1-phenyl-N-[3-(4-bromophenyl)prop-2-ynylidene]methanamine oxide | 1022915-12-3

• 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: 1-phenyl-N-[3-(4-bromophenyl)prop-2-ynylidene]methanamine oxide
• CAS: 1022915-12-3
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: QUKNXIIXHXBACL-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-N-[3-(4-bromophenyl)prop-2-ynylidene]methanamine oxide 、 二苯锌 在 Dimethylzinc 、 (+)-二叔丁基 L-酒石酸 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 1.0h， 生成 (R)-N-benzyl-N-[3-(4-bromophenyl)-1-phenylprop-2-ynyl]hydroxylamine 、 (S)-N-benzyl-N-[3-(4-bromophenyl)-1-phenylprop-2-ynyl]hydroxylamine
  参考文献：
  名称：

  Asymmetric addition of phenylzinc reagents to C-alkynyl nitrones. Enantiomeric enhancement by a product-like additive

  摘要：

  Asymmetric addition of diphenylzinc to C-alkynyl nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (S)-N-(1-phenyl-3-substituted prop-2-ynyl)hydroxylamines. By the addition of a product-like additive, enantiomeric enhancement was observed. A mixed zinc reagent, PhZnMe, improved the enantioselection to afford hydroxylamines in up to 92% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.029
• 作为产物：
  描述：

  3-(4-bromophenyl)prop-2-ynal 、 N-苄基羟胺 在 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 生成 1-phenyl-N-[3-(4-bromophenyl)prop-2-ynylidene]methanamine oxide
  参考文献：
  名称：

  Asymmetric addition of phenylzinc reagents to C-alkynyl nitrones. Enantiomeric enhancement by a product-like additive

  摘要：

  Asymmetric addition of diphenylzinc to C-alkynyl nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (S)-N-(1-phenyl-3-substituted prop-2-ynyl)hydroxylamines. By the addition of a product-like additive, enantiomeric enhancement was observed. A mixed zinc reagent, PhZnMe, improved the enantioselection to afford hydroxylamines in up to 92% ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.01.029