(1R,2R)-1-(1',8'-naphthalimido)-2-aminocyclohexane | 593284-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (1R,2R)-1-(1',8'-naphthalimido)-2-aminocyclohexane
• 英文别名: 2-[(1R,2R)-2-aminocyclohexyl]benzo[de]isoquinoline-1,3-dione
• CAS: 593284-22-1
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: FJWUBHUIAVCNSG-HUUCEWRRSA-N

物化性质

• 熔点：
  205-210 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  484.8±38.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  均苯四甲酸二酐 、 (1R,2R)-1-(1',8'-naphthalimido)-2-aminocyclohexane 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以13%的产率得到
  参考文献：
  名称：

  Solvent induced folding of conformationally bistable helical imide triads

  摘要：

  Foldamer population of imide triads derived from (R,R)-1,2-diaminocyclohexane was studied with the use of H-1 NMR and CD spectroscopy, as well as computational modeling. Two stable foldamers of C and S shape, having correspondingly M and P helicity, are found to differ very little in energy. However, their interaction with the solvent results in significant shift of the equilibrium. For the interaction with aromatic solvent molecules a sandwich-type donor-acceptor model, stabilizing the S foldamer, is proposed. The limitations of the NMR and CD methods for studying the foldamer equilibrium in solution are discussed, pointing to the inadequacy of static computational models of CD spectra, not including the effect of rotation of the imide chromophores in the dynamic model of real molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.039
• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(1R,2R)-1-(1',8'-naphthalimido)-2-aminocyclohexane
  参考文献：
  名称：

  Facile monoprotection of trans-1,2-diaminocyclohexane

  摘要：

  A new method of monoprotection of C-2-symmetric trans-1,2-diaminocyclohexane as the N-phthaloyl, N-tetrachlorophthaloyl or N-1,8-naphthaloyl derivative is presented. The first two derivatives are obtained with high yields and can be readily transformed into other unsymmetrical derivatives of trans-1,2-diaminocyclohexane. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00308-2
• 作为试剂：
  描述：

  2-甲基戊醛 、 偶氮二甲酸二苄酯 在 三氟乙酸 、 (1R,2R)-1-(1',8'-naphthalimido)-2-aminocyclohexane 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以57%的产率得到
  参考文献：
  名称：

  第四立体中心的构建：单酰亚胺取代的环己烷-1，2-二胺催化的支链醛的不对称α-胺化

  摘要：

  据报道，由手性酰亚胺单取代的1,2-二胺衍生物催化的支链醛类的高效对映选择性α-胺化可提供优良的产率（高达99％）和对映选择性（高达ee的97％）的四级立体异构中心。手性25：668–672，2013年。©2013 Wiley Periodicals，Inc

  DOI：

  10.1002/chir.22203

文献信息

• A Highly Efficient Large-Scale Asymmetric Direct Intermolecular Aldol Reaction Employing L-Prolinamide as a Recoverable Catalyst
  作者：Yang Yang、Yan-Hong He、Zhi Guan、Wei-Da Huang

  DOI：10.1002/adsc.201000355

  日期：2010.10.4

  A new, simple bifunctional, recoverable and reusable L-prolinamide organocatalyst that promotes aldol reactions while achieving a respectable level of enantioselectivity is reported. This organocatalyst is applicable to the reactions of a wide range of aromatic and heteroaromatic aldehydes with cyclic and acyclic ketones, and the anti-aldol products could be obtained with up to 99:1 anti/syn ratio

  报道了一种新型的，简单的双功能，可回收和可重复使用的L-脯氨酰胺有机催化剂，该催化剂可促进醛醇缩合反应，同时达到可观的对映选择性。该有机催化剂适用于多种芳族和杂芳族醛与环状和无环酮的反应，可以以高达99：1的抗/合成比和98％ee的抗醛产物获得。该催化剂可以容易地回收和再利用，并且在五个循环中仅观察到对映选择性的轻微降低。该新型催化剂可以有效地用于大规模反应，同时将对映选择性保持在同一水平，这为工业应用提供了很大的可能性。
• Synthesis of new chiral fluorescent sensors and their applications in enantioselective discrimination
  作者：Xueyan Zhang、Shengxin Chen、Pei Xu、Qiuhan Yu、Zhenya Dai

