(1-氮杂双环[2.2.2]-3-辛基)-(4-甲氧基苄基)-胺 | 17186-53-7

• 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
• 中文名称: (1-氮杂双环[2.2.2]-3-辛基)-(4-甲氧基苄基)-胺
• 中文别名: N-环己基-L-苯丙氨酰胺
• 英文名称: L-phenylalanine cyclohexylamide
• 英文别名: (S)-2-amino-N-cyclohexyl-3-phenylpropanamide；(S)-phenylalanine cyclohexylamide；L-Phenylalanine-cyclohexylamide；(2S)-2-amino-N-cyclohexyl-3-phenylpropanamide
• CAS: 17186-53-7
• 化学式: C₁₅H₂₂N₂O
• mdl: MFCD00672357
• 分子量: 246.352
• InChiKey: ZMBVNXGMRQPTHV-AWEZNQCLSA-N

物化性质

• 熔点：
  96-99 °C
• 溶解度：
  溶于二氯甲烷、DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (1-氮杂双环[2.2.2]-3-辛基)-(4-甲氧基苄基)-胺 在 对甲苯磺酸 、 sodium sulfate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (2R,5S)-1-Benzotriazol-2-ylmethyl-5-benzyl-3-cyclohexyl-2-phenyl-imidazolidin-4-one
  参考文献：
  名称：

  Novel Syntheses of Enantiopure Hexahydroimidazo[1,5-b]isoquinolines and Tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones via Iminium Cation Cyclizations

  摘要：

  Condensations of chiral diamines 11a-c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a-c; similar condensations of alpha-amino-amides 10a-c with benzotriazole and paraformaldehyde gave 14a-c. Subsequent treatment of 12a-c and 14a-c with AlCl3 led to enantiopure tricyclic 1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolines 1a-c and 2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones 15a-c, respectively, via Lewis acid promoted iminium cation cyclizations.

  DOI：

  10.1021/jo0203241
• 作为产物：
  描述：

  ethoxycarbonyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate 在 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 (1-氮杂双环[2.2.2]-3-辛基)-(4-甲氧基苄基)-胺
  参考文献：
  名称：

  Practical resolution of an atropoisomeric α,α-disubstituted glycine with l-phenylalanine cyclohexylamide as chiral auxiliary

  摘要：

  L-Phenylalanine cyclohexylamide has been used as a chiral auxiliary for the medium-scale resolution of 2',1':1,2;1 ",2 ":3,4-dinaphthcyciohepta- 1,3-diene-6-amino-6-carboxylic acid (Bin), an alpha,alpha-disubstituted glycine with only axial dissymmetry. Coupling of X-Bin-OH (X=Ac; Bz) with H-(L)-Phe-NH-C6H11 by the EDC/HOBt method gave the dipeptide diastereoisomers X-(R)-Bin-(L)-Phe-NH-C6H11 and X-(S)-Bin-(L)-Phe-NH-C6H11, which were separated by crystallization (X=Bz) and/or chromatography. Extensive acidic hydrolysis, followed by esterification of the resulting free amino acid enantiomers, led to enantiomerically pure (-)-(R)-H-Bin-OMe and (+)-(S)-H-Bin-OMe with high yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00253-5

文献信息

• An Efficient Strategy to Orthogonally Protected (<i>R</i>)- and (<i>S</i>)-α-Methyl(alkyl)serine-Containing Peptides via a Novel Azlactone/Oxazoline Interconversion Reaction
  作者：Daniel Obrecht、Michael Altorfer、Christian Lehmann、Peter Schönholzer、Klaus Müller

  DOI：10.1021/jo952068g

  日期：1996.1.1

  for the synthesis of (R)- and (S)-alpha-methyl(alkyl)serine-containing peptides is presented. Using (S)-phenylalanine cyclohexylamide 6 as chiral auxiliary, the optically pure azlactones (R)- and (S)-2 were synthesized via a novel azlactone/oxazoline interconversion reaction (Figures 3 and 6). These azlactones constitute fully protected and activated synthetic equivalents of (R)- and (S)-alpha-methylserine

  提出了一种合成（R）-和（S）-α-甲基（烷基）丝氨酸的肽的新策略。使用（S）-苯丙氨酸环己酰胺6作为手性助剂，通过新颖的氮杂内酯/恶唑啉互变反应合成了光学纯的氮杂内酯（R）-和（S）-2（图3和6）。这些a内酯构成（R）-和（S）-α-甲基丝氨酸的完全保护和活化的合成等同物，可以直接掺入肽中，而无需进一步的保护基操纵。像其他的α，α-二烷基甘氨酸一样，光学纯的α-烷基丝氨酸可用于稳定短肽中的β转角和α螺旋构象。
• Synthesis and conformational studies of peptido-squaramide foldable modules: a new class of turn-mimetic compounds
  作者：Luis Martínez、Angel Sampedro、Elena Sanna、Antoni Costa、Carmen Rotger

  DOI：10.1039/c2ob06715c

  日期：——

  The β-turn unit is one of the most important secondary structure elements in proteins. The access to new conformationally controlled foldable modules can afford compounds with interesting bioactivities. Here, we describe a new family of peptido-squaramide foldable modules based on the considerable potential of the squaramide unit as a hydrogen bond donor and acceptor as well as the low rotational barrier of the C–N bond. The conformational analysis by NMR of these modules in chloroform and acetonitrile solution shows that a disecondary squaramide with the 4-aminobutyric acid in one of its substituents can mimic the β-turn structure driven by the formation of an intramolecular hydrogen bonded ten-membered ring. This structure, although flexible, has been successfully combined with dipeptide chains to induce the formation of a hairpin-like structure driven by the formation of several cross-strand intramolecular hydrogen bonds.

