(1R,2R)-2-aminocyclohexanecarboxylic acid hydrochloride | 158414-46-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2R)-2-aminocyclohexanecarboxylic acid hydrochloride
• 英文别名: (R,R)-trans-2-aminocyclohexanecarboxylic acid hydrochloride；(1R,2R)-2-aminocyclohexylcarboxylic acid hydrochloride；(1R,2R)-2-aminocyclohexane-1-carboxylic acid;hydrochloride
• CAS: 158414-46-1
• 化学式: C₇H₁₃NO₂*ClH
• 分子量: 179.647
• InChiKey: QNIOBHOEZYKCJV-KGZKBUQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.12
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-aminocyclohexanecarboxylic acid hydrochloride 在 1,4-diazabicycloundecene 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 11.0h， 生成 Boc-(R,R)-trans-2-aminocyclohexanecarboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis and Characterization of trans-2-Aminocyclohexanecarboxylic Acid Oligomers:  An Unnatural Helical Secondary Structure and Implications for β-Peptide Tertiary Structure

  摘要：

  The preperation, crystal structures, and circular dichroism(CD)spectra of two oligomers of optically active trans-2-aminocyclohexanecarboxylic acid are reported. In the solid state, both the tetramer and the hexamer of this beta-amino acid display a helical conformation that involves 14-membered-ring hydrogen bonds between a carbonyl oxygen and the amide proton of the second residue toward the N-terminus. (For comparison, the familiar cc-helix observed in conventional peptides is associated with a 13-membered-ring hydrogen, bond between a carbonyl oxygen and the amide proton of the fourth residue toward the C-terminus.) These. :crystallographic data, along with CD data obtained in methanol, suggest that the 14-helix constitutes a stable secondary structure for beta-amino acid oligomers ("beta-peptides"). In addition, the cryst al packing pattern observed for the hexamer offers a blueprint for the design of beta-peptides that might adopt a helical bundle tertiary structure.

  DOI：

  10.1021/ja990748l
• 作为产物：
  描述：

  (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid 在 乙酰氯 、 氨 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 以74%的产率得到(1R,2R)-2-aminocyclohexanecarboxylic acid hydrochloride
  参考文献：
  名称：

  对映体纯 β-氨基酸：方便获得反式-2-氨基环己烷甲酸的两种对映体

  摘要：

  对映体纯的反式-2-氨基环己烷甲酸是螺旋β-肽的重要组成部分。我们在这里报告说，这种氨基酸可以通过简单的一锅法从反式环己烷-1,2-二羧酸以良好的收率获得，包括环化成酸酐，用氨形成酰胺，以及随后的霍夫曼型降解苯碘（III）双（三氟乙酸盐）（PIFA）作为氧化剂。通过分别用 Fmoc-OSu 和 BOC2O 处理氨基酸获得 N-Fmoc-和 N-BOC-保护的衍生物。N-BOC 衍生物可以通过直接从反式-环己烷-1,2-二羧酸到 N-BOC 保护的氨基酸的一锅法制备，以更高的总产率制备。起始反式 1 的两种对映异构体，通过使用（R）-或（S）-1-苯乙胺分离市售的外消旋反式-1,2-环己烷二甲酸，可以容易地大量获得2-环己烷二甲酸。从 (R)-1-苯乙胺获得的非对映异构纯盐的 X 射线晶体学显示，二酸组分的构型是 (1R,2R)，而不是文献中报道的 (1S,2S)。(© Wiley-VCH Verlag

  DOI：

  10.1002/1099-0690(200209)2002:17<2948::aid-ejoc2948>3.0.co;2-e

文献信息

• Asymmetric synthesis of (–)-(1R,2S)-cispentacin and related cis- and trans-2-amino cyclopentane- and cyclohexane-1-carboxylic acids
  作者：Stephen G. Davies、Osamu Ichihara、Isabelle Lenoir、Iain A. S. Walters

  DOI：10.1039/p19940001411

  日期：——

  The antifungal antibiotic (–)-(1R,2S)-2-aminocyclopentane-1-carboxylic acid (cispentacin)8 and its cyclohexane homologue 14 have been prepared utilizing the highly stereoselective conjugate addition of homochiral lithium N-benzyl-N-α-methylbenzylamide 5. The corresponding trans-β-amino acids 10 and 16 were also prepared via the selective epimerization of the cis-β-amino ester conjugate addition products

  抗真菌抗生素（–）-（1 R，2 S）-2-氨基环戊烷-1-羧酸（顺喷塔星）8及其环己烷同系物14是通过高立体选择性共轭加成手性锂N-苄基-N-制备的。 α-甲基苄基酰胺5。还通过顺式-β-氨基酯缀合物加成产物的选择性差向异构化制备了相应的反式-β-氨基酸10和16。
• Parallel assembly of dipolar columns composed of a stacked cyclic tri-β-peptide
  作者：Futoshi Fujimura、Makoto Fukuda、Junji Sugiyama、Tomoyuki Morita、Shunsaku Kimura

