N-benzyl-N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]hydroxylamine | 176909-81-2

• 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: N-benzyl-N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]hydroxylamine
• CAS: 176909-81-2
• 化学式: C₁₈H₁₈N₂OS
• 分子量: 310.42
• InChiKey: SBTUKVJOGAFTGQ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]hydroxylamine 在 titanium(III) chloride 作用下， 以 甲醇 为溶剂， 以66%的产率得到(S)-2-苯基-1-(噻唑-2-基)乙胺
  参考文献：
  名称：

  Enantioselective addition of Grignard reagents to a 2-thiazolyl nitrone

  摘要：

  The addition of organomagnesium compounds to the N-benzyl 2-thiazolyl nitrone 1 in the presence of various chiral additives and Lewis acids leads to hydroxylamines 2 in moderate to good enantiomeric excess (up to 74%); the reductive dehydroxylation of these compounds affords enantioenriched alpha-amino 2-alkylthiazoles 3 in good yields (76-66%). (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00060-2
• 作为产物：
  描述：

  苄基溴化镁 、 N-benzyl-α-(2-thiazolyl)nitrone 在 zinc dibromide 作用下， 生成 N-benzyl-N-[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]hydroxylamine 、 N-Benzyl-N-((R)-2-phenyl-1-thiazol-2-yl-ethyl)-hydroxylamine
  参考文献：
  名称：

  Enantioselective addition of Grignard reagents to a 2-thiazolyl nitrone

  摘要：

  The addition of organomagnesium compounds to the N-benzyl 2-thiazolyl nitrone 1 in the presence of various chiral additives and Lewis acids leads to hydroxylamines 2 in moderate to good enantiomeric excess (up to 74%); the reductive dehydroxylation of these compounds affords enantioenriched alpha-amino 2-alkylthiazoles 3 in good yields (76-66%). (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00060-2

文献信息

• Determination of the absolute configuration of α-amino-2-alkylthiazoles by circular dichroism
  作者：Francisco L. Merchán、Pedro Merino、Isabel Rojo、Tomás Tejero、Alessandro Dondoni

  DOI：10.1016/0957-4166(95)00286-x

  日期：1995.9

  Correlation between absolute configuration at the alpha-centre of the thiazole ring in the title compounds and the sign of their Cotton effect (CE) in the range 217-230 nm is reported.
• Enantioselective addition of Grignard reagents to a 2-thiazolyl nitrone
  作者：Francisco L. Merchán、Pedro Merino、Isabel Rojo、Tomas Tejero、Alessandro Dondoni

  DOI：10.1016/0957-4166(96)00060-2

  日期：1996.3

  The addition of organomagnesium compounds to the N-benzyl 2-thiazolyl nitrone 1 in the presence of various chiral additives and Lewis acids leads to hydroxylamines 2 in moderate to good enantiomeric excess (up to 74%); the reductive dehydroxylation of these compounds affords enantioenriched alpha-amino 2-alkylthiazoles 3 in good yields (76-66%). (C) 1996 Elsevier Science Ltd