1,8-diisothiocyanatoanthracene | 934974-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,8-diisothiocyanatoanthracene
• CAS: 934974-55-7
• 化学式: C₁₆H₈N₂S₂
• 分子量: 292.385
• InChiKey: FNYYNGKBODVGKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,8-diisothiocyanatoanthracene 、 L-phenylalanine n-butyl ester hydrochloride 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Chiral Recognition of Carboxylates by a Static Library of Thiourea Receptors with Amino Acid Arms

  摘要：

  Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and alpha-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.

  DOI：

  10.1021/acs.joc.5b00403
• 作为产物：
  描述：

  1,8-二氨基蒽醌 在 sodium tetrahydroborate 、 碳酸氢钠 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 12.5h， 生成 1,8-diisothiocyanatoanthracene
  参考文献：
  名称：

  Chiral Recognition of Carboxylates by a Static Library of Thiourea Receptors with Amino Acid Arms

  摘要：

  Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and alpha-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.

  DOI：

  10.1021/acs.joc.5b00403

文献信息

• Enantioselective recognition of sodium carboxylates by an 1,8-diaminoanthracene based ion pair receptor containing amino acid units
  作者：Paulina Cios、Jan Romański

  DOI：10.1016/j.tetlet.2016.07.053

  日期：2016.8

  An anthracene based ion pair receptor containing two amino acid units supported by cation and anion binding domains has been synthesized and shown to exhibit enhanced anion binding affinities in the presence of sodium cations. The receptor’s ability to recognize enantiomers was studied using chiral carboxylates derived from 2-phenylbutyric acid, mandelic acid, and three Boc-protected amino acids. Sodium

  已经合成了包含两个由阳离子和阴离子结合结构域支持的氨基酸单元的蒽基离子对受体，并显示在钠阳离子存在下显示出增强的阴离子结合亲和力。使用衍生自2-苯基丁酸，扁桃酸和三个Boc保护的氨基酸的手性羧酸盐，研究了受体识别对映体的能力。钠阳离子配位不会影响手性识别，但会影响阴离子结合的强度。对于钠离子，在钠阳离子存在下阴离子结合的最大增强被发现，对于Boc- N-色氨酸，发现最大的对映异构。阴离子和盐结合的比较研究表明，受体结构中多个结合域的同时作用与单载体受体2相比，其1具有更强的盐缔合和更好的对映选择性。
• Synthesis and Evaluation of a Pseudocyclic Tristhiourea-Based Anion Host
  作者：Adi Dahan、Tali Ashkenazi、Vladimir Kuznetsov、Svetlana Makievski、Eyal Drug、Ludmila Fadeev、Maayan Bramson、Sari Schokoroy、Emily Rozenshine-Kemelmakher、Michael Gozin

  DOI：10.1021/jo061774m

  日期：2007.3.1

  A novel methodology for the evaluation of receptor arrangement in structurally flexible anion chemosensors was developed and applied to map the binding site of a new pseudocyclic tristhiourea chemosensor ( 6). The syntheses of 6 and related macrocyclic chemosensor 10 ( a model of the folded monomeric structure of 6) are reported. Both chemosensors were evaluated by titration with a variety of structurally different anions in CH3Cl and DMSO, showing a common preference for F-, CH3CO2-, and H2PO4-. However, within this group of anions, the binding patterns of the chemosensors differed, indicating dissimilarity in the arrangement of the binding sites of 6 and 10.
• Chiral Recognition of Carboxylates by a Static Library of Thiourea Receptors with Amino Acid Arms
  作者：Filip Ulatowski、Janusz Jurczak

  DOI：10.1021/acs.joc.5b00403

  日期：2015.5.1

  Chiral recognition is based on a large network of very subtle interactions whose outcome is difficult to predict. A combinatorial approach is therefore the most suitable to search for the most efficient receptor and obtain a structure-enantioselectivity correlation. We synthesized a set of 12 receptors constructed with 1,9-diaminoantracene and alpha-amino acid esters, linked via thiourea groups. The association constants and enantioselectivities for the complexes with mandelate and N-acetylphenylalanine were determined by competitive NMR titrations. Association constants quite regularly depend on the substituents in the receptor structure, but the distribution of enantioselectivities across the library could not easily be rationalized.