  β-转角单元是蛋白质中最重要的一种二级结构元素。具有新型构象控制的折叠模块可赋予化合物有趣的生物活性。在此，我们描述了一系列基于方形酰胺单元作为氢键供体和受体的巨大潜力以及碳氮键的低旋转能垒的肽基方形酰胺折叠模块。通过核磁共振对这些模块在氯仿和丙酮腈溶液中的构象分析表明，一种含有4-氨基丁酸作为其取代基之一的双二级方形酰胺可模拟由形成一个分子内氢键的十元环驱动的β-转角结构。尽管该结构具有柔性，但它已成功地与二肽链结合，通过形成多个跨越链的分子内氢键驱动了形成类似发夹的结构。
• Chiral Primary−Tertiary Diamine Catalysts Derived From Natural Amino Acids for <i>syn</i>-Aldol Reactions of Hydroxy Ketones
  作者：Jiuyuan Li、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1021/jo802557p

  日期：2009.2.20

  A series of primary-tertiary diamine catalysts were designed and synthesized from primary natural amino acids. Application of these new chiral catalysts in direct aldol reactions of α-hydroxyketones showed very good catalytic activity (up to 97% yield) and high syn selectivity (up to syn/ anti = 30:1, 99% ee).

  从伯天然氨基酸设计合成了一系列伯叔二胺催化剂。这些新的手性催化剂在α-羟基酮的直接醛醇缩合反应中的应用显示出非常好的催化活性（高达97％的收率）和高的合成选择性（高达syn / anti = 30：1，99％ee）。
• Access to Spirocyclic Benzothiophenones with Multiple Stereocenters via an Organocatalytic Cascade Reaction
  作者：Bedřich Formánek、Jiří Tauchman、Ivana Císařová、Jan Veselý

  DOI：10.1021/acs.joc.0c00882

  日期：2020.7.2

  derivatives containing three stereocenters were prepared via one-step synthesis in yields ranging from 88 to 96% and in enantioselectivities (enantiomeric excess (ee)) ranging from 85 to 97%, with diastereoselectivities of approximately 14/2/1. Therefore, this method provides an efficient route for the synthesis of a new class of optically active 2-spirobenzothiophenones.

  本报告描述了在金鸡纳生物碱胺存在下2-亚烷基苯并[ b ]噻吩酮衍生物与烯酮之间的有机催化级联反应。通过一步合成，制备了包含三个立体中心的螺苯并噻吩苯甲酸环己烷衍生物，其产率为88％至96％，对映选择性（对映体过量（ee））为85至97％，非对映选择性约为14/2/1。因此，该方法为合成新型的光学活性的2-螺苯并噻吩酮提供了有效的途径。
• <scp>L</scp>-Phenylalanine Cyclohexylamide: A simple and convenient auxiliary for the synthesis of optically pure α,α-disubstituted (<i>R</i>)- and (<i>S</i>)-amino acids
  作者：Daniel Obrecht、Udo Bohdal、Clemens Broger、Daniel Bur、Christian Lehmann、Ruth Ruffieux、Peter Schönholzer、Clive Spiegler、Klaus Müller

  DOI：10.1002/hlca.19950780305

  日期：1995.5.10

  synthesis of a series of optically pure α,α-disubstituted (R)- and (S)-amino acids of type 1, such as (R)- and (S)-2-methyl-phenylalanine (1a), (R)- and (S)-2-methyl-2-phenylglycine (1b), and (R)- and (S)-2-methylvaline (1c; Scheme 3). These amino acids were efficiently transformed into the suitably protected and activated amino acid building blocks (R)- and (S)-12b and (R)- and (S)-12c (Scheme 4) which are

  这项工作描述了L-苯丙氨酸环己基酰胺（5C），其为简单的，价格便宜，且功能强大的手性助剂为一系列光学纯α，α-二取代的（的合成- [R ）-和（小号）型的α-氨基酸1，这样如（R）-和（S）-2-甲基-苯丙氨酸（1a），（R）-和（S）-2-甲基-2-苯甘氨酸（1b）以及（R）-和（S）-2 -甲基缬氨酸（1c；方案3）。这些氨基酸被有效地转化为适当保护和活化的氨基酸构件（R）和（S）-12b以及（R）-和（S）-12c（方案4），它们已经准备好通过溶液或固相技术掺入肽中。基于属于非对映异构体肽系列6和7的6b，6c和7a的晶体结构，确定该系列的每个成员的绝对构型。对于6b和7a分别观察到II'和I型的β-转角几何形状，而6c以扩展构象结晶。讨论了侧链变化对这些三酰胺的构象和晶体堆积的影响。