(R)-N-1-(4-methoxphenyl)ethyl-2-oxo-1-naphthaldimine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-N-1-(4-methoxphenyl)ethyl-2-oxo-1-naphthaldimine
• 英文别名: (R)-N-1-ethyl-2-oxo-1-naphthaldimine；(R)-N-1-(p-methoxyphenyl)ethyl-2-hydroxy-1-naphthaldimine；(R)-N-(4-methoxyphenyl)ethyl-2-hydroxy-1-naphthaldimine；(R)-N-[1-(4-methoxyphenyl)ethyl]-2-hydroxy-1-naphthaldimine；1-[[(1R)-1-(4-methoxyphenyl)ethyl]iminomethyl]naphthalen-2-ol
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: JJQFPNVAFKXGDH-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) 、 (R)-N-1-(4-methoxphenyl)ethyl-2-oxo-1-naphthaldimine 以 甲醇 、 苯 为溶剂， 以85%的产率得到(η4-cycloocta-1,5-diene)((R)-N-(4-methoxyphenyl)ethyl-2-oxo-1-naphthaldiminato-κ(2)N,O)rhodium(I)
  参考文献：
  名称：

  [Rh {N，O}（eta4-cod）]与{N，O} =水杨基亚胺基希夫碱或氨基羧基配体的配合物中的多晶型物，对映体，手性和螺旋度。

  摘要：

  二聚配合物乙酰（eta4-环辛-1,5-二烯）铑（I），[Rh（O2CMe）（eta4-cod）] 2（cod =环辛-1,5-二烯）与N，O螯合反应席夫碱配体或与N-苯基甘氨酸配制成二氨基或氨基羧基的（4-环辛-1,5-二烯）铑（I）络合物[{Rh（eta4-cod）} 2（salen）]（1）， [{Rh（eta4-cod）} 2（沙洛芬）]（2），[Rh（（S）-N-苯基氨基乙酸）（eta4-cod）]（3S），[Rh（rac-N-苯基氨基乙酸）（eta4 -cod）]（3rac），[Rh（（R）-N-（4-methoxphenyl）ethyl-2-oxo-1-naphthaldiminato）（eta4-cod）]（4）和[Rh（N-（o- （tolyl）-2-oxo-1-naphthaldiminato）（eta4-cod）]（5）[salen2- = N，N-乙烯-双（sali

  DOI：

  10.1039/b820072f
• 作为产物：
  描述：

  (R)-(+)-1-(4-甲氧基苯)乙胺 、 2-羟基-1-萘甲醛 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以85%的产率得到(R)-N-1-(4-methoxphenyl)ethyl-2-oxo-1-naphthaldimine
  参考文献：
  名称：

  Synthesis, spectroscopy, catalysis and crystal structure of [Rh(η4-cod){(R)-N-(Ar)ethyl-2-oxo-1-naphthaldiminato-κ2N,O}] (Ar=C6H5, 3-/4-MeOC6H4, and 4-BrC6H4)

  摘要：

  Condensation of 2-hydroxy-1-naphthaldehyde with (R)-(Ar) ethylamine yields the enantiopure Schiff bases, (R)-N-(Ar)ethyl-2-hydroxy-1-naphthaldimine (Ar = C6H5, 3-/4-MeOC6H4, 4-BrC6H4). These Schiff bases readily react with the dinuclear complex [Rh(eta(4)-cod)(mu-O2CMe)](2) to afford the mononuclear complexes [Rh(eta(4)-cod){(R)-N-(Ar) ethyl-2-oxo-1-naphthaldiminato-kappa N-2,O}] (Ar = C6H5 (I); 3-MeOC6H4 (II); 4-BrC6H4 (III)), respectively in C6H6/MeOH (5:1, v/v). The Schiff bases and complexes are characterized by IR, UV-Vis, H-1/C-13 NMR and mass spectrometry, polarimetry and HPLC. The polarimetric measurements show the enantiopurity of the Schiff bases as well as the complexes. The X-ray structure determination for III demonstrates that the deprotonated Schiff bases, (R)-N-(Ar) ethyl-2-oxo-1-naphthaldiminate, coordinate to the [Rh(eta(4)-cod)]-fragment as a six-membered N,O-chelate ligand with distorted square planar geometry at the rhodium metal atom. Reaction of III with O-2 leads to the formation of the oxidative aduct [Rh(eta(4)-cod)(mu-O)](2) (IIIa). Compound I or [Rh(eta(4)-cod){(S or R)-N-(phenyl) ethyl-salicylaldiminato}] were used for reduction of acetophenone with diphenylsilane into (+/-)-1-phenyl-ethanol, and conversions up to 93-97% have been achieved. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.01.013

