((E)-5-bromo-2-methyl-pent-2-enyloxy)-tert-butyl-dimethyl-silane | 203321-78-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ((E)-5-bromo-2-methyl-pent-2-enyloxy)-tert-butyl-dimethyl-silane
• 英文别名: {[(2E)-5-Bromo-2-methyl-2-pentenyl]oxy}(tert-butyl)dimethylsilane；[(E)-5-bromo-2-methylpent-2-enoxy]-tert-butyl-dimethylsilane
• CAS: 203321-78-2
• 化学式: C₁₂H₂₅BrOSi
• 分子量: 293.319
• InChiKey: HVTFXKDYNKRKQW-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-((1R,2R)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-2-o-tolylacetamide 、 ((E)-5-bromo-2-methyl-pent-2-enyloxy)-tert-butyl-dimethyl-silane 在 正丁基锂 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.33h， 以68%的产率得到(E)-(R)-7-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-o-tolyl-hept-5-enoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide
  参考文献：
  名称：

  From Silphinenes to Penifulvins: A Biomimetic Approach to Penifulvins B and C

  摘要：

  The biomimetic total synthesis of penifulvins B and C uses a meta-photocycloaddition as a key step which gives rapid access to the fenestrane-type carboskeleton with control of an onring quaternary stereocenter. The route Is concise, stereocontrolled, scaleable, and flexibile and requires only one protecting group.

  DOI：

  10.1021/ol902594b
• 作为产物：
  描述：

  (E)-5-bromo-2-methylpent-2-en-1-ol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以98%的产率得到((E)-5-bromo-2-methyl-pent-2-enyloxy)-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  From Silphinenes to Penifulvins: A Biomimetic Approach to Penifulvins B and C

  摘要：

  The biomimetic total synthesis of penifulvins B and C uses a meta-photocycloaddition as a key step which gives rapid access to the fenestrane-type carboskeleton with control of an onring quaternary stereocenter. The route Is concise, stereocontrolled, scaleable, and flexibile and requires only one protecting group.

  DOI：

  10.1021/ol902594b

文献信息

• From Silphinenes to Penifulvins: A Biomimetic Approach to Penifulvins B and C
  作者：Tanja Gaich、Johann Mulzer

  DOI：10.1021/ol902594b

  日期：2010.1.15

  The biomimetic total synthesis of penifulvins B and C uses a meta-photocycloaddition as a key step which gives rapid access to the fenestrane-type carboskeleton with control of an onring quaternary stereocenter. The route Is concise, stereocontrolled, scaleable, and flexibile and requires only one protecting group.