(S)-N1-(2-bromo-4-methylphenyl)-3-(tert-butyldimethylsilyloxy)-N2-[(R)-1-phenylethyl]propane-1,2-diamine | 1252060-08-4

• 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: (S)-N1-(2-bromo-4-methylphenyl)-3-(tert-butyldimethylsilyloxy)-N2-[(R)-1-phenylethyl]propane-1,2-diamine
• CAS: 1252060-08-4
• 化学式: C₂₄H₃₇BrN₂OSi
• 分子量: 477.56
• InChiKey: JLJACYIYSYVDKD-CTNGQTDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.29
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N1-(2-bromo-4-methylphenyl)-3-(tert-butyldimethylsilyloxy)-N2-[(R)-1-phenylethyl]propane-1,2-diamine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 以72%的产率得到(S)-2-[(tert-butyldimethylsilyloxy)methyl]-7-methyl-1-[(R)-1-phenylethyl]-1,2,3,4-tetrahydroquinoxaline
  参考文献：
  名称：

  An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines

  摘要：

  An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles was successfully achieved via Pd-catalyzed intramolecular C-N bond formation between the nitrogen originated from the aziridine and the halogen containing aromatic carbon. This reaction has a broad substrate scope to provide various enantiomerically pure (3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)methanols, 2-hydroxymethyl-1,2,3,4-tetrahydroquinolines and (1,2,3,4-tetrahydroquinoxalin-2-yl)methanols from common chiral aziridines in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.027
• 作为产物：
  描述：

  、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-N1-(2-bromo-4-methylphenyl)-3-(tert-butyldimethylsilyloxy)-N2-[(R)-1-phenylethyl]propane-1,2-diamine
  参考文献：
  名称：

  An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles from common chiral aziridines

  摘要：

  An efficient synthesis of enantiomerically pure aromatic-fused N-containing heterocycles was successfully achieved via Pd-catalyzed intramolecular C-N bond formation between the nitrogen originated from the aziridine and the halogen containing aromatic carbon. This reaction has a broad substrate scope to provide various enantiomerically pure (3,4-dihydro-2H-benzo[b][1,4]oxazin-3-yl)methanols, 2-hydroxymethyl-1,2,3,4-tetrahydroquinolines and (1,2,3,4-tetrahydroquinoxalin-2-yl)methanols from common chiral aziridines in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.027