N-[(1R,2R)-2-aminocyclohexane]-2-hydroxybenzamide

• 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: N-[(1R,2R)-2-aminocyclohexane]-2-hydroxybenzamide
• 英文别名: (1R,2R)-trans-1-amino-2-(2-hydroxybenzamide)cyclohexane；N-[(1S,2S)-2-aminocyclohexyl]-2-hydroxybenzamide
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: DAOKYNYDFYHWMY-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cobalt(II) chloride hexahydrate 、 potassium tert-butylate 、 N-[(1R,2R)-2-aminocyclohexane]-2-hydroxybenzamide 生成 K[Co(RR-trans-1-amino-2-(2-hydroxybenzamide)cyclohexane-2H)2]
  参考文献：
  名称：

  Hydrogen-bonding interactions, geometrical selectivity and spectroscopic properties of cobalt(III) complexes with unsymmetrical tridentate amine-amidato-phenolato type ligands

  摘要：

  Four cobalt(III) complexes with the formula of [Co(Ln)(2)] bearing tridentate amine-amidato-phenolato-type ligands (Ln: n = 1-4) were synthesized. All of the complexes were characterized by H-1 NMR spectroscopy and X-ray analysis. The geometrical selectivity was found to depend on the flexibility of the amine-amidato chelate in combination with the planar 2-oxybenzamido 6-membered chelate; that is, the amine-amidato 5-membered chelate took the mer-type geometry, and the 6-membered chelate took the fac-type geometry. In most of the mer-type complexes, intermolecular double hydrogen bonds via amidato(O) and amino group were selectively formed between their enantiomeric pairs of mononuclear complexes. In the case of two chiral ligands {L2(2) = 2-amino-1-(2-oxybenzamido) propane; L3(2) = trans-1-amino-2-(2-oxybenzamido)cyclohexane}, [Co(L3)(2)] showed diastereoselectivity while [Co(L2)(2)] did not. Furthermore, PPh4[Co(L1)(2)] (L1(2) = 2-amino-1-(2-oxybenzamido)-2-methylpropane) showed an apparent solvatochromic behavior in several solvents. Although the molecular structures of [Co(L2 or L3)(2)] are quite similar to that of [Co(L1)(2)] , these complexes did not exhibit such a solvatochromic behavior. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.01.011
• 作为产物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 水杨酸苯酯 以 异丙醇 为溶剂， 生成 N-[(1R,2R)-2-aminocyclohexane]-2-hydroxybenzamide
  参考文献：
  名称：

  反式环己烷-1,2-二胺手性单水杨酰胺有机催化α,α-二取代醛与硝基烯烃的不对称共轭加成反应

  摘要：

  衍生自手性反式-环己烷-1,2-二胺的伯胺-水杨酰胺用作有机催化剂，用于将 α,α-二取代醛对映选择性共轭加成到芳基化和杂芳基化硝基烯烃。该反应在作为添加剂的4-二甲氨基吡啶存在下在作为溶剂的二氯甲烷中在室温下进行。以高达 95% 的对映选择性获得相应的对映体富集的 γ-硝基醛。理论计算用于证明立体感应的原因。

  DOI：

  10.3390/molecules23010141
• 作为试剂：
  描述：

  1-氟-3-(2-硝基乙烯基)苯 、 异丁醛 在 4-二甲氨基吡啶 、 N-[(1R,2R)-2-aminocyclohexane]-2-hydroxybenzamide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以62%的产率得到(S)-3-(4-fluorophenyl)-2,2-dimethyl-4-nitrobutanal
  参考文献：
  名称：

  反式环己烷-1,2-二胺手性单水杨酰胺有机催化α,α-二取代醛与硝基烯烃的不对称共轭加成反应

  摘要：

  衍生自手性反式-环己烷-1,2-二胺的伯胺-水杨酰胺用作有机催化剂，用于将 α,α-二取代醛对映选择性共轭加成到芳基化和杂芳基化硝基烯烃。该反应在作为添加剂的4-二甲氨基吡啶存在下在作为溶剂的二氯甲烷中在室温下进行。以高达 95% 的对映选择性获得相应的对映体富集的 γ-硝基醛。理论计算用于证明立体感应的原因。

  DOI：

  10.3390/molecules23010141

文献信息

• Greatly Enhanced Fluorescence by Increasing the Structural Rigidity of an Imine: Enantioselective Recognition of 1,2-Cyclohexanediamine by a Chiral Aldehyde
  作者：Yimang Xu、Shanshan Yu、Qi Chen、Xuemin Chen、Meng Xiao、Liming Chen、Xiaoqi Yu、Yong Xu、Lin Pu

  DOI：10.1002/chem.201504686

  日期：2016.4.18

  sensitive fluorescence enhancement sensor through incorporation of an additional hydrogen bonding unit to increase the structural rigidity of the reaction product of the aldehyde with the diamine. This new chiral aldehyde is synthesized in one step from the reaction of (S)‐3‐formylBINOL with salicyl chloride. When treated with trans‐1,2‐cyclohexanediamine in ethanol, it shows greatly enhanced fluorescence

  对手性二胺不具有荧光响应性的醛已通过加入额外的氢键合单元，以提高醛与二胺的反应产物的结构刚性而转变为灵敏的荧光增强传感器。这种新的手性醛是从（S）-3-甲酰基BINOL与水杨酰氯的反应一步合成的。当在乙醇中用反式1,2-环己二胺处理时，它在λ处显示出大大增强的荧光＝ 410nm，具有良好的对映选择性。NMR和质谱法用于研究手性醛与二胺的反应。这项研究揭示了一个两阶段的反应机理，包括快速的亚胺形成和缓慢的酯裂解。
• Manganese amido-imine bisphenol Hangman complexes
  作者：Jenny Y. Yang、Daniel G. Nocera

  DOI：10.1016/j.tetlet.2008.05.111

  日期：2008.8

  A modular ligand macrocycle is composed from two phenolic groups linked to a cyclohexane bridge through an amide bond and an imine bond. The stability of the asymmetric linkers to metathesis permits a macrocyclic platform to be assembled from the condensation of two different phenolic groups in a single-step, high yield, reaction. The primary coordination sphere may be tuned with functional groups on one phenolic group. The other phenolic group may be modified with a scaffold possessing a proton transfer group. In this way, control over the secondary coordination sphere of the macrocycle is achieved. Manganese complexes of the amido-imine linked macrocycle catalytically epoxidizes 1,2-dihydronapthalene using sodium hypochlorite as the oxidant. The amido-imine macrocycles represent a new metal active site capable of supporting high oxidation states and attendant atom transfer chemistry while at the same time permitting control over the primary and secondary sphere of the metal center. (C) 2008 Elsevier Ltd. All rights reserved.