(R)-1-<<(tert-butyldimethylsilyl)oxy>-1-phenylethan-2-yl>-amine | 150125-74-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-<<(tert-butyldimethylsilyl)oxy>-1-phenylethan-2-yl>-amine
• 英文别名: (R)-2-(tert-butyldimethylsilyloxy)-2-phenylethanamine；(2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-phenylethanamine
• CAS: 150125-74-9
• 化学式: C₁₄H₂₅NOSi
• 分子量: 251.444
• InChiKey: ODNBGJYRQGSECA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (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：

  叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 6.83h， 生成 (R)-1-<<(tert-butyldimethylsilyl)oxy>-1-phenylethan-2-yl>-amine
  参考文献：
  名称：

  温和高效的对映选择性合成堇酰亚胺B全立体异构体及其抗氧化研究

  摘要：

  通过(S)-2-氨基-1-苯基乙醇和(R)-2-氨基-1-苯基乙醇与L-谷氨酸和D-谷氨酸的耦合反应，合成了cordiarimide B的四种异构体。生物学研究表明，其中两种异构体表现出强大的抗氧化活性。在这两种异构体中，最有前景的是化合物(3S,11S) 18，其活性是(3S,11R) 20异构体的四倍。另外两种异构体（3R,11S）22和（3R,11R）24在生物学上不活跃。结构-活性关系研究表明，在2-氨基-1-苯基乙醇的C-3位上的羟基(-OH)的立体化学在调节抗氧化活性方面起着关键作用。这一发现可以帮助合理设计cordiarimide B作为新型抗氧化药物分子。

  DOI：

  10.14233/ajchem.2018.21170

文献信息

• A simple chiral derivatisation protocol for 1H NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols
  作者：Magdalena E. Powell、Andrew M. Kelly、Steven D. Bull、Tony D. James

  DOI：10.1016/j.tetlet.2008.12.013

  日期：2009.2

  A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by 1H NMR spectroscopic analysis is described, which involves their treatment with 2-formylphenylboronic acid and enantiopure (syn)-methyl-2,3-dihydroxy-3-phenylpropionate to afford mixtures of imino-boronate esters whose diastereoisomeric ratio is an accurate reflection of the enantiopurity

  描述了一种简单的手性衍生方案，可通过1 H NMR光谱分析确定O-甲硅烷基保护的1,2-氨基醇的对映体纯度，涉及用2-甲酰基苯基硼酸和对映纯（syn）-甲基-2处理3-二羟基-3-苯基丙酸酯提供亚氨基-硼酸酯的混合物，其非对映异构体比率准确反映了母体氨基醇的对映体纯度。
• 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.
• Mild and Efficient Enantioselective Synthesis of All Stereoisomers of Cordiarimide B and Their Antioxidant Study
  作者：B.V. Jeevan、M. Umashankara、Y.C. Sunil Kumar、M.N. Kumara、K.S. Rangappa

  DOI：10.14233/ajchem.2018.21170

  日期：——

  Four isomers of cordiarimide B were synthesized by coupling (S)-2-amino-1-phenylethanol and (R)-2-amino-1-phenylethanol with L and D glutamic acid. Biological studies revealed that two isomers showed potent antioxidant activity. Among these two, the most promising isomer is compound (3S,11S) 18, possesses four folds more active than the (3S,11R) 20 isomer. The other two isomers (3R,11S) 22 and (3R,11R) 24 are biologically not active. Structure-activity relationship studies indicated that the stereochemistry of the hydroxyl (-OH) group at C-3 position of 2-amino-1-pheylehtnaol played a crucial role in modulating the antioxidant activity. This finding could help in rational designing of cordiarimide B as novel antioxidant drug molecules.

  通过(S)-2-氨基-1-苯基乙醇和(R)-2-氨基-1-苯基乙醇与L-谷氨酸和D-谷氨酸的耦合反应，合成了cordiarimide B的四种异构体。生物学研究表明，其中两种异构体表现出强大的抗氧化活性。在这两种异构体中，最有前景的是化合物(3S,11S) 18，其活性是(3S,11R) 20异构体的四倍。另外两种异构体（3R,11S）22和（3R,11R）24在生物学上不活跃。结构-活性关系研究表明，在2-氨基-1-苯基乙醇的C-3位上的羟基(-OH)的立体化学在调节抗氧化活性方面起着关键作用。这一发现可以帮助合理设计cordiarimide B作为新型抗氧化药物分子。