cis-1-(N-tert-butoxycarbonyl-N-hydroxyamino)-2-neopentoxycyclopent-3-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1-(N-tert-butoxycarbonyl-N-hydroxyamino)-2-neopentoxycyclopent-3-ene
• 英文别名: tert-butyl N-[(1S,2R)-2-(2,2-dimethylpropoxy)cyclopent-3-en-1-yl]-N-hydroxycarbamate
• 化学式: C₁₅H₂₇NO₄
• 分子量: 285.384
• InChiKey: NUEMLVACVJBCPM-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  新戊醇 、 2-oxa-3-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylic acid tert-butyl ester 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以35%的产率得到cis-1-(N-tert-butoxycarbonyl-N-hydroxyamino)-2-neopentoxycyclopent-3-ene
  参考文献：
  名称：

  Ruthenium-Catalyzed Nucleophilic Ring-Opening Reactions of a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene with Alcohols

  摘要：

  Ruthenium-catalyzed nucleophilic ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols were investigated. When a neutral ruthenium(II) catalyst, Cp*RuCl(COD), was used in MeOH, the trans-1,2-ring opened product was formed as the only regio- and stereoisomer. On the other hand, When a cationic ruthenium(II) catalyst, [CpRu(CH3CN)(3)]PF6, was used in MeOH, the cis-1,2-ring opened product was formed exclusively. Moderate to excellent stereoselectivity (70:30 to 100:0) was observed with various alcohols.

  DOI：

  10.1021/ol900454q

文献信息

• Ruthenium-Catalyzed Nucleophilic Ring-Opening Reactions of a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene with Alcohols
  作者：Ben P. Machin、Jennifer Howell、Jérémie Mandel、Nicolas Blanchard、William Tam

  DOI：10.1021/ol900454q

  日期：2009.5.21

  Ruthenium-catalyzed nucleophilic ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols were investigated. When a neutral ruthenium(II) catalyst, Cp*RuCl(COD), was used in MeOH, the trans-1,2-ring opened product was formed as the only regio- and stereoisomer. On the other hand, When a cationic ruthenium(II) catalyst, [CpRu(CH3CN)(3)]PF6, was used in MeOH, the cis-1,2-ring opened product was formed exclusively. Moderate to excellent stereoselectivity (70:30 to 100:0) was observed with various alcohols.