2,2'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)diphenol | 215057-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,2'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)diphenol
• 英文别名: (1R,2R)--1,2-diaminocyclohexane；(1R,2R)-bis(salicylaldehyde)-trans-cyclohexylidiamine；(R,R)-N,N'-bis-salicylidene-1,2-cyclohexanediamine；(R,R)-N,N'-bissalicylidene-1,2-diaminocyclohexane；trans-(R,R)-1,2-Bis(salicylideneamino)cyclohexane；N,N'-(1,2-cyclohexylene)bis(salicylideneimine)
• CAS: 215057-24-2
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: WCSLPBBQHFXWBW-BGSCIDCASA-N

物化性质

• 沸点：
  515.6±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.18
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)diphenol 在 甲烷磺酸 、 四乙基对甲苯磺酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到2-[(2S,3S,4aR,8aR)-3-(2-hydroxyphenyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroquinoxalin-2-yl]phenol
  参考文献：
  名称：

  Electroorganic chemistry. 129. Electroreductive synthesis of chiral piperazines and enantioselective addition of diethylzinc to aldehydes in the presence of the chiral piperazines

  摘要：

  Electroreduction of diimines, prepared from 1,2-diamines and aromatic aldehydes, in acidic media gave intramolecularly coupled products, 2,3-diarylpiperazines, stereoselectively. Chiral tri- and tetrasubstituted piperazines were synthesized effectively from chiral 1,2-diamines by the same electroreductive method. Chiral piperazines, prepared from 1(R),2(R)-diaminocyclohexane were effective chiral ligands of catalysts for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00009a026
• 作为产物：
  描述：

  邻甲基苄醇 、 (R,R)-1,2-diaminocyclohexane tartrate 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以80%的产率得到2,2'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)diphenol
  参考文献：
  名称：

  Aluminium–SALEN complex: a new catalyst for the enantioselective Michael reaction

  摘要：

  A new heterobimetallic complex prepared from a chiral SALEM ligand and Red-Al-(R) was found to catalyse the Michael reaction between various dialkyl malonates and cycloalkenones to give products in high yields with e.e.s of up to 58%. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00433-5
• 作为试剂：
  描述：

  1-甲基吲哚 、 麦锈灵 、 苯乙炔 在 copper(l) iodide 、 2,2'-(1E,1'E)-(1R,2R)-cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-ylidene)diphenol 、 三乙胺 作用下， 以 水 为溶剂， 以78%的产率得到3-benzyl-3-(1-methyl-1-H-indol-3-yl)-2-phenylisoindolin-1-one
  参考文献：
  名称：

  在水性胶束系统中通过简单方便的MCR有效合成3-苄基-3-（吲哚-3-基）-2-苯基-2,3-二氢异吲哚满酮衍生物

  摘要：

  通过涉及2-碘-N-苯基苯甲酰胺的多组分一锅反应，开发了一种环境友好且操作简单的方法来合成3-苄基-3-（吲哚-3-基）-2-苯基-2,3-二氢异吲哚满酮，末端炔烃和胶束介质水溶液中的取代的吲哚。它涉及使用CuI作为催化剂和2,2'-（1 E，1'E）-（1）铜介导的多米诺骨牌Sonogashira-5-exo-dig-环化反应，然后在一个锅中对吲哚进行区域选择性亲核加成。在好氧条件下，以R，2 R）-环己烷-1,2-二基双（氮杂-1-基-1-亚烷基）双（甲基-1-基-1-亚烷基）二酚为配体。

  DOI：

  10.1016/j.tetlet.2013.05.151

文献信息

• Efficient Asymmetric Oxidation of Sulfides and Kinetic Resolution of Sulfoxides Catalyzed by a Vanadium−Salan System
  作者：Jiangtao Sun、Chengjian Zhu、Zhenya Dai、Minghua Yang、Yi Pan、Hongwen Hu

  DOI：10.1021/jo040221d

  日期：2004.11.1

  The asymmetric oxidation of sulfides to chiral sulfoxides with hydrogen peroxide in good yield and high enantioselectivity has been catalyzed very effectively by chiral vanadium−salan [N,N‘-alkyl bis(salicylamine)] complex. The salan ligand shows results superior in terms of reactivity and enantioselectivity to those of salen [N,N‘-alkylene bis(salicylideneimine)] analogue, and provides the sulfoxide

  硫化钒以高收率和高对映选择性将硫化物不对称氧化为手性亚砜已被手性钒-Salan [ N，N'-烷基双（水杨胺）]络合物非常有效地催化。所述salan配体在反应性和对映选择性方面显示出优于salen [ N，N′-亚烷基双（水杨亚基亚胺）]类似物的结果，并提供具有相反构型的亚砜。该反应的高对映选择性是不对称氧化的直接结果。还描述了钒-salan系统催化的外消旋亚砜的有效动力学拆分。
• AFM study of a New Carrier Based on PLA and Salen Copolymers for Gene Therapy
  作者：V. Nadeau、P. Hildgen

  DOI：10.3390/10010105

  日期：——

  The aim of this study was to synthesize novel biodegradable charged polymers to be used in DNA complexation for genetic delivery in different diseases. A new copolymer of PLA and complexed Schiff bases was synthesized in a several steps. This copolymer will be used as a nanocarrier. Also, AFM comparative studies in tapping mode were performed; on cationic copolymer and on PLA-Schiff base copolymer, on non-oriented and oriented film and on the DNA-cationic complex. The results indicated a difference in the topology and on phase picture of AFM film with or without cationic charge.

