott E. Schaus、John A. Porco

  DOI：10.1021/ol051023r

  日期：2005.6.1

  yThe synthesis of a complex hybrid oxime library is reported utilizing convergent ligation of alkoxyamine and carbonyl monomers via "chemical domain shuffling". Initial biological screening of the library against human small cell lung carcinoma (A549) cells led to the identification of a novel hybrid dimer in contrast to the corresponding monomeric compounds which were found to be inactive.
• Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds
  作者：Xiaoguang Lei、Nava Zaarur、Michael Y. Sherman、John A. Porco

  DOI：10.1021/jo050956y

  日期：2005.8.1

  We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereocontrolled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.