文献信息

• Induced chirality-at-metal and diastereoselectivity at Δ/Λ-configured distorted square-planar copper complexes by enantiopure Schiff base ligands: combined circular dichroism, DFT and X-ray structural studies
  作者：Mohammed Enamullah、A. K. M. Royhan Uddin、Gennaro Pescitelli、Roberto Berardozzi、Gamall Makhloufi、Vera Vasylyeva、Anne-Christine Chamayou、Christoph Janiak

  DOI：10.1039/c3dt52871e

  日期：——

  yield Δ/Λ-chiral four-coordinated, non-planar Cu(N^O)2 complexes [Ar = C6H5R/S-L1, m-C6H4OMe R-L2, p-C6H4OMe R/S-L3, and p-C6H4Br R/S-L4]. Two N,O-chelate ligands coordinate to the copper(II) atom in distorted square-planar mode, and induce metal-centered Δ/Λ-chirality at the copper atom in the C2-symmetric complexes. In the solid state, the R-L1 (or R-L4) ligand chirality diastereoselectively induces a

  对映体纯二齿席夫碱配体，（- [R或小号） - ñ -1-（AR）乙基-2-氧代-1- naphthaldiminato-κ 2 Ñ，ø，非对映选择性得到Δ/Λ手性四配位的，非平面的Cu （N ^ O）2个络合物[Ar = C 6 H 5 R / S -L1，m -C 6 H 4 OMe R -L2，p -C 6 H 4 OMe R / S -L3和p-C 6 H 4 Br R / S -L4 ]。两个N，O-螯合物配体以扭曲的方形平面模式与铜（II）原子配位，并在C 2对称配合物中的铜原子上诱导金属中心的Δ/Λ-手性。在固态下，R -L1（或R -L4）配体手性非对映选择性地诱导Λ-Cu - R -L1（或Λ-Cu- R -L4）中的Λ-Cu构型，S -L1配体aΔ -Δ-Cu-中的-Cu构型S -L1，在结晶时形成对映体纯的晶体。相反地， - [R -L2配体结合了Λ/Δ-CU- ř
• Chirality at metal and helical ligand folding in optical isomers of chiral bis(naphthaldiminato)nickel(<scp>ii</scp>) complexes
  作者：Mohammed Enamullah、Mohammad Abdul Quddus、Mohammad Rezabul Hasan、Gennaro Pescitelli、Roberto Berardozzi、Gamall Makhloufi、Vera Vasylyeva、Christoph Janiak

  DOI：10.1039/c5dt03940a

  日期：——

  Enantiopure bis[(R or S)-N-1-(Ar)ethyl-2-oxo-1-naphthaldiminato-κ2N,O}]nickel(II) complexes Ar = C6H5 (1R or 1S), p-OMeC6H4 (2R or 2S), and p-BrC6H4 (3R or 3S)} are synthesized from the reactions between (R or S)-N-1-(Ar)ethyl-2-oxo-1-naphthaldimine and nickel(II) acetate. Circular-dichroism spectra and their density-functional theoretical simulation reveal the expected mirror image relationship

