(S,S)-N,N′-bis-(3-methoxysalicylidene)cyclohexane-1,2-diamine | 177898-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S,S)-N,N′-bis-(3-methoxysalicylidene)cyclohexane-1,2-diamine
• 英文别名: (S,S)-(N,N'-bis(3-methoxysalicylidene)cyclohexane-1,2-diamine)；N,N'-bis(3-methoxysalicylidene)-(S,S')-1,2-cyclohexanediamine；(1S,2S)-[N,N’-bis(2’-hydroxy-3’-methoxybenzylidene)]-1,2-diaminocyclohexane；N,N'-bis(3-methoxy-2-hydroxy-1-benzylidene)-1S,2S-cyclohexanediamine；trans-N,N'-Bis(3-methoxysalicylidene)-1,2-cyclohexanediamine；2-[[(1S,2S)-2-[(2-hydroxy-3-methoxyphenyl)methylideneamino]cyclohexyl]iminomethyl]-6-methoxyphenol
• CAS: 177898-70-3
• 化学式: C₂₂H₂₆N₂O₄
• 分子量: 382.459
• InChiKey: ZKNAXCMGWQHLTL-ROUUACIJSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  565.5±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S,S)-N,N′-bis-(3-methoxysalicylidene)cyclohexane-1,2-diamine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 以97%的产率得到cyclohexane-1,2-diylbis(azanediyl)bis(methylene)bis(2-methoxyphenol)
  参考文献：
  名称：

  Dinuclear Zinc Salen Catalysts for the Ring Opening Copolymerization of Epoxides and Carbon Dioxide or Anhydrides

  摘要：

  A series of four dizinc complexes coordinated by salen or salan ligands, derived from ortho-vanillin and bearing (+/-)-trans-1,2-diarninocyclohexane (L-1) or 2,2-climethyl-1,3-pro-panediamine (L-2) backbones, is repotted. The complexes are characterized using a combination of X-ray crystallography, rnultinudear NMR, DOSY, and MALDI-TOF Spectroscopies, and elemental analysis. The stability of the- dinudeat complexes depends on the ligand structure) with the most stable complexes having imine substituents. The complexes are tested as catalysts for the ring-opening copolymerization (ROCOP) of CO2/cyclohexene oxide (CHO) and phthalie anhydride (PA)/CHO. All complexes are active, and the structure/activity relationships reveal that the complex having both L-2 and imine substituents displays the highest activity. In the ROCOP of CO2/CHO its activity is equivalent to other metal salen catalysts (TOP = 44 h(-1) at a catalyst loading of 0.1 mol %, 30 bar of CO2, and 80 degrees C), while for the ROCOP of PA/CHO, its activity is slightly higher than other metal salen catalysts (TOP = 198 h(-1) at a catalyst loading of 1 mol % and 100 degrees C). Poly(ester-block-carbonate) polymers are also afforded using the most active catalyst by the one-pot terpolymerization of PA/CHO/CO2.

  DOI：

  10.1021/acs.inorgchem.5b02233
• 作为产物：
  描述：

  邻香草醛 、 trans-1,2-Diaminocyclohexane 以 甲醇 为溶剂， 反应 4.0h， 以100%的产率得到(S,S)-N,N′-bis-(3-methoxysalicylidene)cyclohexane-1,2-diamine
  参考文献：
  名称：

  Dinuclear Zinc Salen Catalysts for the Ring Opening Copolymerization of Epoxides and Carbon Dioxide or Anhydrides

  摘要：

  A series of four dizinc complexes coordinated by salen or salan ligands, derived from ortho-vanillin and bearing (+/-)-trans-1,2-diarninocyclohexane (L-1) or 2,2-climethyl-1,3-pro-panediamine (L-2) backbones, is repotted. The complexes are characterized using a combination of X-ray crystallography, rnultinudear NMR, DOSY, and MALDI-TOF Spectroscopies, and elemental analysis. The stability of the- dinudeat complexes depends on the ligand structure) with the most stable complexes having imine substituents. The complexes are tested as catalysts for the ring-opening copolymerization (ROCOP) of CO2/cyclohexene oxide (CHO) and phthalie anhydride (PA)/CHO. All complexes are active, and the structure/activity relationships reveal that the complex having both L-2 and imine substituents displays the highest activity. In the ROCOP of CO2/CHO its activity is equivalent to other metal salen catalysts (TOP = 44 h(-1) at a catalyst loading of 0.1 mol %, 30 bar of CO2, and 80 degrees C), while for the ROCOP of PA/CHO, its activity is slightly higher than other metal salen catalysts (TOP = 198 h(-1) at a catalyst loading of 1 mol % and 100 degrees C). Poly(ester-block-carbonate) polymers are also afforded using the most active catalyst by the one-pot terpolymerization of PA/CHO/CO2.

