N-<(S)-2-Hydroxypropyl>-N-<(R)-α-methylbenzyl>amine | 90687-82-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-<(S)-2-Hydroxypropyl>-N-<(R)-α-methylbenzyl>amine
• 英文别名: (S)-1-[N-(R)-α-phenylethyl]amino-2-propanole；(S)-1-[N-(R)-α-phenylethyl]amino-2-propanol；(2S)-1-[[(1R)-1-phenylethyl]amino]propan-2-ol
• CAS: 90687-82-4
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: NFXLZPVBFZLNKO-VHSXEESVSA-N

物化性质

• 熔点：
  53-54 °C
• 沸点：
  294.8±15.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<(S)-2-Hydroxypropyl>-N-<(R)-α-methylbenzyl>amine 在 lithium tetrachloropalladate 、 copper dichloride 作用下， 反应 36.0h， 生成
  参考文献：
  名称：

  Stereochemistry and regiochemistry of heteroatom directed reactions. Part 4. Palladium(II)-catalyzed synthesis of optically active tetrahydro-1,4-oxazine derivatives

  摘要：

  Three different types of morpholine derivatives 1-3 could be obtained from allylic amine substrates 4 in high yield and excellent diastereoselectivity by slight, variation of the Pd(II)-Cu(II) reagents system.

  DOI：

  10.1021/jo00070a001
• 作为产物：
  描述：

  (S)-2-hydroxy-N-((R)-1-phenylethyl)propanamide 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 以2.5 g的产率得到N-<(S)-2-Hydroxypropyl>-N-<(R)-α-methylbenzyl>amine
  参考文献：
  名称：

  使用 [Ru(p-cymene)Cl2]2 与手性氨基醇配体催化不对称转移氢化酮

  摘要：

  已经使用 [Ru(p-cymene)Cl2]2 和由 (S)-(-)-乳酸和扁桃酸合成的 β-氨基醇的新衍生物作为配体研究了芳族烷基酮的催化不对称转移氢化。获得了具有良好至优异转化率 (60–90%) 和中等至良好对映选择性 (40–86%) 的手性仲醇。图文摘要使用 [Ru(p-cymene)Cl2]2 和 β 研究了酮的不对称转移氢化-氨基醇由(S)-(-)-乳酸和扁桃酸作为配体合成。获得了具有良好至优异转化率（60-90%）和中等至良好对映选择性（40-86%）的手性仲醇。

  DOI：

  10.1007/s10562-010-0408-y

文献信息

• Synthesis of β-Amino Alcohols via the Reduction of Lactamides Derived from Ethyl (2S)-Lactate with Borane-Methyl Sulfide
  作者：David Grayson、Frank Lewis、Matthias Eichler

  DOI：10.1055/s-0029-1217538

  日期：2009.7

  Reactions of ethyl (2S)-lactate with various amines affords lactamides that are reduced with borane-methyl sulfide in the presence of boron trifluoride etherate to generate enantiomerically pure β-amino alcohols in good yield.

  (2S)-乳酸乙酯与各种胺反应得到乳酰胺，在三氟化硼醚合物存在下，用甲硼烷-甲硫醚还原乳酰胺，以良好的收率生成对映异构纯的 β-氨基醇。
• Biological assays, electrochemical behavior, and theoretical DFT calculations of Ru(II) complexes of chiral phosphinite based based on β-amino alcohols: Transfer hyrogenation of ketones using a HCOOH/Et3N mixture
  作者：Khadichakhan Rafikova、Nermin Meriç、Nil Ertekin Binbay、Veysi Okumuş、M. Şerif Sever、Yelizaveta Belyankova、Saniya Tursynbek、Anuar Dauletbakov、Bayazit Sarah、Darya Zolotareva、Kamshyger Yerassyl、Abdurahman Dündar、Remziye Güzel、Murat Aydemir

  DOI：10.1016/j.molstruc.2024.137556

  日期：2024.5

  bacteria were studied. Finally, the ruthenium complex, (2S)-1-[(2S)-2-[(diphenylphosphanyl)oxy]propyl][(1R)-1-phenylethyl]amino}propan-2-yldiphenyl phosphinitobis[dichloro(η6-benzene)ruthenium(II)] also catalyzed asymmetric transfer hydrogenation of acetophenone with high conversion (up to 99%) and good enantioselectivity (ee up to 89 %), in the existence of formic acid and triethylamine in dichloromethane

  已经证明了基于β-氨基醇的两种次亚膦酸酯配体的高产率合成。当我们用螯合次亚膦配体处理[Ru(芳烃)(μ-Cl)Cl] 2 芳烃:对伞花烃,苯}时，我们得到了具有通式[Ru(芳烃)次亚膦酸酯Cl 2的中性Ru(II)-配合物]。使用分析和光谱技术确认了配体和复合物的结构。在气相DFT/CAM-B3LYP理论水平上对钌配合物进行了量子化学计算。对次亚膦酸盐配合物进行了循环伏安法研究，以确定 HOMO 和 LUMO 能级的能量并估计其电化学和一些电子特性。使用TiO 2修饰的ITO电极固定基于有机络合物的记忆基板，并通过计时电流法(CA)和开路电位安培法(OCPA)验证基于次亚膦酸酯的有机络合物的记忆功能。在本研究中，还测定了钌基对伞花烃和苯络合物通过 DPPH 自由基清除、金属螯合和还原力活性的抗氧化潜力。此外，还研究了这些复合物对病原菌的 DNA 结合能力和抗菌活性。最后，钌络合物，(2S
• New functional chiral P-based ligands and application in ruthenium-catalyzed enantioselective transfer hydrogenation of ketones
  作者：Nermin Meriç、Cezmi Kayan、Nevin Gürbüz、Mehmet Karakaplan、Nil Ertekin Binbay、Murat Aydemir

  DOI：10.1016/j.tetasy.2017.10.004

  日期：2017.12

  Metal-catalyzed asymmetric transfer hydrogenation is a powerful and practical method for the reduction of ketones to produce the corresponding secondary alcohols, which are valuable building blocks in the pharmaceutical, perfume, and agrochemical industries. Hence, a series of novel chiral beta-amino alcohols were synthesized by chiral amines with regioselective ring opening of (S)-propylene oxide or reaction with (S)-(+)-2-hydroxypropyl p-toluenesulfonate by a straightforward method. The chiral ruthenium catalytic systems generated from [Ru(arene)(mu-Cl)Cl](2) complexes and chiral phosphinite ligands based on amino alcohol derivatives were employed in asymmetric transfer hydrogenation of ketones to give the corresponding optically active alcohols; (2S)-1-([(2.9-2-[(diphenylphosphanypoxylpropyl][(1R)-1-phenylethyl]amino}propan-2-yldiphenylphosphinitobis[dichol-oro(eta(6)-benzene)ruthenium(II)] acts an excellent catalyst in the reduction of cl-naphthyl methyl ketone, giving the corresponding alcohol with up to 99% ee. The substituents on the backbone of the ligands were found to have a remarkable effect on both the conversion and enantioselectivity of the catalysts. Furthermore, this transfer hydrogenation is characterized by low reversibility under these conditions. (C) 2017 Elsevier Ltd. All rights reserved.
• Yoneyama, Koichi; Ichizen, Nobumasa; Konnai, Makoto, Agricultural and Biological Chemistry, 1984, vol. 48, # 4, p. 995 - 1000
  作者：Yoneyama, Koichi、Ichizen, Nobumasa、Konnai, Makoto、Takematsu, Tetsuo、Ushinohama, Kazuyuki、Jikihara, Tetsuo

  DOI：——

  日期：——