  DOI：10.1016/j.tetlet.2017.06.025

  日期：2017.7

  Five novel sensors (R,R)-3–6 and (S, S)-6 were synthesized and developed for enantioselective recognition of chiral compounds. Sensor 6 with two thiourea groups and steric π-conjugation frameworks could discriminate different chiral substrates, including acidic compounds, basic compounds, and neutral compounds. These results disclosed that the outstanding performance of enantioselective discrimination

  合成并开发了五个新颖的传感器（R，R）-3-6和（S，S）-6用于手性化合物的对映选择性识别。具有两个硫脲基和空间π共轭框架的传感器6可以区分不同的手性底物，包括酸性化合物，碱性化合物和中性化合物。这些结果表明，对映选择性鉴别的杰出表现可以归因于硫脲基团，其作为氢键供体，并且提供了合适的手性环境的主体的庞大空间部分。该结果在手性传感器的设计和手性产品的高通量分析中将具有很大的实用价值。
• Discrimination of enantiomers of α-amino acids by chiral derivatizing reagents fromtrans-1,2-diaminocyclohexane
  作者：Magdalena Kaik、Jadwiga Gajewy、Jakub Grajewski、Jacek Gawronski

  DOI：10.1002/chir.20435

  日期：2008.3

  New chiral derivatizing reagents (CDAs) derived from trans-1,2-diaminocyclohexane, having an electron-deficient aromatic substituent (either an aromatic imide or 3,5-dinitrobenzamide) and rigid structure (either an amide or a urea linker), are reported. Significant shift differences of diastereotopic protons in the 1H NMR signals are observed for enantiomers of suitably protected alpha-amino acids, linked

  由反式1,2-二氨基环己烷衍生而来的新型手性衍生试剂（CDA），具有电子不足的芳族取代基（芳族酰亚胺或3,5-二硝基苯甲酰胺）和刚性结构（酰胺或脲连接基）报告。对于通过共价键连接到CDA的，具有适当保护的α-氨基酸的对映异构体，在1H NMR信号中观察到非对映质子的显着位移差异。提出了一个简单的通用模型，对观察到的对映异构体进行了合理化处理，并基于半经验构象搜索。
• A photo-stable fluorescent chiral thiourea probe for enantioselective discrimination of chiral guests
  作者：Xueyan Zhang、Qiuhan Yu、Shengxin Chen、Zhenya Dai

  DOI：10.1039/c8nj00374b

  日期：——

  enhanced the enantioselectivity of chiral guests. In addition, for amino acids, the sensor 4 showed high enantioselectivity, and precipitates visible by the naked eye appeared; however, for chiral amines, the enantioselectivity decreased. This was attributed to weaker hydrogen bond interaction between the amino groups of chiral amines and the sensor. Both the thiourea and acidic hydroxyl groups are

  本文中，衍生自（1 R，2 R）-1,2-环己二胺和四苯基乙烯（TPE）的手性硫脲席夫碱被用作高效手性传感器，用于通过离子对和氢对各种酸和胺进行对映选择性鉴别键相互作用。相较于传感器的情况下5和6，传感器的额外硫脲和氢基团4至关重要，并大大提高了手性客人的对映选择性。此外，对于氨基酸，传感器4表现出高的对映选择性，并出现肉眼可见的沉淀。但是，对于手性胺，对映选择性降低。这归因于手性胺的氨基和传感器之间的氢键相互作用较弱。硫脲和酸性羟基对于手性TPE硫脲都是必不可少的，从而为手性底物的高效对映选择性鉴别提供了合适的手性环境。我们的发现对新型手性传感器的设计将具有重要的价值。
• Novel NMR chiral solvating agents derived from (1R,2R)-diaminocyclohexane: synthesis and enantiodiscrimination for chiral carboxylic acids
  作者：Xuemei Yang、Guitao Wang、Cheng Zhong、Xiaojun Wu、Enqin Fu

  DOI：10.1016/j.tetasy.2006.03.011

  日期：2006.3

  A series of new compounds, (1R,2R)-1-(1',8-naphthalimide)-2-aminocyclohexane 1 and its 4'-derivatives 2 and 3 derived from (1R,2R)-1,2-diaminocyclohexane have been synthesized conveniently and efficiently. H-1 NMR spectroscopy was employed to investigate their enantiodiscriminating ability. Compared with alpha-phenylethylamine, a commercially available chiral solvating agent (CSA), these compounds exhibited better enantiodiscriminating ability toward the chiral carboxylic acids we had chosen, distinguishing them as promising and practical CSAs. (c) 2006 Elsevier Ltd. All rights reserved.