N,N',N''-tris[2-(tert-butoxycarbonylamino)propionyl]-N'''-(3-carboxypropionyl)-1,6,20,25-tetraaza[6.1.6.1]paracyclophane | 866414-10-0

• 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: N,N',N''-tris[2-(tert-butoxycarbonylamino)propionyl]-N'''-(3-carboxypropionyl)-1,6,20,25-tetraaza[6.1.6.1]paracyclophane
• 英文别名: 4-Oxo-4-[12,22,27-tris[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-7,12,22,27-tetrazapentacyclo[26.2.2.23,6.213,16.218,21]octatriaconta-1(30),3(38),4,6(37),13(36),14,16(35),18,20,28,31,33-dodecaen-7-yl]butanoic acid；4-oxo-4-[12,22,27-tris[3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-7,12,22,27-tetrazapentacyclo[26.2.2.23,6.213,16.218,21]octatriaconta-1(30),3(38),4,6(37),13(36),14,16(35),18,20,28,31,33-dodecaen-7-yl]butanoic acid
• CAS: 866414-10-0
• 化学式: C₆₂H₈₃N₇O₁₂
• 分子量: 1118.38
• InChiKey: DNIRDQBPCAJPNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  81
• 可旋转键数：
  18
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  234
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N,N',N''-tris[2-(tert-butoxycarbonylamino)propionyl]-N'''-(3-carboxypropionyl)-1,6,20,25-tetraaza[6.1.6.1]paracyclophane 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以71%的产率得到2,5-dioxopyrrolidin-1-yl 4-oxo-4-(9,13,18-tris(3-((tert-butoxycarbonyl)amino)propanoyl)-4,9,13,18-tetraaza-1,3,10,12(1,4)-tetrabenzenacyclooctadecaphane-4-yl)butanoate
  参考文献：
  名称：

  Synthesis of Peptide-Based Cyclophane Oligomers Having Multivalently Enhanced Guest-Binding Affinity

  摘要：

  通过用赖氨酸和相应的赖氨酸肽作为支架，对四氮杂[6.1.6.1]对环芳烷的琥珀酰亚胺酯衍生物进行胺解反应，随后去除保护基团，制备了水溶性环芳烷二聚体、三聚体、四聚体和五聚体。与单环环芳烷相比，这些环芳烷寡聚体对6-对甲苯氨基萘-2-磺酸盐等荧光客体显示出增强的客体结合亲和力，反映了大环中的多价效应。通过表面等离子体共振（SPR）测量，也证实了多价大环对这些环芳烷寡聚体的客体结合的影响。

  DOI：

  10.1246/bcsj.20120076
• 作为产物：
  描述：

  1.6.20.25-四偶氮[6.1.6.1]环苯 在 N,N'-二环己基碳二亚胺 作用下， 生成 N,N',N''-tris[2-(tert-butoxycarbonylamino)propionyl]-N'''-(3-carboxypropionyl)-1,6,20,25-tetraaza[6.1.6.1]paracyclophane
  参考文献：
  名称：

  多位多环芳烃宿主的合成和客体结合研究

  摘要：

  通过分别连接两个或五个大环骨架，将新型的含葡萄糖苷的双（环烷）和含葡萄糖的五环（环烷）制备为水溶性主体。相对于相应的单环，本发明的双（环烷）和五（环）对疏水染料6-对甲苯二萘基萘-2-磺酸的客体结合亲和力分别提高了13-和1200-倍。环烷，反映了大环化合物的多价效应。

  DOI：

  10.1016/j.tetlet.2005.07.010

文献信息

• Synthesis of Cyclophane Dimer Using Cyclophane-tethered Fmoc-amino Acid Derivatives as a Multivalent Host
  作者：Osamu Hayashida、Tomomi Nakashima

  DOI：10.1246/cl.2011.134

  日期：2011.2.5

  Water-soluble cyclophane dimer was synthesized by Fmoc-chemistry of cyclophane-tethered Fmoc-lysine derivative, as a multivalent host. The host showed enhanced guest binding affinity relative to that by monocyclic cyclophane, as confirmed by fluorescence spectroscopy as well as surface plasmon resonance measurements.

  通过Fmoc化学合成了水溶性环烯烃二聚体，作为一种多价宿主。这种宿主相对于单环环烯烃显示出更强的客体结合亲和力，使用荧光光谱和表面等离子共振测量进行了确认。
• Stimuli-Responsive Supramolecular Coaggregation and Disaggregation of Host–Guest Conjugates Having a Disulfide Linkage
  作者：Osamu Hayashida、Kana Shibata

  DOI：10.1021/acs.joc.0c00237

  日期：2020.4.17

  formed spontaneously through host–guest complexation. As regard the supramolecular coaggregates, the existence of larger particles was confirmed by DLS measurements and TEM observation. The hydrophobic interaction between the dabsyl moiety and macrocyclic cavity and electrostatic interactions between 1a and 2a play important roles in the supramolecular coaggregate formation. Each cyclophane having a cleavable

  合成了具有带二硫键可裂解键的dabsyl的水溶性阳离子和阴离子环烷（分别为1a和2a）作为与客体和客体组分共价结合的主体-客体共轭物。在水介质中，每个环烷都观察到自包含现象，但没有自聚集行为。每个环烷烃通过疏水相互作用在其大环腔（主体组分）中包括其自己的dabsyl部分（来宾组分）。当1当量。的阳离子1a被添加到阴离子2a的水溶液中然而，超分子聚集体是通过宿主-客体复合而自发形成的。关于超分子聚集体，通过DLS测量和TEM观察证实了较大颗粒的存在。dabsyl部分和大环腔之间的疏水相互作用以及1a和2a之间的静电相互作用在超分子共聚集体形成中起重要作用。通过MALDI-TOF MS证实，通过还原剂（例如DTT），每个具有可裂解的二硫键的环烷都可以轻松转化为相应的硫醇。由1a和2a组成的超分子聚集体的分解加入DTT成功地进行了操作，释放了达布西尔的硫醇衍生物。聚集体的这种分解也由其他外部刺激如盐和竞争性客体进行。
• Preparation and Multivalently Enhanced Guest-Binding Affinity of Water-Soluble Cyclophane Heptadecamers
  作者：Osamu Hayashida、Daisuke Sato

  DOI：10.1021/jo800129j

  日期：2008.4.1

  Water-soluble cyclophane heptadecamers (17a and 17b), which were constructed with the core cyclophane heptadecamer and 36 polar side chains with a terminal galactose or glucose residue, respectively, were prepared. An analogous cyclophane pentamer (5a) was also prepared. The stoichiometry for the complex of the cyclophane oligomers with fluorescence guests such as TNS was confirmed to be 1:1 host:guest by a Job plot. The guest-binding affinity of cyclophane heptadecamers 17a and 17b was much enhanced relative to that of a corresponding monocyclic cyclophane (1a), i.e., the 1:1 binding constant (K) values for 17a with TNS, 2,6-ANS, and 1,8-ANS were ca. 1700-, 1600-, and 1500-fold larger than those of 1a for the identical guests, respectively, which reflects the multivalency effects in macrocycles. Meanwhile, the corresponding K values for the cyclophane pentamer 5a with TNS, 2,6-ANS, and 1,8-ANS were ca. 250-, 250-, and 110-fold larger than those of 1a for the identical guest, respectively.