N-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-phenylmethanimine oxide | 114987-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-phenylmethanimine oxide
• CAS: 114987-90-5
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: OUHFCMIVIRIILV-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酰溴 、 N-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-phenylmethanimine oxide 、 三丁基(1-甲基烯丙基)锡 以 二氯甲烷 为溶剂， 反应 12.0h， 以76%的产率得到O-acetyl-N-((3aS,4S,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-N-((1R,2S)-2-methyl-1-phenylbut-3-en-1-yl)hydroxylamine
  参考文献：
  名称：

  Homoallyllic Nitrone Isomerization: Convenient Enantioselective Synthesis of Homoallylic Nitrones and Homoallylic Hydroxylamines

  摘要：

  An alpha-regioselective synthesis of homoallylic nitrones from aldehydes is reported on the basis of [3,3]-sigmatropic rearrangement. The products are obtained in up to 99% enantioselectivity and up to 80% yield under environmentally benign and mild reaction conditions.

  DOI：

  10.1021/ol800925v
• 作为产物：
  描述：

  苯甲醛 、 2,3:5,6-di-O-isopropylidene-D-mannose oxime 以99%的产率得到N-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-1-phenylmethanimine oxide
  参考文献：
  名称：

  Homoallyllic Nitrone Isomerization: Convenient Enantioselective Synthesis of Homoallylic Nitrones and Homoallylic Hydroxylamines

  摘要：

  An alpha-regioselective synthesis of homoallylic nitrones from aldehydes is reported on the basis of [3,3]-sigmatropic rearrangement. The products are obtained in up to 99% enantioselectivity and up to 80% yield under environmentally benign and mild reaction conditions.

  DOI：

  10.1021/ol800925v

文献信息

• Homoallyllic Nitrone Isomerization: Convenient Enantioselective Synthesis of Homoallylic Nitrones and Homoallylic Hydroxylamines
  作者：Hin-Soon Cheng、Ai-Hua Seow、Teck-Peng Loh

  DOI：10.1021/ol800925v

  日期：2008.7.3

  An alpha-regioselective synthesis of homoallylic nitrones from aldehydes is reported on the basis of [3,3]-sigmatropic rearrangement. The products are obtained in up to 99% enantioselectivity and up to 80% yield under environmentally benign and mild reaction conditions.