N-[(1R,2R)-2-aminocyclohexyl]-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-aminocyclohexyl]-2-hydroxybenzamide
• 化学式: C₁₃H₁₈N₂O₂
• 分子量: 234.298
• InChiKey: DAOKYNYDFYHWMY-GHMZBOCLSA-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：
  0.461
• 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：

  甲醇 、 cobalt(II) chloride hexahydrate 、 potassium tert-butylate 、 N-[(1R,2R)-2-aminocyclohexyl]-2-hydroxybenzamide 反应 2.0h， 以32%的产率得到K[Co(trans-1-amino-2-(2-hydroxybenzamide)cyclohexane-2H)₂]·3CH₃OH
  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：

  水杨酰氯 在 三乙胺 作用下， 以 氘代氯仿 、 二氯甲烷 、 氘代甲醇 为溶剂， 反应 0.17h， 生成 N-[(1R,2R)-2-aminocyclohexyl]-2-hydroxybenzamide
  参考文献：
  名称：

  通过增加亚胺的结构刚性大大增强了荧光：手性醛对1,2-环己二胺的对映选择性识别

  摘要：

  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。

  DOI：

  10.1002/chem.201504686
• 作为试剂：
  描述：

  N-苯基马来酰亚胺 、 异丁醛 在 N-[(1R,2R)-2-aminocyclohexyl]-2-hydroxybenzamide 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以98%的产率得到(R)-2-(2,5-dioxo-1-phenylpyrrolidin-3-yl)-2-methylpropanal
  参考文献：
  名称：

  手性伯胺-水杨酰胺有机催化醛对马来酰亚胺的对映选择性迈克尔加成

  摘要：

  衍生自手性反式-环己烷-1,2-二胺的伯胺-水杨酰胺用作醛的对映选择性共轭加成的有机催化剂，主要是 α,α-二取代到 N-取代的马来酰亚胺。反应在室温下在甲苯作为溶剂中进行。以高产率和高达 94% 的对映选择性获得了相应的对映体富集的加合物。理论计算用于证明立体感应的合理性。

  DOI：

  10.3390/molecules23123299

文献信息

• Geometric Selectivity, Hydrogen-Bonding Interaction, and Solvatochromism of Bis{<i>N</i>-(aminoalkyl)salicylamidato(2−)}cobaltate(III)
  作者：Ryoji Mitsuhashi、Takayoshi Suzuki、Yukinari Sunatsuki、Masaaki Kojima

  DOI：10.1246/cl.2011.696

  日期：2011.7.5

  Cobalt(III) complexes with N-(aminoalkyl)salicylamide dianions, Ln2− (n = 1–4), have been prepared and their molecular and crystal structures have been determined. The geometric (mer- or fac-) selectivity of [Co(Ln)2]− complexes was dependent on the number of the amine–amidato chelate ring member. Intermolecular homochiral hydrogen-bonds and solvatochromic behavior of the complexes were also observed.

  我们制备了具有 N-（氨基烷基）水杨酰胺二元离子 Ln2- （n = 1-4）的钴（III）配合物，并确定了它们的分子和晶体结构。Co(Ln)2]-配合物的几何选择性（mer-或facet-）取决于胺酰胺螯合环成员的数量。此外，还观察到了络合物分子间的同手性氢键和溶解变色行为。
• Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
  作者：Alejandro Torregrosa-Chinillach、Adrien Moragues、Haritz Pérez-Furundarena、Rafael Chinchilla、Enrique Gómez-Bengoa、Gabriela Guillena

  DOI：10.3390/molecules23123299

  日期：——

  amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to N-substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The corresponding enantioenriched adducts were obtained with high yields and enantioselectivities up to 94%. Theoretical calculations

  衍生自手性反式-环己烷-1,2-二胺的伯胺-水杨酰胺用作醛的对映选择性共轭加成的有机催化剂，主要是 α,α-二取代到 N-取代的马来酰亚胺。反应在室温下在甲苯作为溶剂中进行。以高产率和高达 94% 的对映选择性获得了相应的对映体富集的加合物。理论计算用于证明立体感应的合理性。
• Hydrogen-bonding interactions, geometrical selectivity and spectroscopic properties of cobalt(III) complexes with unsymmetrical tridentate amine-amidato-phenolato type ligands
  作者：Ryoji Mitsuhashi、Takayoshi Suzuki、Yukinari Sunatsuki、Masaaki Kojima

  DOI：10.1016/j.ica.2013.01.011

  日期：2013.4

  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.
• 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。