1,4-Naphthalindimethanthiol | 59045-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-Naphthalindimethanthiol
• 英文别名: 1,4-Bis(mercaptomethyl)naphthalene；1,4-Naphthalenedimethanethiol；[4-(sulfanylmethyl)naphthalen-1-yl]methanethiol
• CAS: 59045-58-8
• 化学式: C₁₂H₁₂S₂
• 分子量: 220.359
• InChiKey: VNEORWMTZORVHV-UHFFFAOYSA-N

物化性质

• 熔点：
  68-78 °C
• 沸点：
  397.0±22.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-Naphthalindimethanthiol 在 三氯化锑 、 N,N-二异丙基乙胺 、 三溴化磷 作用下， 以 氯仿 、 1,1,2,2-四氯乙烷 为溶剂， 反应 73.5h， 生成 2,13,15,26,27,38-Hexathia-1,14-diphosphaoctacyclo[12.12.12.24,11.217,24.229,36.05,10.018,23.030,35]tetratetraconta-4(44),5,7,9,11(43),17(42),18,20,22,24(41),29(40),30,32,34,36(39)-pentadecaene
  参考文献：
  名称：

  超分子的“重金属化”导致异常的自组装P2L3加密

  摘要：

  与旧的相伴，与新的相伴：金属-有机超分子组装体的重金属化能导致新的结构类型吗？据报道，一系列含Bi，Sb和As的穴状配体可以进行金属转移，以生成新型的P 2 L 3穴状配体（参见方案）。在P  S键表现可逆，像传统的金属-配体键，表明动态共价化学的一个可能的新基序。

  DOI：

  10.1002/anie.200906460
• 作为产物：
  描述：

  1,4-双(溴甲基)萘 在 sodium hydroxide 、 硫脲 作用下， 生成 1,4-Naphthalindimethanthiol
  参考文献：
  名称：

  Structural Characterization of Thiocyclophanes That Promote Edge-to-Face Aromatic-Aromatic Geometries

  摘要：

  Several [4.4]thiocyclophanes have been examined in solution and the solid state. These molecules contain two aromatic units, phenyl and/or naphthyl, with linking chains attached meta or para on the phenyl groups, and 1,3 or 1,4 on the naphthyl groups. Most previous studies of cyclophanes containing two aromatic rings have focused on enforcing parallel alignment of those rings. The molecules discussed here, in contrast, were chosen to promote edge-to-face juxtapositions. Crystallographic data confirm that edge-to-face orientations between the linked aromatic groups are available for these cyclophanes, and H-1 NMR data indicate that conformations containing these orientations are populated in solution. These cyclophanes provide spectroscopic references for NMR-based studies of folding in more flexible diphenyl and dinaphthyl compounds.

  DOI：

  10.1021/jo00118a030

文献信息

• Chloride-catalyzed, multicomponent self-assembly of arsenic thiolates
  作者：Matthew E. Carnes、Mary S. Collins、Nathan R. Lindquist、Edmundo Guzmán-Percástegui、Michael D. Pluth、Darren W. Johnson

  DOI：10.1039/c3cc47093h

  日期：——

  We present the observation that chloride serves as a simple catalyst for the acceleration of a self-assembly reaction between AsCl3 and dithiolate ligands (H2L) to form As2L3 assemblies. Studies on a model monomeric arsenic complex suggest that chloride may accelerate ligand exchange dynamics in pnictogen thiolates in general.

  我们观察到氯化物作为一种简单催化剂，加速了AsCl3与二硫配体（H2L）之间的自组装反应，从而形成As2L3组装体。对一种单体砷配合物的研究表明，氯化物可能普遍加速轻元素硫代配体的配体置换动力学。
• Self-Assembled E₂L₃ Cryptands (E = P, As, Sb, Bi): Transmetalation, Homo- and Heterometallic Assemblies, and Conformational Isomerism
  作者：Virginia M. Cangelosi、Timothy G. Carter、Justin L. Crossland、Lev N. Zakharov、Darren W. Johnson

  DOI：10.1021/ic1012186

  日期：2010.11.1

  increasing size of the Group 15 element. Finally, it is reported that if two metals are present during the self-assembly process, heterometallic cryptands form. These supramolecular cryptands are reminiscent of their organic analogues, but result from a self-assembly process rather than a stepwise synthesis. Surprisingly, they possess conformational isomerism and exhibit dynamic transmetalation in their reactivity

