1-{(R)-[N-methyl-((1'R)-1'-phenylethyl)amino](phenyl)methyl}naphthalen-2-ol | 479578-05-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-{(R)-[N-methyl-((1'R)-1'-phenylethyl)amino](phenyl)methyl}naphthalen-2-ol
• 英文别名: 1-[(1R)-phenyl{methyl[(1'R)-1'-phenylethyl]amino}methyl]-2-naphthol；1-[(R)-[methyl-[(1R)-1-phenylethyl]amino]-phenylmethyl]naphthalen-2-ol
• CAS: 479578-05-7
• 化学式: C₂₆H₂₅NO
• 分子量: 367.491
• InChiKey: IQYSDEIINVPLRD-NIYFSFCBSA-N

物化性质

• 沸点：
  499.2±35.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 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：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-{(R)-[N-methyl-((1'R)-1'-phenylethyl)amino](phenyl)methyl}naphthalen-2-ol 在 palladium diacetate 、 三氯硅烷 、 1,3-双(二苯基膦)丙烷 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 34.0h， 生成 {(R)-[2-(diphenylphosphanyl)naphthalen-1-yl](phenyl)methyl}methyl((1R')-1'-phenylethyl)amine
  参考文献：
  名称：

  新型不对称催化手性氨基膦配体的合成

  摘要：

  本文介绍了一种由氨基萘酚原料合成的新型手性氨基膦配体，该原料是2-萘酚与（R）-1-苯基乙胺和苯甲醛的不对称1-氨基烷基化反应而得。还研究了丙二酸二甲酯在Pd（0）催化的1,3-二苯基丙-2-烯-1-基乙酸酯的Pd（0）催化的烯丙基取代中的配体的不对称诱导性质，其接近定量的收率和ee最高为在优化的反应条件下获得了72.2％的产物。

  DOI：

  10.1016/s0957-4166(02)00324-5
• 作为产物：
  描述：

  1-((R)-phenyl{[(R)-1-phenylethyl]amino}methyl)naphthalen-2-ol 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 9.0h， 生成 1-{(R)-[N-methyl-((1'R)-1'-phenylethyl)amino](phenyl)methyl}naphthalen-2-ol
  参考文献：
  名称：

  新型不对称催化手性氨基膦配体的合成

  摘要：

  本文介绍了一种由氨基萘酚原料合成的新型手性氨基膦配体，该原料是2-萘酚与（R）-1-苯基乙胺和苯甲醛的不对称1-氨基烷基化反应而得。还研究了丙二酸二甲酯在Pd（0）催化的1,3-二苯基丙-2-烯-1-基乙酸酯的Pd（0）催化的烯丙基取代中的配体的不对称诱导性质，其接近定量的收率和ee最高为在优化的反应条件下获得了72.2％的产物。

  DOI：

  10.1016/s0957-4166(02)00324-5

文献信息

• Synthesis of chiral calix[4]arenes bearing aminonaphthol moieties and their use in the enantiomeric recognition of carboxylic acids
  作者：Mustafa Durmaz、Mustafa Yilmaz、Abdulkadir Sirit

  DOI：10.1039/c0ob00399a

  日期：——

  exhibited different chiral recognition abilities towards the enantiomers of racemic materials and formed 2 : 1 or 1 : 1 complexes between host and guest. It was also demonstrated that chiral calix[4]arenes 9 and 16 could be used as chiral NMR solvating agents to determine the enantiomeric purity of mandelic acid.

  制备了两个在下部边缘用手性氨基萘酚官能化的武装手性杯[4]芳烃8-16，并通过FTIR，1 H和13 C，DEPT和COZY NMR光谱学和元素分析对这些受体的结构进行了表征。通过1 H NMR和UV / Vis光谱研究了这些受体与各种羧酸的对映选择性识别。受体对外消旋物质的对映异构体表现出不同的手性识别能力，并在宿主和客体之间形成2：1或1：1的复合物。还证明手性杯[4]芳烃9和16 可以用作手性NMR溶剂来确定对映体的纯度 扁桃酸。
• Chiral calix[4]arenes bearing aminonaphthol moieties as membrane carriers for amino acid methyl esters and mandelic acid
  作者：Mustafa Durmaz、Selahattin Bozkurt、Hayriye Nevin Naziroglu、Mustafa Yilmaz、Abdulkadir Sirit

  DOI：10.1016/j.tetasy.2011.04.019

  日期：2011.4

  Chiral calix[4]arene derivatives functionalized at the lower rim with chiral aminonaphthol units have been prepared. The structures of these receptors were characterized by a combination of (1)H NMR, (13)C NMR, FTIR and elemental analysis. The transport of amino acid derivatives (phenylglycine, phenylalanine and tryptophan methyl ester hydrochlorides) and mandelic acid were studied through a bulk liquid membrane in the presence of chiral calix[4]arene derivatives. The transport rate and enantioselectivity of the amino acid esters studied depended mainly upon the structure of the chiral receptors. The influence of calixarene and amino acid ester structures upon transport through a liquid membrane is discussed. The receptors with hydrogen bonding sites and aromatic groups showed considerable higher transport rates and stereoselectivities. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of a new type of chiral amino phosphine ligands for asymmetric catalysis
  作者：Yi Wang、Xin Li、Kuiling Ding

  DOI：10.1016/s0957-4166(02)00324-5

  日期：2002.7

  This article describes the synthesis of a new type of chiral amino phosphine ligands from an amino naphthol starting material derived by asymmetric 1-aminoalkylation of 2-naphthol with (R)-1-phenylethylamine and benzaldehyde. The asymmetric induction properties of the ligands in the Pd(0)-catalyzed allylic substitution of 1,3-diphenylprop-2-en-1-yl acetate with dimethyl malonate has also been investigated

  本文介绍了一种由氨基萘酚原料合成的新型手性氨基膦配体，该原料是2-萘酚与（R）-1-苯基乙胺和苯甲醛的不对称1-氨基烷基化反应而得。还研究了丙二酸二甲酯在Pd（0）催化的1,3-二苯基丙-2-烯-1-基乙酸酯的Pd（0）催化的烯丙基取代中的配体的不对称诱导性质，其接近定量的收率和ee最高为在优化的反应条件下获得了72.2％的产物。
• 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.