(1R,2R)-N,N'-bis(3-phenylsalicyl)cyclohexane-1,2-diamine | 902779-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R)-N,N'-bis(3-phenylsalicyl)cyclohexane-1,2-diamine
• 英文别名: (1R,2R)-N,N’-di[(2-hydroxy-3-phenyl)benzyl]-1,2-diaminocyclohexane；H₂((NH)₂salhexPh₂)；THG 1213；2-[[[(1R,2R)-2-[(2-hydroxy-3-phenylphenyl)methylamino]cyclohexyl]amino]methyl]-6-phenylphenol
• CAS: 902779-56-0
• 化学式: C₃₂H₃₄N₂O₂
• 分子量: 478.634
• InChiKey: VULDRYBWNMXMBZ-LOYHVIPDSA-N

物化性质

• 沸点：
  646.4±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  64.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-N,N'-bis(3-phenylsalicyl)cyclohexane-1,2-diamine 、 zinc(II) acetate dihydrate 以 甲醇 为溶剂， 反应 16.0h， 以70%的产率得到[((NH₂)salhexPh₂)Zn]
  参考文献：
  名称：

  Redox chemistry of copper complexes with various salen type ligands

  摘要：

  The two essential redox processes in Cu(II) salen (and salan) complexes Cu(II)/Cu(I) and [PhO](center dot)/[PhO[-]] were studied by electrochemical and spectroelectrochemical (UV-Vis-absorption or EPR) techniques on a series of complexes in which the salen (salan) type ligands bear various substituents R = H, F, Ph, tBu or CH3 on the linker C- or N-atoms or on the phenol core. The substitution pattern can be related to the stability of the phenoxy radicals. The geometry of the complexes (especially around the Cu atom) could be established by XRD for the new complex [(Me(2)salhexF(4))Cu] {H-2(Me(2)salhexF(4)) = (1R,2R)-N,N'-bis(2-hydroxy-3,5-di-fluoro-acetophenonylidene)-cyclohexane-1,2-diamine} in the solid and for all other derivatives by EPR in fluid solution. Also, the application of the complexes in oxidation catalysis was tested using the oxidation of benzyl alcohol. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.08.016
• 作为产物：
  描述：

  (1R,2R)-N,N′-bis(3-phenylsalicylidene)-1,2-cyclohexanediamine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以74%的产率得到(1R,2R)-N,N'-bis(3-phenylsalicyl)cyclohexane-1,2-diamine
  参考文献：
  名称：

  Redox chemistry of copper complexes with various salen type ligands

  摘要：

  The two essential redox processes in Cu(II) salen (and salan) complexes Cu(II)/Cu(I) and [PhO](center dot)/[PhO[-]] were studied by electrochemical and spectroelectrochemical (UV-Vis-absorption or EPR) techniques on a series of complexes in which the salen (salan) type ligands bear various substituents R = H, F, Ph, tBu or CH3 on the linker C- or N-atoms or on the phenol core. The substitution pattern can be related to the stability of the phenoxy radicals. The geometry of the complexes (especially around the Cu atom) could be established by XRD for the new complex [(Me(2)salhexF(4))Cu] {H-2(Me(2)salhexF(4)) = (1R,2R)-N,N'-bis(2-hydroxy-3,5-di-fluoro-acetophenonylidene)-cyclohexane-1,2-diamine} in the solid and for all other derivatives by EPR in fluid solution. Also, the application of the complexes in oxidation catalysis was tested using the oxidation of benzyl alcohol. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.08.016
• 作为试剂：
  描述：

  (3-丁炔-1-基氧基)(2-甲基-2-丙基)二苯基硅烷 在 咪唑 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 (1R,2R)-N,N'-bis(3-phenylsalicyl)cyclohexane-1,2-diamine 、 双氧水 、 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 31.33h， 生成 tert-butyl-[4-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]but-3-ynoxy]-diphenylsilane
  参考文献：
  名称：

  莱奥多利德B拼图

  摘要：

  别无选择了吗？尽管选择了一种系统的方法，导致围绕拟议的莱奥多利德B结构（参见图片）建模了四个非对映体大环内酯类化合物，但有关这种源自深海海绵的细胞毒性代谢物的立体结构的难题仍未解决。

  DOI：

  10.1002/anie.201005850

文献信息

• Titanium Salan Catalysts for the Asymmetric Epoxidation of Alkenes: Steric and Electronic Factors Governing the Activity and Enantioselectivity
  作者：Evgenii P. Talsi、Denis G. Samsonenko、Konstantin P. Bryliakov

  DOI：10.1002/chem.201404157

  日期：2014.10.27

  A new insight into the highly enantioselective (up to >99.5 % ee) epoxidation of olefins in the presence of chiral titanium(IV) salan complexes is reported. A series of 14 chiral ligands with varying steric and electronic properties have been designed, and it was found that electronic effects modulate the catalytic activity (without affecting the enantioselectivity), whereas the steric properties account

