(S)-2-amino-1,2,2-triphenylethanol | 220088-97-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S)-2-amino-1,2,2-triphenylethanol
• 英文别名: (1S)-2-amino-1,2,2-triphenylethanol
• CAS: 220088-97-1
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: HACVWKBZOPTVSY-IBGZPJMESA-N

物化性质

• 熔点：
  166 °C
• 沸点：
  452.459±40.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.163±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-叔丁基-2-羟基-5-硝基苯甲醛 、 (S)-2-amino-1,2,2-triphenylethanol 在 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 以73%的产率得到(S)-2-(1,1-dimethylethyl)-6-{[(E)-(2-hydroxy-1,1,2-triphenylethyl)imino]methyl}-4-nitrophenol
  参考文献：
  名称：

  区域异构的三苯基氨基乙醇–对映选择性催化效率的比较

  摘要：

  新型氨基醇（R）-和（S）-2的两种对映体均由扁桃酸衍生的乙二醇3的相应对映体制备。区域异构的氨基醇1和2分别转化为亚胺7和8。由其衍生的钛络合物9和10用作催化剂，用于将二乙基锌加成到苯甲醛中，并产生高达92％ee的醇11。另一方面，氯取代的钛络合物14和15能够介导二酮16的Torgov环化反应，得到雌酮衍生物17。在两个反应中，新的氨基醇2衍生的钛配合物10和15都比基于区域异构氨基醇1的配合物9和14具有更高的对映选择性。

  DOI：

  10.1002/adsc.200303178
• 作为产物：
  描述：

  (S)-2,2,3-triphenyloxirane 在 palladium on activated charcoal Ti(N3)2(OiPr)2 、 硫酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 11.5h， 生成 (S)-2-amino-1,2,2-triphenylethanol
  参考文献：
  名称：

  Highly Efficient Synthesis of Enantiomerically Pure (S)-2-Amino-1,2,2-triphenylethanol. Development of a New Family of Ligands for the Highly Enantioselective Catalytic Ethylation of Aldehydes

  摘要：

  The reaction of (S)-triphenylethylene oxide (3) with diisopropoxytitanium(IV) diazide in benzene solution at 70 degrees C takes place readily in a completely regioselective and stereospecific manner to afford (S)-2-azido-1,2,2-triphenylethanol (6). Reduction of the azide by catalytic hydrogenation leads to (S)-2-amino-1,2,2-triphenylethanol (5) that, by N,N-dialkylation with 1,4-dibromobutane, 1,5-dibromopentane, 1,5-dibromo-3-oxapentane, alpha,alpha'- dibromo-o-xylene, and methyl iodide, affords the corresponding (S)-2-dialkylamina-1,2,2-triphenylethanols (7a-e). On the other hand, the reaction of 5 with benzyl bromide or 1-iodobutane takes place as a monoalkylation, leading to the corresponding (S)-2-alkylamino-1,2,2-triphenylethanols (8f,g). The performance of amino alcohols 7a-e as ligands for the catalytic enantioselective addition of diethylzinc to benzaldehyde has been studied, with enantioselectivities of 94-97% being recorded. The best performing ligands in this family; 7a [(S)-1,2,2-triphenyl-2-(1-pynolidinyl)-ethanol] and 7c [(S)-2-morpholino-1,2,2-triphenylethanol] have been studied in the addition of Et2Zn to a representative family of aldehydes. With 7a, a 96.6% mean ee is recorded for a family of 16 alpha-substituted aldehydes and a 92.8% mean ee for a family of six alpha-unsubstituted aldehydes. With 7c working on the same families of aldehydes, the mean enantioselectivities are 96.8% and 91.8%, respectively.

  DOI：

  10.1021/jo982442n

文献信息

• Bis-Chelated Imine-Alkoxytitanium Complexes: Novel Chiral Dopants with High Helical Twisting Power in Liquid Crystals
  作者：Manfred Braun、Antje Hahn、Marco Engelmann、Ralf Fleischer、Walter Frank、Carola Kryschi、Sylke Haremza、Katrin Kürschner、Robert Parker

  DOI：10.1002/chem.200401292

  日期：2005.5.20

  imine-alkoxytitanium complexes 6 and 7 have been synthesized and used as chiral dopants for converting nematic into cholesteric phases. The dopants were tested in mainly commercially available nematic liquid crystalline compounds or mixtures: LC1 (BASF), ZLI-1695 and ZLI-1840 (Merck), as well as N-(4-methoxybenzylidene)-4'-butylaniline (MBBA). The values of the helical twisting power (HTP) were determined by the