  DOI：

  10.1021/acs.inorgchem.5b02233

文献信息

• Synthesis, Characterization, and <i>In Vitro</i> Cytotoxicity of Platinum(II) Complexes Bearing Chiral Tetradentate Salicylaldimine Ligands
  作者：Quang Trung Nguyen、Phuong Nam Pham Thi、Van Tuyen Nguyen

  DOI：10.1155/2020/5414959

  日期：2020.6.16

  A series of platinum(II) complexes with chiral Schiff base ligands derived from various salicylaldehydes with (R,R′)- and (S,S′)-cyclohexanediamine were synthesized and characterized by ESI-MS, IR, and NMR. Obtained spectra with typical signals were in agreement with suggested molecular formulae of the complexes. Their photophysical properties were studied by UV-visible and emission spectroscopies

  合成了一系列具有手性席夫碱配体的铂 (II) 配合物，这些配体来源于各种水杨醛与 (R,R')- 和 (S,S')-环己二胺，并通过 ESI-MS、IR 和 NMR 进行表征。获得的具有典型信号的光谱与建议的复合物分子式一致。通过紫外-可见光和发射光谱研究了它们的光物理特性。UV-Vis 显示 MLCT 在可见光范围 400-500 nm 处的典型低能量波段，该波段可以发射最大发射波长为 529-595 nm 的发光波段。针对 KB 和 MCF-7 人类癌细胞系筛选了获得的铂 (II) 复合物的体外细胞毒性。
• Synthesis, Characterization, and Application of Vanadium−Salan Complexes in Oxygen Transfer Reactions
  作者：Pedro Adão、João Costa Pessoa、Rui T. Henriques、Maxim L. Kuznetsov、Fernando Avecilla、Mannar R. Maurya、Umesh Kumar、Isabel Correia

  DOI：10.1021/ic8017985

  日期：2009.4.20

  We report the synthesis and characterization of several chiral salen- and salan-type ligands and their vanadium complexes, which are derived from salicylaldehyde or salicylaldehyde derivatives and chiral diamines (1R,2R-diaminocyclohexane, 1S,2S-diaminocyclohexane, and 1S,2S-diphenylethylenediamine). The structures of H2sal(R,R-chan)2+·2Cl−·(CH3)2CHOH·H2O (1c; H2sal(R,R-chan) = N,N′-salicyl-R,R-cyclohexanediaminium)

  我们报告了合成和表征的几种手性SAlen和SAlan型配体及其钒配合物，它们衍生自水杨醛或水杨醛衍生物和手性二胺（1 R，2 R-二氨基环己烷，1 S，2 S-二氨基环己烷和1 S，2 S-二苯基乙二胺）。H的结构2 SAL（[R， - [R -chan）2+ ·2CL - ·（CH 3）2 CHOH·H 2 O（1C H; 2 SAL（[R， - [R-chan）= N，N'-水杨基-R，R-环己烷二铵），Etvan（S，S -chen）（3c ; Etvan（S，S -chen）= N，N'-3-乙氧基-水杨基-S，S-环己烷二亚胺基）和naph （R，R -chen）（6c ; naph （R，R -chen）= N，N'-萘叉-R，R-环己烷二亚氨基）通过单晶X射线衍射测定。制备了相应的钒（IV）配合物和涉及不同水杨醛型前体的其他几种新配合物，并通过光谱技术在固态和溶液中进行了表征
• Inclusion complexes of sodium perchlorate into [CuLSS] and [CuLrac]; H2LSS = bis(3-methoxy-2-hydroxy-1-benzylidene)-1S,2S-cyclohexanediamine, H2Lrac = its racemic form
  作者：Takeshi Fujinami、Ryuichi Kinoshita、Hirokazu Kawashima、Naohide Matsumoto、Jack H. Harrowfield、Yang Kim

  DOI：10.1007/s10847-011-9980-z

  日期：2011.12

  Inclusion complexes of LiClO4 or NaClO4 into [CuLSS] or [CuLrac] are reported, where [CuLSS] denotes bis(3-methoxy-2-oxy-1-benzylidene)-1S,2S-cyclohexanediaminecopper(II) and [CuLrac] denotes the racemic complex. The inclusion reaction of LiClO4 and NaClO4 into [CuLSS] gave the [1 + 1] adduct of [CuLSS(H2O)LiClO4] and the [2 + 1] adduct of [(CuLSS)2Na(H2O)3]ClO4, respectively, while that of NaClO4 into [CuLrac] gave the [2 + 2] adduct of [CuLracNaClO4]2·CH3CN ([(CuLSSNaClO4)(CuLRRNaClO4)]·CH3CN). Reaction of NaClO4 and [CuLSS] gave the [2 + 1] adduct [(CuLSS)2Na(H2O)3]ClO4, while the reaction of NaClO4 and the racemic complex [CuLrac] gave the [2 + 2] adduct [CuLracNaClO4]2, where [CuLSS] denotes bis(3-methoxy-2-oxy-1-benzylidene)-1S,2S-cyclohexanediaminecopper(II).

