(2R)-2-[[2-[6-[2-[[(1R)-1-carboxy-2-sulfanylethyl]amino]-2-oxoethoxy]naphthalen-2-yl]oxyacetyl]amino]-3-sulfanylpropanoic acid | 1191886-70-0

• 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: (2R)-2-[[2-[6-[2-[[(1R)-1-carboxy-2-sulfanylethyl]amino]-2-oxoethoxy]naphthalen-2-yl]oxyacetyl]amino]-3-sulfanylpropanoic acid
• CAS: 1191886-70-0
• 化学式: C₂₀H₂₂N₂O₈S₂
• 分子量: 482.535
• InChiKey: UZLVASTUSFRUEE-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  153
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,2'R)-2,2'-(1,3,6,8-tetraoxobenzo[lmn][3,8]phenanthroline-2,7-(1H,3H,6H,8H)-diyl)bis(3-mercaptopropanoic acid) 、 (2R)-2-[[2-[6-[2-[[(1R)-1-carboxy-2-sulfanylethyl]amino]-2-oxoethoxy]naphthalen-2-yl]oxyacetyl]amino]-3-sulfanylpropanoic acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 120.0h， 以60%的产率得到(7R,12R,29R,34R)-5,14,27,36,43,44-hexaoxo-16,25-dioxa-9,10,31,32-tetrathia-6,13,28,35-tetrazaheptacyclo[33.7.1.16,40.117,21.120,24.04,41.037,42]hexatetraconta-1(42),2,4(41),17(46),18,20,22,24(45),37,39-decaene-7,12,29,34-tetracarboxylic acid
  参考文献：
  名称：

  Amplifying Different [2]Catenanes in an Aqueous Donor−Acceptor Dynamic Combinatorial Library

  摘要：

  Two donor-acceptor [2]catenanes have been synthesized and characterized from a single dynamic combinatorial library in water. One of these catenanes is different from earlier related interlocked molecules in that two donor units stack on each other in an unexpected order. Shifting the equilibrium by choosing the right conditions resulted in a significant increase in the yields of the individual catenanes.

  DOI：

  10.1021/ja906634h
• 作为产物：
  描述：

  (2R,2'R)-2,2'-((2,2'-(naphthalene-2,6-diylbis(oxy))bis(acetyl))bis(azanediyl))bis(3-(tritylthio)propanoic acid) 在 三氟乙酸 、 三乙基硅烷 作用下， 反应 4.5h， 以78%的产率得到(2R)-2-[[2-[6-[2-[[(1R)-1-carboxy-2-sulfanylethyl]amino]-2-oxoethoxy]naphthalen-2-yl]oxyacetyl]amino]-3-sulfanylpropanoic acid
  参考文献：
  名称：

  Amplifying Different [2]Catenanes in an Aqueous Donor−Acceptor Dynamic Combinatorial Library

  摘要：

  Two donor-acceptor [2]catenanes have been synthesized and characterized from a single dynamic combinatorial library in water. One of these catenanes is different from earlier related interlocked molecules in that two donor units stack on each other in an unexpected order. Shifting the equilibrium by choosing the right conditions resulted in a significant increase in the yields of the individual catenanes.

  DOI：

  10.1021/ja906634h

文献信息

• High-Yielding Synthesis of Chiral Donor–Acceptor Catenanes
  作者：Mehrafarin Eilbigi Dehkordi、Vijay Luxami、G. Dan Pantoş

  DOI：10.1021/acs.joc.8b01629

  日期：2018.10.5

  We report the synthesis of [2]catenanes (Hopf links) in water utilizing disulfides and aromatic donor–acceptor interactions. The electron-rich dialkoxynaphthalene (DN) building blocks interact with electron-deficient naphthalenediimide (NDI) moieties connected by a polyamine chain. We study the effect of the polyamine linkers on the behavior of the library. The polyamine’s length and the number of