  对映体纯双[（[R或小号） - ñ -1-（AR）乙基-2-氧代-1- naphthaldiminato-κ 2 Ñ，ö }]镍（II）配合物的Ar = C 6 H ^ 5（1 - [R或1个小号），p -OMeC 6 ħ 4（2 - [R或2小号），和p -BrC 6 ħ 4（3 - [R或3小号）}从（之间的反应合成ř或S）-N -1-（Ar）乙基-2-氧代-1-萘二胺和乙酸镍（II）。圆二色性光谱及其密度泛函理论模拟揭示了溶液中对映体对1 R / 1 S和3 R / 3 S之间的预期镜像关系。CD谱主要由非平面四配位镍的金属中心Λ-或Δ-手性决定，后者又由配体的手性决定。1 R和1 S的单晶结构测定结果表明，每个不对称单元中都有两个不依赖于对称性的分子（A和B），它们的Z '= 2结构。两个不对称且手性的二齿N ^ O-螯合物席夫碱配体与扭曲的方形平面N 2 O 2-配位球中的镍
• Synthesis and Characterization of Bis[(<i>R</i> or <i>S</i>)-<i>N</i>-1-(X-C₆H₄)ethyl-2-oxo-1-naphthaldiminato-κ²<i>N</i>,<i>O</i>]-Λ/Δ-cobalt(II) (X = H, <i>p</i>-CH₃O, <i>p</i>-Br) with Symmetry- and Distance-Dependent Vibrational Circular Dichroism Enhancement and Sign Inversion
  作者：Marcin Górecki、Mohammed Enamullah、Mohammad Ariful Islam、Mohammad Khairul Islam、Simon-Patrick Höfert、Dennis Woschko、Christoph Janiak、Gennaro Pescitelli

  DOI：10.1021/acs.inorgchem.1c01503

  日期：2021.9.20

  The enantiopure Schiff bases (R or S)-N-1-(X-C6H4)ethyl-2-hydroxy-1-naphthaldimine X = H [(R or S)-HL1], p-CH3O [(R or S)-HL2], and p-Br [(R- or S)-HL3]} react with cobalt(II) acetate to give bis[(R or S)-N-1-(X-C6H4)ethyl-2-oxo-1-naphthaldiminato-κ2N,O]-Λ/Δ-cobalt(II) X = H [Λ/Δ-Co-(R or S)-L1], p-CH3O [Λ/Δ-Co-(R or S)-L2], and p-Br [Λ/Δ-Co-(R or S)-L3]} (1–3), respectively. Induced Λ and Δ chirality

  对映体纯席夫碱（R或S）- N -1-(XC 6 H 4 )乙基-2-羟基-1-萘二甲胺X = H [( R或S )-HL1], p -CH 3 O [( R or S )-HL2], 和p -Br [( R - or S )-HL3]} 与乙酸钴(II)反应生成双[( R or S )- N -1-(XC 6 H 4 )乙基-2-氧代-1-萘二氨基-κ 2 N , O ]-Λ/Δ-钴(II) X = H [Λ/Δ-Co-(R或S )-L1]、p- CH 3 O[Λ/Δ-Co-( R或S )-L2]和p- Br[Λ/Δ-Co-( R或S )-L3]}( 1 – 3 )，分别。诱导的 Λ 和 Δ 手性起源于拟四面体几何中C 2对称分子的金属中心。差示扫描量热分析探讨了配合物的热稳定性，1和3经历了从结晶固体到各向同性液相的可逆相变，但2经历了不可逆相变. 像其他钴（II）络合物，化合物1
• Synthesis, X-ray, and Spectroscopic Study of Dissymmetric Tetrahedral Zinc(II) Complexes from Chiral Schiff Base Naphthaldiminate Ligands with Apparent Exception to the ECD Exciton Chirality
  作者：Mohammed Enamullah、Gamall Makhloufi、Rifat Ahmed、Baitul Alif Joy、Mohammad Ariful Islam、Daniele Padula、Howard Hunter、Gennaro Pescitelli、Christoph Janiak