  报道了LiClO4或NaClO4与[CuLSS]或[CuLrac]的包合物，其中[CuLSS]表示双(3-甲氧基-2-氧基-1-亚苄基)-1S,2S-环己烷二胺铜(II)，[CuLrac]表示外消旋复合物。 LiClO4 和 NaClO4 与 [CuLSS] 发生包合反应，分别得到 [CuLSS(H2O)LiClO4] 的 [1 + 1] 加合物和 [(CuLSS)2Na( )3]ClO4 的 [2 + 1] 加合物，将 NaClO4 加入到 [CuLrac] 中，得到 [CuLracNaClO4]2·CH3CN ([(CuLSSNaClO4)(CuLRRNaClO4)]·CH3CN 的 [2 + 2] 加合物。 NaClO4 和 [CuLSS] 反应得到 [2 + 1] 加合物 [(CuLSS)2Na( )3]ClO4，而 NaClO4 和外消旋络合物 [CuLrac] 反应得到 [2 + 2] 加合物 [CuLracNaClO4] 2，其中[CuLSS]表示双(3-甲氧基-2-氧基-1-亚苯亚基)-1S,2S-环己烷二胺铜(II)。
• Enantioselective Cobalt-Catalyzed Preparation of Trifluoromethyl-Substituted Cyclopropanes
  作者：Bill Morandi、Brian Mariampillai、Erick M. Carreira

  DOI：10.1002/anie.201004269

  日期：2011.2.1

  Easy access on water: A cobalt‐catalyzed asymmetric preparation of trifluoromethylcyclopropanes has been developed that yields high enantioselectivities with a broad range of styrene substrates (see scheme). The reaction presents a new access to enantioenriched CF3‐containing building blocks.

  易于在水上获取：已开发出钴催化的三氟甲基环丙烷的不对称制备物，可在广泛的苯乙烯底物范围内产生高对映选择性（请参见方案）。该反应为获得富含对映体的CF 3的构建基块提供了新途径。
• A pair of chiral Cu( <scp>II</scp> )‐Tb( <scp>III</scp> )‐Fe( <scp>III</scp> ) heterotrimetallic enantiomers: Structural, luminescent, and magnetic studies
  作者：Zi‐Xuan Wang、Ya‐Nan Yuan、Qing‐Lun Wang、Qi Wang、Xiang‐Jian Meng、Chun Yang

  DOI：10.1002/jccs.202100228

  日期：2021.11

  [Cu(H2O)(R,R)-valcy}Tb(CH3OH)2(H2O)(μ-CN)Fe(CN)5]·[Cu(H2O)(R,R)-valcy}Tb(CH3OH)1.5(H2O)1.5(μ-CN)Fe(CN)5]·7.85H2O·2CH3OH (1) (H2(R,R)-valcy = N,N′-bis(3-methoxysalicylidene)-1R,2R-1,2-diaminocyclohexane), has been prepared and structurally characterized by X-ray single-crystal diffraction. In 1, the asymmetric trinuclear CuIITbIIIFeIII} units are assembled into 1-D supramolecular single chain by hydrogen-bonds

  一种手性异三金属化合物，[Cu(H 2 O)( R,R )-valcy}Tb(CH 3 OH) 2 (H 2 O)( μ -CN)Fe(CN) 5 ]·[Cu(H 2 O)( R,R )-价}Tb(CH 3 OH) 1.5 (H 2 O) 1.5 ( μ -CN)Fe(CN) 5 ]·7.85H 2 O·2CH 3 OH ( 1 ) (H 2 ( R,R )-valcy = N,N' -双(3-甲氧基水杨 基)- 1R,2R-1,2-二氨基环己烷），已通过 X 射线单晶衍射进行制备和结构表征。图1中，不对称三核Cu II Tb III Fe III }单元通过氢键组装成一维超分子单链，超分子链进一步连接成二维片。磁性研究显示整体弱铁磁相互作用和磁各向异性。1的对映异构体，表示为配合物2，衍生自 N,N' -双（3-甲氧基水杨烯）- 1S,2S还合成了-1,2-二氨基环己烷，并通过PXRD、红外光谱、CD