  DOI：10.1039/b600407e

  日期：——

  A novel cyclic trimer of a β-amino acid, trans-2-aminocyclohexylcarboxylic acid, was synthesized and its conformation and ability to form assemblies investigated. FT-IR and NMR measurements and computational calculations showed that this cyclic tri-β-peptide has a C3-symmetric conformation with trans amide groups. A notable feature of the conformation is a vertical and parallel orientation of the three amide groups to the cyclic skeleton. The cyclic tri-β-peptide was crystallized from a solution in trifluoroacetic acid–methanol (or trifluoroacetic acid–water) to yield a rod-shaped molecular assembly, as observed by TEM. The electron crystallography of the rod-shaped assembly both in suspension and in ultrathin cross-section revealed that the cyclic tri-β-peptides were stacked up to form molecular columns, and that a two-fold screw symmetry operation along the column direction was present in the unit cell, which contained two cyclic tri-β-peptides. This indicates that all the amide groups are oriented in the same direction. Since any two molecular columns are staggered by a quarter of a c-axis length and aligned parallel to each other, the dipole moments of the columns are aligned to enhance the strength additively in the whole assembly.

  我们合成了一种δ-氨基酸的新型环状三聚体--反式-2-氨基环己基羧酸，并研究了它的构象和形成集合体的能力。傅立叶变换红外光谱和核磁共振测量以及计算表明，这种环状三δ肽具有反式酰胺基团的 C3 对称构象。该构象的一个显著特点是三个酰胺基团与环状骨架的垂直和平行取向。环状三δ肽在三氟乙酸-甲醇（或三氟乙酸-水）溶液中结晶后，经 TEM 观察，生成了棒状分子组装体。对棒状组装体的悬浮液和超薄横截面进行电子晶体学分析后发现，环状三牺²肽堆叠在一起形成分子柱，在包含两个环状三牺²肽的单元胞中，沿分子柱方向存在两重螺旋对称操作。这表明所有的酰胺基团都朝向同一方向。由于任何两个分子柱都错开了四分之一的 c 轴长度并相互平行排列，因此分子柱的偶极矩排列在一起，从而增强了整个组装体的叠加强度。
• Enantiomerically Pure β-Amino Acids: A Convenient Access to Both Enantiomers of trans-2-Aminocyclohexanecarboxylic Acid
  作者：Albrecht Berkessel、Katja Glaubitz、Johann Lex

  DOI：10.1002/1099-0690(200209)2002:17<2948::aid-ejoc2948>3.0.co;2-e

  日期：2002.9

  Enantiomerically pure trans-2-aminocyclohexanecarboxylic acid is an important building block for helical β-peptides. We report here that this amino acid can be obtained from trans-cyclohexane-1,2-dicarboxylic acid in good yield by a simple one-pot procedure comprising cyclization to the anhydride, amide formation with ammonia, and a subsequent Hofmann-type degradation with phenyliodine(III) bis(trifluoroacetate)

  对映体纯的反式-2-氨基环己烷甲酸是螺旋β-肽的重要组成部分。我们在这里报告说，这种氨基酸可以通过简单的一锅法从反式环己烷-1,2-二羧酸以良好的收率获得，包括环化成酸酐，用氨形成酰胺，以及随后的霍夫曼型降解苯碘（III）双（三氟乙酸盐）（PIFA）作为氧化剂。通过分别用 Fmoc-OSu 和 BOC2O 处理氨基酸获得 N-Fmoc-和 N-BOC-保护的衍生物。N-BOC 衍生物可以通过直接从反式-环己烷-1,2-二羧酸到 N-BOC 保护的氨基酸的一锅法制备，以更高的总产率制备。起始反式 1 的两种对映异构体，通过使用（R）-或（S）-1-苯乙胺分离市售的外消旋反式-1,2-环己烷二甲酸，可以容易地大量获得2-环己烷二甲酸。从 (R)-1-苯乙胺获得的非对映异构纯盐的 X 射线晶体学显示，二酸组分的构型是 (1R,2R)，而不是文献中报道的 (1S,2S)。(© Wiley-VCH Verlag
• Synthesis and Characterization of <i>trans</i>-2-Aminocyclohexanecarboxylic Acid Oligomers:  An Unnatural Helical Secondary Structure and Implications for β-Peptide Tertiary Structure
  作者：Daniel H. Appella、Laurie A. Christianson、Isabella L. Karle、Douglas R. Powell、Samuel H. Gellman

  DOI：10.1021/ja990748l

  日期：1999.7.1

  The preperation, crystal structures, and circular dichroism(CD)spectra of two oligomers of optically active trans-2-aminocyclohexanecarboxylic acid are reported. In the solid state, both the tetramer and the hexamer of this beta-amino acid display a helical conformation that involves 14-membered-ring hydrogen bonds between a carbonyl oxygen and the amide proton of the second residue toward the N-terminus. (For comparison, the familiar cc-helix observed in conventional peptides is associated with a 13-membered-ring hydrogen, bond between a carbonyl oxygen and the amide proton of the fourth residue toward the C-terminus.) These. :crystallographic data, along with CD data obtained in methanol, suggest that the 14-helix constitutes a stable secondary structure for beta-amino acid oligomers ("beta-peptides"). In addition, the cryst al packing pattern observed for the hexamer offers a blueprint for the design of beta-peptides that might adopt a helical bundle tertiary structure.