  报道了在手性钛（IV）salan络合物存在下烯烃的高度对映选择性（高达> 99.5％ee）环氧化的新见解。已经设计了一系列具有变化的空间和电子性质的14种手性配体，并且发现电子效应调节催化活性（不影响对映选择性），而空间性质解释了环氧化的对映选择性。对位取代苯乙烯的竞争性氧化揭示了氧转移活性物质的亲电子性质，哈米特ρ值为-0.51；对映选择性不受p的给电子（或撤离）能力的影响取代基。机理研究提供了有利于逐步反应机理的证据：在第一阶段（速率确定），烯烃最有可能与活性物质配位，然后进行分子内对映选择性氧转移。对映选择性随温度降低而增加。经修饰的Eyring曲线为苯乙烯的环氧化和（Ž）-β -甲基苯乙烯是线性的，表示立体选择性的一个单一的，焓控制机构，用ΔΔ ħ ≠ = -6.6千焦耳摩尔-1和-5.4千焦耳摩尔-1，分别。
• Ti-Salan catalyzed asymmetric sulfoxidation of pyridylmethylthiobenzimidazoles to optically pure proton pump inhibitors
  作者：Evgenii P. Talsi、Konstantin P. Bryliakov

  DOI：10.1016/j.cattod.2016.03.006

  日期：2017.1

  Abstract The asymmetric sulfoxidation of two pyridylmethylthiobenzimidazoles to anti-ulcer drugs of the PPI family ( S )-omeprazole and ( R )-lansoprazole with hydrogen peroxide, mediated by a series of chiral titanium(IV) salan complexes is reported. High sulfoxide yields (up to >95%) and enantioselectivities (up to 94% ee ) have been achieved. The introduction of electron-withdrawing substituents

  摘要 报道了由一系列手性钛（IV）salan 配合物介导的过氧化氢对两种吡啶基甲基硫代苯并咪唑的不对称磺化氧化为PPI 家族（S）-奥美拉唑和（R）-兰索拉唑的抗溃疡药物。已经实现了高亚砜产率（高达 >95%）和对映选择性（高达 94% ee）。吸电子取代基的引入导致催化剂活性降低和对映选择性降低。与先前报道的 Ti-salalen 催化的磺化氧化一样，在 Ti-salan 配合物存在下，磺化氧化对映选择性对温度的依赖性是非单调的，表明随着温度的降低具有同相转化行为。氧化可能受到活性物质（可能是过氧钛（IV））形成的限制，
• PROCESS FOR PRODUCING OPTICALLY ACTIVE EPOXY COMPOUND, COMPLEX FOR USE IN THE PROCESS, AND PROCESS FOR PRODUCING THE SAME
  申请人：Japan Science and Technology Agency

  公开号：EP1849778B1

  公开（公告）日：2013-04-24
• Method for Production of Optically Active Epoxy Compound, and Complex Used Therefor and Process for Producing the Same
  申请人：Katsuki Tsutomu

  公开号：US20080071099A1

  公开（公告）日：2008-03-20

  There is provided a method for industrially producing optically active epoxy compounds by asymmetrically epoxidizing prochiral unsaturated compounds with an oxidant using as a catalyst a single substance or a di-μ-oxo dimer derived therefrom represented by any of the following formulae (I), (I′), (II), (II′), (III), (III′), (IV), and (IV′): [wherein R 1 s are independently an alkyl group or an aryl group; R 2 s are independently an alkyl group or an aryl group; R 3 s are independently an alkyl group or an aryl group, provided that two R 3 s may be bonded with each other to form a ring; R 4 s are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, or a cyano group; M is TiY 2 (Y is Cl, alkoxide, or a μ-oxo ligand)].
• METHOD FOR PRODUCTION OF OPTICALLY ACTIVE EPOXY COMPOUND, AND COMPLEX USED THEREFOR AND PROCESS FOR PRODUCING THE SAME
  申请人：KATSUKI Tsutomu

  公开号：US20120178954A1

  公开（公告）日：2012-07-12

  A complex, and a process for producing the same, represented by any of the following formulae (I), (I′), (II), (II′), (III), (III′), (IV), and (IV′): where: R 1 s are independently an alkyl group or an aryl group; R 2 s are independently a hydrogen atom, an alkyl group, or an aryl group; R 3 s are independently an alkyl group or an aryl group, provided that two R 3 s are optionally bonded with each other to form a ring; R 4 s are independently a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a nitro group, or a cyano group; and M is TiY 2 , where Y is Cl or alkoxide or the complex forms a di-μ-oxo dimer where Y is a μ-oxo ligand.