  对映体和非对映体纯的双螯合的亚胺-烷氧基钛配合物6和7已经合成，并用作手性掺杂剂，用于将向列相转化为胆甾相。在主要可商购的向列型液晶化合物或混合物中测试掺杂剂：LC1，BASF，ZLI-1695和ZLI-1840（默克），以及N-（4-甲氧基亚苄基）-4'-丁基苯胺（MBBA）。螺旋扭转力（HTP）的值通过Grandjean-Cano方法确定。获得了极高的螺旋扭曲力。因此，钛配合物6 h在MBBA中显示740 microm（-1）的HTP值，据报道是最高的HTP值。已经发现螺旋扭转能力强烈地依赖于向列相的结构和钛络合物6和7中手性配体的取代方式。6 f的晶体结构分析证实了该金属络合物的A，R，R构型。手性亚胺配体4和5衍生自区域异构的氨基醇1和2。
• 2-Amino-1,2,2-triphenylethanol: A Novel Chiral Reagent Containing the Diphenylaminomethyl Group. Enantioselective Addition of Diethylzinc to Benzaldehyde
  作者：Ralf Fleischer、Manfred Braun

  DOI：10.1055/s-1998-1953

  日期：1998.12

  The novel chiral amino alcohols (R)- and (S)-1 are prepared from the corresponding enantiomer of ethanediol 2. Alkoxytitanium complexes of the imines 8 derived from 1 are suitable to catalyze the addition of diethylzinc to benzaldehyde in up to 92% e.e.

  新型手性氨基醇 (R)- 和 (S)-1 是由乙二醇 2 的相应对映体制备的。由 1 衍生出的亚胺 8 的烷氧基钛络合物适用于催化二乙基锌与苯甲醛的加成反应，其催化效率高达 92%。
• Highly Efficient Synthesis of Enantiomerically Pure (<i>S</i>)-2-Amino-1,2,2-triphenylethanol. Development of a New Family of Ligands for the Highly Enantioselective Catalytic Ethylation of Aldehydes
  作者：Katamreddy Subba Reddy、Lluís Solà、Albert Moyano、Miquel A. Pericàs、Antoni Riera

  DOI：10.1021/jo982442n

  日期：1999.5.1

  The reaction of (S)-triphenylethylene oxide (3) with diisopropoxytitanium(IV) diazide in benzene solution at 70 degrees C takes place readily in a completely regioselective and stereospecific manner to afford (S)-2-azido-1,2,2-triphenylethanol (6). Reduction of the azide by catalytic hydrogenation leads to (S)-2-amino-1,2,2-triphenylethanol (5) that, by N,N-dialkylation with 1,4-dibromobutane, 1,5-dibromopentane, 1,5-dibromo-3-oxapentane, alpha,alpha'- dibromo-o-xylene, and methyl iodide, affords the corresponding (S)-2-dialkylamina-1,2,2-triphenylethanols (7a-e). On the other hand, the reaction of 5 with benzyl bromide or 1-iodobutane takes place as a monoalkylation, leading to the corresponding (S)-2-alkylamino-1,2,2-triphenylethanols (8f,g). The performance of amino alcohols 7a-e as ligands for the catalytic enantioselective addition of diethylzinc to benzaldehyde has been studied, with enantioselectivities of 94-97% being recorded. The best performing ligands in this family; 7a [(S)-1,2,2-triphenyl-2-(1-pynolidinyl)-ethanol] and 7c [(S)-2-morpholino-1,2,2-triphenylethanol] have been studied in the addition of Et2Zn to a representative family of aldehydes. With 7a, a 96.6% mean ee is recorded for a family of 16 alpha-substituted aldehydes and a 92.8% mean ee for a family of six alpha-unsubstituted aldehydes. With 7c working on the same families of aldehydes, the mean enantioselectivities are 96.8% and 91.8%, respectively.
• The Regioisomeric Triphenylaminoethanols–Comparison of their Efficiency in Enantioselective Catalysis
  作者：Manfred Braun、Ralf Fleischer、Brigitte Mai、Marc-André Schneider、Stefan Lachenicht

  DOI：10.1002/adsc.200303178

  日期：2004.3

  Both enantiomers of the novel amino alcohol (R)- and (S)-2 are prepared from the corresponding enantiomer of the mandelic acid-derived ethanediol 3. The regioisomeric amino alcohols 1 and 2 are converted into the imines 7 and 8, respectively. Titanium complexes 9 and 10 derived therefrom are used as catalysts for the addition of diethylzinc to benzaldehyde and yield the alcohol 11 in up to 92% ee.

  新型氨基醇（R）-和（S）-2的两种对映体均由扁桃酸衍生的乙二醇3的相应对映体制备。区域异构的氨基醇1和2分别转化为亚胺7和8。由其衍生的钛络合物9和10用作催化剂，用于将二乙基锌加成到苯甲醛中，并产生高达92％ee的醇11。另一方面，氯取代的钛络合物14和15能够介导二酮16的Torgov环化反应，得到雌酮衍生物17。在两个反应中，新的氨基醇2衍生的钛配合物10和15都比基于区域异构氨基醇1的配合物9和14具有更高的对映选择性。