  本研究的目的是合成新型可生物降解带电聚合物，用于 DNA 复合物在不同疾病中的基因传递。通过几个步骤合成了聚乳酸和络合希夫碱的新型共聚物。这种共聚物将用作纳米载体。此外，还对阳离子共聚物和聚乳酸-席夫碱共聚物、无取向薄膜和取向薄膜以及 DNA 阳离子复合物进行了攻丝模式原子力显微镜比较研究。结果表明，带阳离子电荷和不带阳离子电荷的原子力显微镜薄膜在拓扑结构和相图上存在差异。
• [EN] MONONUCLEAR SALEN INDIUM CATALYSTS AND METHODS OF MANUFACTURE AND USE THEREOF<br/>[FR] CATALYSEURS MONONUCLÉAIRES D'INDIUM DE SALEN ET LEURS MÉTHODES DE PRODUCTION
  申请人：UNIV BRITISH COLUMBIA

  公开号：WO2016000071A1

  公开（公告）日：2016-01-07

  The present application provides salen indium catalysts of the following general structure wherein R is a coordinating alkoxide comprising at least one coordinating atom that forms a dative bond with In. The mononuclear salen indium catalysts are particularly useful in catalyzing ring-opening polymerizations of cyclic ester monomers, such as lactides. Also provided herein are methods of using the mononuclear salen indium complexes to catalyze polymerization of cyclic ester monomers. Of particular interest is the successful polymerization of lactides using the mononuclear salen indium catalysts to produce poly(lactic acid) having high isotacticity.

  本申请提供了以下一般结构的salen铟催化剂，其中R是一个包含至少一个与铟形成配位键的配位氧化物。这些单核salen铟催化剂在催化环酯单体的开环聚合中特别有用，例如内酯。本文还提供了使用单核salen铟配合物催化环酯单体聚合的方法。特别值得关注的是使用单核salen铟催化剂成功聚合内酯，生产具有高同构度的聚乳酸。
• Substituted salen–Ru(II) complexes as catalysts in the asymmetric cyclopropanation of styrene by ethyl diazoacetate: the influence of substituents and achiral additives on activity and enantioselectivity
  作者：Xiaoquan Yao、Min Qiu、Weiran Lü、Huilin Chen、Zhuo Zheng

  DOI：10.1016/s0957-4166(01)00014-3

  日期：2001.2

  asymmetric cyclopropanation of styrene with ethyl diazoacetate by its ruthenium(II) complex with [RuCl2(p-cymene)]2 or RuCl2(PPh3)3 as precursors. The introduction of appropriate electron withdrawing groups in the salen ligands benefited the enantioselectivity of the reaction. Some additives, including O-donor, N-donor and P-donor ligands, were added to the reaction to improve the enantioselectivity and

  一系列烷基，卤素和硝基取代的Salen配体1已通过重氮钌与[RuCl 2（p- cymene）] 2或RuCl 2的钌（II）络合物用于苯乙烯与重氮乙酸乙酯的不对称环丙烷化中。（PPh 3）3作为前体。在萨伦配体中引入合适的吸电子基团有利于反应的对映选择性。将一些添加剂，包括O-供体，N-供体和P-供体配体添加到反应中，以提高对映选择性和活性，并获得高达80％的ee。在salen / [RuCl 2（p- cymene）] 2体系，通过使用衍生自Et 3 N的3，5-二溴化水杨醛衍生的salen配体1f，在80.2％ee中获得（1 R，2 S）-异构体。通过使用由硝基取代的配体1m和RuCl 2（PPh 3）3合成的配合物2，可以实现（1 S，2 R）异构体的最高81.3％的Ees 。还讨论了一种可能的机制。
• [EN] SALEN INDIUM CATALYSTS AND METHODS OF MANUFACTURE AND USE THEREOF<br/>[FR] CATALYSEURS D'INDIUM DE SALEN ET PROCÉDÉS DE FABRICATION ASSOCIÉS
  申请人：GREENCT CANADA

  公开号：WO2013134877A1

  公开（公告）日：2013-09-19

  The present application provides salen indium catalysts of the following general structure (Formula (I)), and the corresponding dimers. The salen indium catalysts are particularly useful in catalyzing ring-opening polymerizations of cyclic ester monomers, such as lactides. Also provided herein are methods of using the salen indium complexes to catalyze polymerization of cyclic ester monomers. Of particular interest is the successful polymerization of lactides using the present salen indium catalysts to produce poly(lactic acid) having high isotacticity.

  本申请提供以下一般结构（公式（I））的萨林铟催化剂及其相应的二聚体。萨林铟催化剂在催化环酯单体的开环聚合中特别有用，例如乳酸内酯。本文还提供使用萨林铟配合物催化环酯单体聚合的方法。尤其值得关注的是，使用本申请的萨林铟催化剂成功聚合乳酸内酯，产生具有高同形异构度的聚乳酸。