1-[(R)-(4-chlorophenyl)[[(1'R)-1'-phenylethyl]amino]methyl]-2-naphthol | 354147-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[(R)-(4-chlorophenyl)[[(1'R)-1'-phenylethyl]amino]methyl]-2-naphthol
• 英文别名: 1-((R)-(4-chlorophenyl)-((R)-1-phenylethylamino)methyl)naphthalen-2-ol；1-[(R)-(4-chlorophenyl)-[[(1R)-1-phenylethyl]amino]methyl]naphthalen-2-ol
• CAS: 354147-36-7
• 化学式: C₂₅H₂₂ClNO
• 分子量: 387.909
• InChiKey: TVUNSHLFICJUJU-CRICUBBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.12
• 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：

  氯甲酸苄酯 、 1-[(R)-(4-chlorophenyl)[[(1'R)-1'-phenylethyl]amino]methyl]-2-naphthol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以99.5%的产率得到benzyl [(R)-(4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl][(R)-1-phenylethyl]carbamate
  参考文献：
  名称：

  使用新型手性亚磷酰胺对苯乙烯进行不对称氢化硅烷化

  摘要：

  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。

  DOI：

  10.1055/s-2008-1032199
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 4-氯苯甲醛 、 2-萘酚 在 三甲基氯硅烷 、 lithium perchlorate 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以78%的产率得到1-[(R)-(4-chlorophenyl)[[(1'R)-1'-phenylethyl]amino]methyl]-2-naphthol
  参考文献：
  名称：

  高氯酸锂在乙醚中介导的手性胺对萘酚的高度非对映选择性氨基烷基化

  摘要：

  在室温下，萘酚与原位制备的亚胺在5 M高氯酸锂中的一锅三组分曼尼希反应，可以高收率和高非对映选择性提供相应的氨基烷基化产物。该方法以2-萘酚与（R）-1-苯基乙胺和芳族醛在浓高氯酸锂醚溶液中的反应为例，这提供了对必要的2-氨基烷基化产物的高度非对映选择性。

  DOI：

  10.1016/s0957-4166(02)00863-7

文献信息

• Highly diastereoselective aminoalkylation of naphthols with chiral amines mediated by lithium perchlorate solution in diethyl ether
  作者：Mohammad R Saidi、Najmoddin Azizi

  DOI：10.1016/s0957-4166(02)00863-7

  日期：2003.2

  temperature affords the corresponding aminoalkylated products in high yields with high diastereoselectivities. The process is exemplified by the reaction of 2-naphthol with (R)-1-phenylethylamine and an aromatic aldehyde in concentrated ethereal lithium perchlorate solution, which affords a highly diastereoselective access to the requisite 2-aminoalkylated product.

  在室温下，萘酚与原位制备的亚胺在5 M高氯酸锂中的一锅三组分曼尼希反应，可以高收率和高非对映选择性提供相应的氨基烷基化产物。该方法以2-萘酚与（R）-1-苯基乙胺和芳族醛在浓高氯酸锂醚溶液中的反应为例，这提供了对必要的2-氨基烷基化产物的高度非对映选择性。
• 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.
• 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。