bis<(R)-1-<(tert-butyldimethylsilyl)oxy>-1-phenylethan-2-yl>amine | 150125-75-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: bis<(R)-1-<(tert-butyldimethylsilyl)oxy>-1-phenylethan-2-yl>amine
• 英文别名: bis[(R)-1-[(tert-butyldimethylsilyl)oxy]-1-phenylethan-2-yl]amine；(2R)-2-[tert-butyl(dimethyl)silyl]oxy-N-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-phenylethyl]-2-phenylethanamine
• CAS: 150125-75-0
• 化学式: C₂₈H₄₇NO₂Si₂
• 分子量: 485.858
• InChiKey: LHDTXBZZCRMUPP-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis<(R)-1-<(tert-butyldimethylsilyl)oxy>-1-phenylethan-2-yl>amine 在 吡啶 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 69.0h， 生成 (3R,17R)-3,17-diphenyl-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane
  参考文献：
  名称：

  Synthesis of chiral diaza-18-crown-6 derivatives from optically active diethanolamines

  摘要：

  Homotopic 1,10-diaza-18-crown-6 derivatives with two, four, and six chiral centers have been prepared in optically active form from diethanolamines via a cyclization reaction with tosylates 39 and 48. The requisite optically active diethanolamines were prepared from chiral cyanohydrins and chiral ethanolamines by a one-pot Grignard-transimination-reduction or a one-pot reduction-transimination-reduction procedure. Yields were strongly affected by the size of the substituents alpha to the nitrogen atom. The stereoselectivity of the diethanolamine synthesis was found to depend on the configuration of the ethanolamine used.

  DOI：

  10.1021/jo00068a029
• 作为产物：
  描述：

  (R)-(+)-α-<(tert-butyldimethylsilyl)oxy>-benzeneacetonitrile 在 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 反应 21.0h， 生成 bis<(R)-1-<(tert-butyldimethylsilyl)oxy>-1-phenylethan-2-yl>amine
  参考文献：
  名称：

  Synthesis of chiral diaza-18-crown-6 derivatives from optically active diethanolamines

  摘要：

  Homotopic 1,10-diaza-18-crown-6 derivatives with two, four, and six chiral centers have been prepared in optically active form from diethanolamines via a cyclization reaction with tosylates 39 and 48. The requisite optically active diethanolamines were prepared from chiral cyanohydrins and chiral ethanolamines by a one-pot Grignard-transimination-reduction or a one-pot reduction-transimination-reduction procedure. Yields were strongly affected by the size of the substituents alpha to the nitrogen atom. The stereoselectivity of the diethanolamine synthesis was found to depend on the configuration of the ethanolamine used.

  DOI：

  10.1021/jo00068a029

文献信息

• Stereoselective reduction of prochiral ketones, using aluminum hydride reagents prepared from lialh4 and chiral diethanolamines.
  作者：Erik F.J. de Vries、Johannes Brussee、Chris G. Knise、Arne van der Gen

  DOI：10.1016/s0957-4166(00)86209-6

  日期：1994.3

  The asymmetric reduction of prochiral ketones to chiral secondary alcohols by LiAIH4, modified with optically active diethanolamines, was studied. Asymmetric inductions of up to 94% were obtained with these reagents. The stereoselectivity of the reaction was found to depend both upon the temperature at which the reduction was performed and upon the conditions under which the chiral aluminum hydride

  研究了用光学活性二乙醇胺改性的LiAIH 4将手性酮不对称还原为手性仲醇。使用这些试剂可获得高达94％的不对称诱导。发现反应的立体选择性既取决于进行还原的温度，又取决于制备手性氢化铝试剂的条件。通过将手性助剂中的碳原子α处的取代基改变为氮，可以过量地获得仲醇的（R）-或（S）-对映体。
• Synthesis of chiral diaza-18-crown-6 derivatives from optically active diethanolamines
  作者：Erik F. J. de Vries、Pablo Steenwinkel、Johannes Brussee、Chris G. Kruse、Arne van der Gen

  DOI：10.1021/jo00068a029

  日期：1993.7

  Homotopic 1,10-diaza-18-crown-6 derivatives with two, four, and six chiral centers have been prepared in optically active form from diethanolamines via a cyclization reaction with tosylates 39 and 48. The requisite optically active diethanolamines were prepared from chiral cyanohydrins and chiral ethanolamines by a one-pot Grignard-transimination-reduction or a one-pot reduction-transimination-reduction procedure. Yields were strongly affected by the size of the substituents alpha to the nitrogen atom. The stereoselectivity of the diethanolamine synthesis was found to depend on the configuration of the ethanolamine used.