(3R*,4S*)-4-hydroxylamino-3-methyl-4-phenyl-1-butene | 105251-37-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R*,4S*)-4-hydroxylamino-3-methyl-4-phenyl-1-butene
• 英文别名: N-(2-methyl-1-phenylbut-3-enyl)hydroxylamine；N-[(1R,2S)-2-methyl-1-phenylbut-3-enyl]hydroxylamine
• CAS: 105251-37-4
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: YFCXAZRGAIDUFG-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R*,4S*)-4-hydroxylamino-3-methyl-4-phenyl-1-butene 、 特戊醛 在 camphor-10-sulfonic acid 作用下， 以 异丙醇 为溶剂， 反应 60.0h， 以86%的产率得到(R,5E)-N-benzylidene-2,2-dimethylhept-5-en-3-amine N-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
• 作为产物：
  描述：

  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 在 lithium hydroxide 、 盐酸羟胺 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以96%的产率得到(3R*,4S*)-4-hydroxylamino-3-methyl-4-phenyl-1-butene
  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

• Hoffmann, Reinhard W.; Endesfelder, Andreas, Liebigs Annalen der Chemie, 1987, p. 215 - 220
  作者：Hoffmann, Reinhard W.、Endesfelder, Andreas

  DOI：——

  日期：——
• 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.