1-[(R)-(4-methylphenyl)[[(1'R)-1'-phenylethyl]amino]methyl]-2-naphthol | 354147-34-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(R)-(4-methylphenyl)[[(1'R)-1'-phenylethyl]amino]methyl]-2-naphthol
• 英文别名: 1-[(R)-(4-methylphenyl)-[[(1R)-1-phenylethyl]amino]methyl]naphthalen-2-ol
• CAS: 354147-34-5
• 化学式: C₂₆H₂₅NO
• 分子量: 367.491
• InChiKey: ASRVFCLCERMAHO-NIYFSFCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  1-[(R)-(4-methylphenyl)[[(1'R)-1'-phenylethyl]amino]methyl]-2-naphthol 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 生成 1-[(R)-(4-methylphenyl){methyl[(1'R)-1'-phenylethyl]amino}methyl]-2-naphthol
  参考文献：
  名称：

  A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde

  摘要：

  A practical procedure for the stereoselective synthesis of a wide group of functionalized aminoalkylnaphthols, using inexpensive starting materials, is reported. Selective N-alkylation was carried out by cyclization of secondary aminoalkylnaphthols with formaldehyde, followed by reduction or alkylation with organometallic reagents. The catalytic activity of this class of compounds was tested in the addition of diethylzine to benzaldehyde, resulting in moderate to good enantio selectivities. It is noteworthy that the aminonaphthols obtained as the major diastereomer in the solvent free synthesis, have the best asymmetric induction properties in the alkylation reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00651-1
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 对甲基苯甲醛 、 2-萘酚 反应 8.0h， 以72%的产率得到1-[(R)-(4-methylphenyl)[[(1'R)-1'-phenylethyl]amino]methyl]-2-naphthol
  参考文献：
  名称：

  Solvent-Free Asymmetric Aminoalkylation of Electron-Rich Aromatic Compounds:  Stereoselective Synthesis of Aminoalkylnaphthols by Crystallization-Induced Asymmetric Transformation

  摘要：

  Electron-rich aromatic compounds such as 2-naphthol give a faster and asymmetric 1-aminoalkylation with high yields when treated with (R)-1-phenylethylamine and aromatic aldehydes in solvent-free conditions. An asymmetric transformation of a second kind, probably induced by the preferential crystallization of one diastereomer, affords the straightforward and stereoselective synthesis of aminoalkylnaphthols. Mechanisms predictable for this asymmetric reaction are reported. The absolute configurations and the conformations of the unknown aminonaphthols are widely ascertained.

  DOI：

  10.1021/jo0101205

文献信息

• Asymmetric Hydrosilylation of Styrenes by Use of New Chiral ­Phosphoramidites
  作者：Xinsheng Li、Jianan Song、Dongcheng Xu、Lichun Kong

  DOI：10.1055/s-2008-1032199

  日期：2008.3

  New chiral phosphoramidites were synthesized from chiral unsymmetrical amines and BINOL in good yields. Enantioselective hydrosilylation of styrenes with trichlorosilane in the presence of palladium complexes of these ligands provided chiral silanes in medium to high yields. Oxidation of these chiral silanes with hydrogen peroxide gave the corresponding chiral secondary alcohols in up to 97% ee.

  由手性不对称胺和 BINOL 合成了新的手性亚磷酰胺，收率良好。在这些配体的钯配合物存在下，苯乙烯与三氯硅烷的对映选择性氢化硅烷化以中等至高产率提供手性硅烷。用过氧化氢氧化这些手性硅烷得到相应的手性仲醇，最高可达 97% ee。
• Solvent-Free Asymmetric Aminoalkylation of Electron-Rich Aromatic Compounds:  Stereoselective Synthesis of Aminoalkylnaphthols by Crystallization-Induced Asymmetric Transformation
  作者：Cristina Cimarelli、Andrea Mazzanti、Gianni Palmieri、Emanuela Volpini

  DOI：10.1021/jo0101205

  日期：2001.7.1

  Electron-rich aromatic compounds such as 2-naphthol give a faster and asymmetric 1-aminoalkylation with high yields when treated with (R)-1-phenylethylamine and aromatic aldehydes in solvent-free conditions. An asymmetric transformation of a second kind, probably induced by the preferential crystallization of one diastereomer, affords the straightforward and stereoselective synthesis of aminoalkylnaphthols. Mechanisms predictable for this asymmetric reaction are reported. The absolute configurations and the conformations of the unknown aminonaphthols are widely ascertained.
• Development of chiral heteroleptic magnesium amides; asymmetric deprotonations mediated by six-membered metallocyclic amidomagnesium naphtholates
  作者：Emma L. Carswell、William J. Kerr、Duncan McArthur、Marek Pažický、Allan J.B. Watson

  DOI：10.1016/j.tet.2014.06.052

  日期：2014.10

  A series of enantioenriched six-membered metallocyclic amidomagnesium naphtholates were prepared and used to probe the structure-reactivity/selectivity relationships of heteroleptic magnesium base complexes within asymmetric deprotonation reactions. An effective complex was identified and applied within enantioselective enolisation processes, delivering good levels of enantioselectivity and also revealing key structural requirements for achieving such selectivity. (C) 2014 Elsevier Ltd. All rights reserved.
• A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde
  作者：Cristina Cimarelli、Gianni Palmieri、Emanuela Volpini

  DOI：10.1016/s0957-4166(02)00651-1

  日期：2002.11

  A practical procedure for the stereoselective synthesis of a wide group of functionalized aminoalkylnaphthols, using inexpensive starting materials, is reported. Selective N-alkylation was carried out by cyclization of secondary aminoalkylnaphthols with formaldehyde, followed by reduction or alkylation with organometallic reagents. The catalytic activity of this class of compounds was tested in the addition of diethylzine to benzaldehyde, resulting in moderate to good enantio selectivities. It is noteworthy that the aminonaphthols obtained as the major diastereomer in the solvent free synthesis, have the best asymmetric induction properties in the alkylation reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.