(1R,5R,6R)-1-allyl-3-bromo-4-((tert-butyldimethylsilyloxy)-methyl)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-one | 1360808-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5R,6R)-1-allyl-3-bromo-4-((tert-butyldimethylsilyloxy)-methyl)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
• 英文别名: (1R,5R,6R)-3-bromo-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-hydroxy-1-prop-2-enyl-7-oxabicyclo[4.1.0]hept-3-en-2-one
• CAS: 1360808-53-2
• 化学式: C₁₆H₂₅BrO₄Si
• 分子量: 389.362
• InChiKey: FBFZBXIJVRZXDR-XPKDYRNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,5R,6R)-1-allyl-3-bromo-4-((tert-butyldimethylsilyloxy)-methyl)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-one 在 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.55h， 生成 (E)-tert-butyl 4-((1R,5R,6R)-3-bromo-4-((tert-butyldimethylsilyloxy)methyl)-5-hydroxy-2-oxo-7-oxabicyclo-[4.1.0]hept-3-en-1-yl)-2-methylbut-2-enoate
  参考文献：
  名称：

  Total Synthsis of (+)-Ambuic Acid: α-Bromination with 1,2-Dibromotetrachloroethane

  摘要：

  Total synthesis of (+)-ambuic acid has been accomplished from the readily available stereocontrolled Diels-Alder adduct of cyclopentadiene and iodo-1,4-benzoquinone monoketal through an efficient series of steps. A new method for the highly commendable synthesis of alpha-brominated Diels-Alder adduct is described.

  DOI：

  10.1021/jo202357s
• 作为产物：
  描述：

  (1'R,4'S,4'aS,6'S,7'R,8'aR)-7'-allyl-1',4',4'a,8'a-tetrahydro-(1',4'-methanonaphtho-6',7'-epoxy)-5',8'-dione 在 咪唑 、 二苯醚 、 1,2-二溴四氯乙烷 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.5h， 生成 (1R,5R,6R)-1-allyl-3-bromo-4-((tert-butyldimethylsilyloxy)-methyl)-5-hydroxy-7-oxabicyclo[4.1.0]hept-3-en-2-one
  参考文献：
  名称：

  Total Synthsis of (+)-Ambuic Acid: α-Bromination with 1,2-Dibromotetrachloroethane

  摘要：

  Total synthesis of (+)-ambuic acid has been accomplished from the readily available stereocontrolled Diels-Alder adduct of cyclopentadiene and iodo-1,4-benzoquinone monoketal through an efficient series of steps. A new method for the highly commendable synthesis of alpha-brominated Diels-Alder adduct is described.

  DOI：

  10.1021/jo202357s

文献信息

• Total Synthsis of (+)-Ambuic Acid: α-Bromination with 1,2-Dibromotetrachloroethane
  作者：Sun Hee Jung、Geum-Sook Hwang、Sung Il Lee、Do Hyun Ryu

  DOI：10.1021/jo202357s

  日期：2012.3.2

  Total synthesis of (+)-ambuic acid has been accomplished from the readily available stereocontrolled Diels-Alder adduct of cyclopentadiene and iodo-1,4-benzoquinone monoketal through an efficient series of steps. A new method for the highly commendable synthesis of alpha-brominated Diels-Alder adduct is described.