N-<(S)-2-Hydroxypropyl>-N-<(S)-α-methylbenzyl>amine | 90687-83-5

• 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-<(S)-α-methylbenzyl>amine
• 英文别名: (S)-1-[N-(S)-α-phenylethyl]amino-2-propanole；(S)-1-((S)-α-phenylethylamino)-2-propanol；(2S)-1-[[(1S)-1-phenylethyl]amino]propan-2-ol
• CAS: 90687-83-5
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: NFXLZPVBFZLNKO-UWVGGRQHSA-N

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-<(S)-α-methylbenzyl>amine 在 lithium tetrachloropalladate 、 copper dichloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 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)-(-)- α-甲基苄胺 在 lithium aluminium tetrahydride 作用下， 生成 N-<(S)-2-Hydroxypropyl>-N-<(S)-α-methylbenzyl>amine
  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

文献信息

• Catalytic Asymmetric Transfer Hydrogenation of Ketones Using [Ru(p-cymene)Cl2]2 with Chiral Amino Alcohol Ligands
  作者：Sudhindra H. Deshpande、Ashutosh A. Kelkar、Rajesh G. Gonnade、Savita K. Shingote、Raghunath V. Chaudhari

  DOI：10.1007/s10562-010-0408-y

  日期：2010.9

  Catalytic asymmetric transfer hydrogenation of aromatic alkyl ketones has been investigated using [Ru(p-cymene)Cl2]2 and new derivatives of β-amino alcohols synthesized from (S)-(−)-lactic acid and mandelic acid as ligands. Chiral secondary alcohols were obtained with good to excellent conversion (60–90%) and moderate to good enantioselectivities (40–86%).Graphical AbstractAsymmetric transfer hydrogenation

  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。
• Synthesis of<i>C</i>₂-Symmetric Chiral Amino Alcohols: Their Usage as Organocatalysts for Enantioselective Opening of Epoxide Ring
  作者：Yilmaz Turgut、Tarik Aral、Mehmet Karakaplan、Pinar Deniz、Halil Hosgoren

  DOI：10.1080/00397910903419878

  日期：2010.10.20

  A series of β-amino alcohols derivatives were synthesized from (R)-2-amino-1-butanol and (S)-1,2-propanediol, and they have been used as organocatalaysts in the racemic ring opening of epoxide in good yields with high enantiomeric excess (up to 97%).

  以(R)-2-氨基-1-丁醇和(S)-1,2-丙二醇为原料合成了一系列β-氨基醇衍生物，并以良好的收率在环氧化物的外消旋开环中用作有机催化剂对映体过量（高达 97%）。
• 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。
• Synthesis of novel C2-symmetric chiral crown ethers and investigation of their enantiomeric recognition properties
  作者：Yilmaz Turgut、Tarik Aral、Halil Hosgoren

  DOI：10.1016/j.tetasy.2009.09.010

  日期：2009.10

  A series of new C2-symmetric chiral aza crown ether macrocycles 1–4 have been synthesized from (S)-3-aryloxy-1,2-propanediol and (S)-1,2-propanediol for the enantiomeric recognition of amino acid ester derivatives. These new macrocycles have been shown to be strong complexing agents for primary organic ammonium salts (with K up to 176.93 M−1 and ΔG° up to 12.81 kJ mol−1) by 1H NMR titration. These

  一系列新的c ^ 2 -对称的手性氮杂冠醚大环化合物1 - 4已经从（合成小号）-3-芳氧基-1,2-丙二醇和（小号）-1,2-丙二醇为对映异构体识别氨基酸的酯衍生物。通过1 H NMR滴定显示，这些新的大环化合物是伯有机铵盐（K最高为176.93 M -1和ΔG °最高为12.81 kJ mol -1）的强络合剂。这些大环主体对苯丙氨酸甲酯盐酸盐的D-对映异构体具有K D /的对映选择性键。在具有0.25％CD 3 OD的CDCl 3中，K L高达6.87 。
• Pyridine-containing chiral macrocycles for the enantioselective recognition of amino acid derivatives and their molecular dynamics simulations
  作者：Yilmaz Turgut、Safak Ozhan Kocakaya

  DOI：10.1016/j.tetasy.2010.05.038

  日期：2010.4

  enantiomeric recognition of amino acid ester derivatives. These novel macrocycles have been shown to be strong complexing agents for primary organic ammonium salts (with K values of up to 1363.5 M−1, ΔGo of up to 17.86 kJ mol−1 and a selectivity ratio of 80:20) by 1H NMR titration method. These macrocyclic host exhibited enantioselective binding towards the l-enantiomer of phenylalanine methyl ester hydrochloride

  由（S）-1,2-丙二醇和（S）-3-芳氧基制备了两个新的C 2对称光学活性吡啶-15-冠-5型配体，它们在立体中心具有亲脂性链，大环5和6。-1,2-丙二醇用于氨基酸酯衍生物的对映体识别。这些新的大环化合物已被证明是用于初级有机铵盐强络合剂（具有ķ最多的值，以1363.5中号-1，Δ ģ Ò向上的至17.86千焦摩尔-1和80:20的选择性比率）由11 H NMR滴定法。这些大环主体在含有0.25％CD 3 OD的CDCl 3中显示出对苯丙氨酸甲酯盐酸盐的I-对映异构体的对映选择性结合，其中K L / K D高达8.57 。实验结果已在原子级进行了分子动力学计算，涉及手性pyridino-15-crown-5的分子识别和区分特性。结合自由能经计算为〜-25kJ mol -1。结果表明宿主比苯丙氨酸盐更好地结合和区分缬氨酸盐。分子动力学，MM / PBSA计算与1 H NMR结果一致。