5-[tert-butoxycarbonyl-(3,5-di-tert-butylbenzyl)-amino]pentanoic acid | 518033-67-5

• 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: 5-[tert-butoxycarbonyl-(3,5-di-tert-butylbenzyl)-amino]pentanoic acid
• 英文别名: 5-[(3,5-Ditert-butylphenyl)methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoic acid
• CAS: 518033-67-5
• 化学式: C₂₅H₄₁NO₄
• 分子量: 419.605
• InChiKey: JVDHPAYHAVEMJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[tert-butoxycarbonyl-(3,5-di-tert-butylbenzyl)-amino]pentanoic acid 在 lithium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 3.33h， 生成 2-[5-(3,5-di-tert-butylbenzylamino)pentanoylamino]-3-phenylpropanoic acid hydrochloride
  参考文献：
  名称：

  Structure−Function Relationship of Amino Acid−[2]Rotaxanes

  摘要：

  Synthetic methodology was developed to construct amino acid-[2]rotaxanes that have phenylalanine and 3,5-di-tert-butylbenzene as blocking groups and dibenzo-24-crown-8, derivatized with either N-acetylargininyl or a carboxylic group, as the ring. A relative measure of the intramolecular interaction energies between the functional groups in DMSO/water mixtures is obtained by comparing their pK(a) values. Rotaxane structures were investigated through 2D NMR analysis and molecular dynamics simulations. Association constants for complexes of amino acids and rotaxanes in various protonation states were determined in a variety of solvent systems by H-1 NMR analysis. The unique intracomponent interactions that exist in the rotaxanes and their ability to act as artificial receptors are discussed.

  DOI：

  10.1021/jo026530q
• 作为产物：
  描述：

  N-(di-3,5-tert-butylbenzyl)-δ-valerolactam 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 5-[tert-butoxycarbonyl-(3,5-di-tert-butylbenzyl)-amino]pentanoic acid
  参考文献：
  名称：

  Structure−Function Relationship of Amino Acid−[2]Rotaxanes

  摘要：

  Synthetic methodology was developed to construct amino acid-[2]rotaxanes that have phenylalanine and 3,5-di-tert-butylbenzene as blocking groups and dibenzo-24-crown-8, derivatized with either N-acetylargininyl or a carboxylic group, as the ring. A relative measure of the intramolecular interaction energies between the functional groups in DMSO/water mixtures is obtained by comparing their pK(a) values. Rotaxane structures were investigated through 2D NMR analysis and molecular dynamics simulations. Association constants for complexes of amino acids and rotaxanes in various protonation states were determined in a variety of solvent systems by H-1 NMR analysis. The unique intracomponent interactions that exist in the rotaxanes and their ability to act as artificial receptors are discussed.

  DOI：

  10.1021/jo026530q

文献信息

• Synthesis and Investigation of Host-[2]Rotaxanes That Bind Metal Cations
  作者：Xiaoyang Wang、Jing Zhu、David B. Smithrud

  DOI：10.1021/jo100330e

  日期：2010.5.21

  Materials that bind metal cations are highly sought after for new devices. In this report, we show that rotaxanes can transfer metal cations with picrate, perchlorate, or chloride counterions from an aqueous solution into chloroform. The rotaxanes contain a dibenzyl-24-crown-8 ether as the wheel with either a benzyl-18-crown-6 ether (CEBG-R1−3) or a 3,5-dimethylbenzyl moiety (ArBG-R) as one blocking

  结合金属阳离子的材料在新设备中非常受追捧。在此报告中，我们表明轮烷能够将金属阳离子与苦味酸根，高氯酸根或氯离子抗衡离子从水溶液转移到氯仿中。轮烷含有二苄基-24-冠-8醚作为轮子，苄基-18-冠-6醚（CEBG-R1-3）或3,5-二甲基苄基部分（ArBG-R）作为一个保护基。从水溶液中以毫摩尔范围有效地萃取了碱金属盐和碱性苦味酸盐到氯仿中。对于氯仿中的配合物，特别是对于二价阳离子Mg 2+，得出了较大的缔合常数。。将抗衡离子转换为氯离子会大大减少提取的盐量。为了探讨轮烷的转移机理，比较了用CEBG-R1，ArBG-R，苄基-18-冠-6醚（B18C6）萃取的NaClO 4，KClO 4，NaCl和KCl的量。两个模型化合物，分别用于表示冠醚保护基和轮烷的轴。对CDCl 3中的轮烷-阳离子络合物进行了二维NMR分析。我们发现，与B18C6相比，宿主轮烷在转移高氯酸盐时效果较差，但它们从1
• Pumping a Ring-Sliding Molecular Motion by a Light-Powered Molecular Motor
  作者：Jing-Jing Yu、Li-Yang Zhao、Zhao-Tao Shi、Qi Zhang、Gabor London、Wen-Jing Liang、Chuan Gao、Ming-Ming Li、Xiao-Ming Cao、He Tian、Ben L. Feringa、Da-Hui Qu

  DOI：10.1021/acs.joc.9b00783

  日期：2019.5.3

  Designing artificial molecular machines to execute complex mechanical tasks, like coupling rotation and translation to accomplish transmission of motion, continues to provide important challenges. Herein, we demonstrated a novel molecular machine comprising a second-generation light-driven molecular motor and a bistable [1]rotaxane unit. The molecular motor can rotate successfully even in an interlocked

  设计人造分子机器来执行复杂的机械任务，例如耦合旋转和平移以完成运动的传递，仍然面临着重要的挑战。在这里，我们展示了一种新型的分子机器，该机器包括第二代光驱动分子马达和双稳态[1]轮烷单元。即使在互锁的[1]轮烷体系中，分子电动机也可以通过光诱导的顺-反异构化和热螺旋反转而成功旋转，从而导致[1]轮烷的伴随过渡运动。通过1 H NMR，1 H– 1阐明了传输过程H COSY，HMQC，HMBC和2D ROESY NMR光谱，紫外可见吸收光谱和密度泛函理论计算。这是分子电动机逆转构成轮烷的二苯并24-冠-8和N-甲基三唑鎓部分之间明显非共价相互作用而旋转的第一个证明，显示了分子电动机执行更复杂任务的运行能力。
• Structure−Function Relationship of Amino Acid−[2]Rotaxanes
  作者：Inese Smukste、David B. Smithrud

  DOI：10.1021/jo026530q

  日期：2003.4.1

  Synthetic methodology was developed to construct amino acid-[2]rotaxanes that have phenylalanine and 3,5-di-tert-butylbenzene as blocking groups and dibenzo-24-crown-8, derivatized with either N-acetylargininyl or a carboxylic group, as the ring. A relative measure of the intramolecular interaction energies between the functional groups in DMSO/water mixtures is obtained by comparing their pK(a) values. Rotaxane structures were investigated through 2D NMR analysis and molecular dynamics simulations. Association constants for complexes of amino acids and rotaxanes in various protonation states were determined in a variety of solvent systems by H-1 NMR analysis. The unique intracomponent interactions that exist in the rotaxanes and their ability to act as artificial receptors are discussed.