(6aS,9R,10aR,11aS)-1-Hydroxy-6,6,9-trimethyloctahydro-6H-[1,4]oxazino[3,4-b][1,3]benzoxazin-3(4H)-one | 1277183-25-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6aS,9R,10aR,11aS)-1-Hydroxy-6,6,9-trimethyloctahydro-6H-[1,4]oxazino[3,4-b][1,3]benzoxazin-3(4H)-one
• 英文别名: (3S,6R,8R,10S)-11-hydroxy-2,2,6-trimethyl-9,12-dioxa-1-azatricyclo[8.4.0.03,8]tetradecan-13-one
• CAS: 1277183-25-1
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: VTOJTOGCIBREIJ-UCCBVEOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6aS,9R,10aR,11aS)-1-Hydroxy-6,6,9-trimethyloctahydro-6H-[1,4]oxazino[3,4-b][1,3]benzoxazin-3(4H)-one 在 四甲基乙二胺 、 氢气 、 nickel(II) acetate tetrahydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 0.25h， 生成 (1S,6aS,9R,10aR,11aS)-6,6,9-trimethyl-1-[(1Z)-4-phenylbut-1-en-1-yl]octahydro-6H-[1,4]oxazino[3,4-b][1,3]benzoxazin-3(4H)-one
  参考文献：
  名称：

  A Stereoselective Approach to γ-Functionalized Carbonyls Exploiting the Cu-Promoted S_N2′ Reaction

  摘要：

  While several efficient processes exist to effect the stereoselective creation of carbon-carbon bonds in the alpha- and beta-position of carbonyls, functionalization of the gamma-position is much more challenging. We disclose an alternative methodology exploiting the Cu-promoted S(N)2' reaction to achieve the addition of various nucleophiles upon the allylic lactones 5a-d which lead to the generation of the desired y-functionalized alpha,beta-unsaturated aldehydes 6 following in situ hydrolysis.

  DOI：

  10.1021/jo102213d
• 作为产物：
  描述：

  (-)-aminomenthol 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 (6aS,9R,10aR,11aS)-1-Hydroxy-6,6,9-trimethyloctahydro-6H-[1,4]oxazino[3,4-b][1,3]benzoxazin-3(4H)-one
  参考文献：
  名称：

  A Stereoselective Approach to γ-Functionalized Carbonyls Exploiting the Cu-Promoted S_N2′ Reaction

  摘要：

  While several efficient processes exist to effect the stereoselective creation of carbon-carbon bonds in the alpha- and beta-position of carbonyls, functionalization of the gamma-position is much more challenging. We disclose an alternative methodology exploiting the Cu-promoted S(N)2' reaction to achieve the addition of various nucleophiles upon the allylic lactones 5a-d which lead to the generation of the desired y-functionalized alpha,beta-unsaturated aldehydes 6 following in situ hydrolysis.

  DOI：

  10.1021/jo102213d

文献信息

• A Stereoselective Approach to γ-Functionalized Carbonyls Exploiting the Cu-Promoted S_N2′ Reaction
  作者：Eric Bond、Anne-Marie Beausoleil、Jennifer Howell、Alicia Wong、Joël Robichaud

  DOI：10.1021/jo102213d

  日期：2011.4.15

  While several efficient processes exist to effect the stereoselective creation of carbon-carbon bonds in the alpha- and beta-position of carbonyls, functionalization of the gamma-position is much more challenging. We disclose an alternative methodology exploiting the Cu-promoted S(N)2' reaction to achieve the addition of various nucleophiles upon the allylic lactones 5a-d which lead to the generation of the desired y-functionalized alpha,beta-unsaturated aldehydes 6 following in situ hydrolysis.