  DOI：10.1021/acs.inorgchem.6b00403

  日期：2016.7.5

  or Δ-chiral-at-metal four-coordinated Zn(R- or S-N^O)2 Ar = C6H5; Zn-1R or Zn-1S and p-C6H4OMe; Zn-2R or Zn-2S}. Two R- or S-N^O-chelate ligands coordinate to the zinc(II) in a tetrahedral mode and induce Λ- or Δ-configuration at the zinc metal center. In the solid state, the R- or S-ligand diastereoselectively gives Λ- or Δ-Zn configuration, respectively, and forms enantiopure crystals. Single crystal

  双齿对映纯席夫碱配体（R或S）-N-1-（Ar）乙基-2-氧代-1-萘二甲酸酯（R-或S -N ^ O），非对映选择性地提供Λ-或Δ-手性金属四配位的Zn（R-或S -N ^ O）2 Ar = C 6 H 5 ; Zn-1 R或Zn-1 S和p -C 6 H 4 OMe；Zn-2 R或Zn-2 S }。两个R-或S-N ^ O-螯合配体以四面体模式与锌（II）配位并在锌金属中心诱导Λ-或Δ-构型。在固态下，R-或S-配体非对映选择性地分别形成Λ-或Δ-Zn构型，并形成对映纯晶体。单晶结构测定显示在每个不对称单元中两个不对称的分子（A和B）给出Z '= 2结构。电子圆二色性（ECD）光谱显示了由非对映异构体过量导致的预期镜像关系，R对配体朝向Λ -Zn，S向Δ-Zn-溶液中的配体。通过TDDFT计算可以很好地再现ECD光谱，而激子手性方法在公共点-偶极近似中的应用预测了长波长对联的错误信号。1
• Synthesis, spectroscopy, catalysis and crystal structure of [Rh(η4-cod){(R)-N-(Ar)ethyl-2-oxo-1-naphthaldiminato-κ2N,O}] (Ar=C6H5, 3-/4-MeOC6H4, and 4-BrC6H4)
  作者：Mohammed Enamullah、A.K.M. Royhan Uddin、Graeme Hogarth、Christoph Janiak

  DOI：10.1016/j.ica.2012.01.013

  日期：2012.5

  Condensation of 2-hydroxy-1-naphthaldehyde with (R)-(Ar) ethylamine yields the enantiopure Schiff bases, (R)-N-(Ar)ethyl-2-hydroxy-1-naphthaldimine (Ar = C6H5, 3-/4-MeOC6H4, 4-BrC6H4). These Schiff bases readily react with the dinuclear complex [Rh(eta(4)-cod)(mu-O2CMe)](2) to afford the mononuclear complexes [Rh(eta(4)-cod)(R)-N-(Ar) ethyl-2-oxo-1-naphthaldiminato-kappa N-2,O}] (Ar = C6H5 (I); 3-MeOC6H4 (II); 4-BrC6H4 (III)), respectively in C6H6/MeOH (5:1, v/v). The Schiff bases and complexes are characterized by IR, UV-Vis, H-1/C-13 NMR and mass spectrometry, polarimetry and HPLC. The polarimetric measurements show the enantiopurity of the Schiff bases as well as the complexes. The X-ray structure determination for III demonstrates that the deprotonated Schiff bases, (R)-N-(Ar) ethyl-2-oxo-1-naphthaldiminate, coordinate to the [Rh(eta(4)-cod)]-fragment as a six-membered N,O-chelate ligand with distorted square planar geometry at the rhodium metal atom. Reaction of III with O-2 leads to the formation of the oxidative aduct [Rh(eta(4)-cod)(mu-O)](2) (IIIa). Compound I or [Rh(eta(4)-cod)(S or R)-N-(phenyl) ethyl-salicylaldiminato}] were used for reduction of acetophenone with diphenylsilane into (+/-)-1-phenyl-ethanol, and conversions up to 93-97% have been achieved. (C) 2012 Elsevier B. V. All rights reserved.