  我们报道了利用二硫化物和芳香族供体-受体相互作用在水中合成[2] catenanes（霍夫链）的方法。富电子的二烷氧基萘（DN）构件与通过多胺链连接的缺电子的萘二酰亚胺（NDI）部分相互作用。我们研究了多胺接头对文库行为的影响。多胺的长度和链中氮原子的数量会影响文库的分布，在某些情况下会导致链烷烃的组装，产率高达93％。
• Dynamic Combinatorial Donor−Acceptor Catenanes in Water: Access to Unconventional and Unexpected Structures
  作者：Ho Yu Au-Yeung、G. Dan Pantoş、Jeremy K. M. Sanders

  DOI：10.1021/jo101981p

  日期：2011.3.4

  describe here the assembly of new types of donor−acceptor [2]catenanes from dynamic combinatorial libraries (DCL) in water. These new catenanes contain both the donor and acceptor components in at least one of the interlocked rings, thereby possessing unusual and unexpected DAAD or DADD stacking sequences of the π units in their structures. The efficiency of the catenane assembly process can be enhanced

  我们在这里描述了从水中的动态组合库（DCL）组装新型供体-受体[2]邻苯二酚的过程。这些新的链烯在至少一个互锁的环中同时含有供体和受体成分，从而在其结构中具有异常和意外的DAAD或DADD堆积序列。可以通过多种方式操纵DCL平衡来提高链烷烃组装过程的效率：添加客体，改变构件的化学计量比或增加库浓度或溶剂的离子强度。发现链烷的形成及其组成取决于供体构件的几何形状，尺寸和柔韧性的细微差异。
• Templated Dynamic Synthesis of a [3]Catenane
  作者：Fabien B. L. Cougnon、Nicholas A. Jenkins、G. Dan Pantoş、Jeremy K. M. Sanders

  DOI：10.1002/anie.201106885

  日期：2012.2.6

  Three rings: The self‐assembly of a water‐soluble [3]catenane from a library composed of two linear building blocks, both terminated by cysteine components, is promoted either by a high salt concentration or by the presence of spermine. The spermine‐templated synthesis of the [3]catenane shows that such structures can exhibit strong binding interactions with a biologically relevant target in water

  三个环：高盐浓度或精胺的存在促进了由两个线性结构单元组成的库中水溶性[3]环烷的自组装，两个线性结构单元均由半胱氨酸成分终止。以精胺为模板的[3]环烷的合成表明，在近乎生理条件下，此类结构可与水中的生物学相关靶标表现出较强的结合相互作用。
• Exploring the Formation Pathways of Donor−Acceptor Catenanes in Aqueous Dynamic Combinatorial Libraries
  作者：Fabien B. L. Cougnon、Ho Yu Au-Yeung、G. Dan Pantoş、Jeremy K. M. Sanders

  DOI：10.1021/ja111407m

  日期：2011.3.9

  The discovery through dynamic combinatorial chemistry (DCC) of a new generation of donor-acceptor [2]catenanes highlights the power of DCC to access unprecedented structures. While conventional thinking has limited the scope of donor-acceptor catenanes to strictly alternating stacks of donor (D) and acceptor (A) aromatic units, DCC is demonstrated in this paper to give access to unusual DAAD, DADD

  通过动态组合化学 (DCC) 发现的新一代供体-受体 [2] 链烷突显了 DCC 获得前所未有结构的能力。虽然传统思维将供体-受体链环的范围限制为严格交替的供体 (D) 和受体 (A) 芳族单元堆叠，但本文证明了 DCC 可以访问不寻常的 DAAD、DADD 和 ADAA 堆叠。这些链中的每一个都有特定的结构要求，可以控制它们的形成。在这些结果的基础上，并在观察到链环代表反应途径中的动力学瓶颈的基础上，我们提出了一种解释和预测所形成结构的机制。此外，
• Amplifying Different [2]Catenanes in an Aqueous Donor−Acceptor Dynamic Combinatorial Library
  作者：Ho Yu Au-Yeung、G. Dan Pantoş、Jeremy K. M. Sanders

  DOI：10.1021/ja906634h

  日期：2009.11.11

  Two donor-acceptor [2]catenanes have been synthesized and characterized from a single dynamic combinatorial library in water. One of these catenanes is different from earlier related interlocked molecules in that two donor units stack on each other in an unexpected order. Shifting the equilibrium by choosing the right conditions resulted in a significant increase in the yields of the individual catenanes.