  通过将卤化碳卤化物与二硫醇盐进行自组装，制备了一系列含第15组的同金属（E 2 L 3，E = P，As，Sb，Bi）和杂金属（AsSbL 3，AsBiL 3，PSbL 3）超分子穴状配体。配体或通过较重同源物直接重金属化。单晶X射线衍射的结构表征表明，光生原的身份显着影响了ES键距离和ES键角度。1 H NMR光谱显示，均金属的穴状配体在溶液中是动态的：令人惊讶的是，一个配体“翻转”，干扰了C 3复杂的对称性，并给出一个新的不对称构象异构体。对配体的对称和不对称构象进行密度泛函理论计算，并将能量与通过NMR光谱观察到的能量进行比较。已经发现，不对称穴状配体与其对称构象异构体的相对稳定性随第15族元素尺寸的增加而增加。最后，据报道，如果在自组装过程中存在两种金属，则会形成杂金属配合物。这些超分子的穴状分子让人想起它们的有机类似物，但它们是自组装过程而不是逐步合成的结果。出人意料的是，它们具
• SYNTHESIS OF CYCLOPHANES FROM A SELF-ASSEMBLY REACTION
  申请人：University of Oregon

  公开号：US20160137598A1

  公开（公告）日：2016-05-19

  Disclosed herein is a novel method for preparing cyclophanes, comprising forming a disulfide cyclophane by contacting a linker moiety which includes two or more thiol groups, with a metal salt and an oxidant. The disulfide cyclophane is then desulfurized to form a thiacyclophane comprising thioether bridges. This thiacyclophane optionally may be further desulfurized to form an unsaturated hydrocarbon cyclophane, which can then be reduced to form a saturated hydrocarbon cyclophane. The various cyclophanes can be synthesized in a ring form, such as a dimer, trimer or tetramer etc., or they can be synthesized in a tetrahedral or larger structure. Also disclosed are novel cyclophanes formed by the disclosed method.

  本文揭示了一种制备环戊烷的新方法，包括通过将含有两个或更多硫醚基团的连接剂与金属盐和氧化剂接触来形成二硫化环戊烷。然后对二硫化环戊烷进行脱硫作用，形成含有硫醚桥的硫代环戊烷。这种硫代环戊烷可以选择性地进一步脱硫，形成不饱和碳氢化合物环戊烷，然后可以还原为饱和碳氢化合物环戊烷。这些不同的环戊烷可以以环形形式合成，如二聚体、三聚体或四聚体等，或者它们可以以四面体或更大的结构合成。此外，还披露了通过上述方法形成的新型环戊烷。
• Copper(<scp>ii</scp>) serves as an efficient additive for metal-directed self-assembly of over 20 thiacyclophanes
  作者：Ngoc-Minh Phan、Lev N. Zakharov、Darren W. Johnson

  DOI：10.1039/c8cc08095j

  日期：——

  Cu2+ salts are presented as an alternative to previously reported pnictogen additives in the self-assembly of 23 different thiacyclophanes. This process allows for further tuning of library equilibrium mixtures: for instance, by altering additive types and concentrations, trimeric macrocycles are amplified. These trimeric disulfides can then be covalently trapped to form 2 novel thioethers, highlighting

  在23种不同的噻唑烷酮的自组装过程中，Cu 2+盐可作为以前报道的光气添加剂的替代品。该过程允许进一步调节文库平衡混合物：例如，通过改变添加剂类型和浓度，可扩增三聚体大环化合物。然后可以将这些三聚体二硫键共价捕获以形成2个新的硫醚，突出显示了接近这些新的萘桥联环芳基的简便途径。
• Synthesis of cyclophanes for a self-assembly reaction
  申请人：University of Oregon

  公开号：US10344005B2

  公开（公告）日：2019-07-09

  Disclosed herein is a novel method for preparing cyclophanes, comprising forming a disulfide cyclophane by contacting a linker moiety which includes two or more thiol groups, with a metal salt and an oxidant. The disulfide cyclophane is then desulfurized to form a thiacyclophane comprising thioether bridges. This thiacyclophane optionally may be further desulfurized to form an unsaturated hydrocarbon cyclophane, which can then be reduced to form a saturated hydrocarbon cyclophane. The various cyclophanes can be synthesized in a ring form, such as a dimer, trimer or tetramer etc., or they can be synthesized in a tetrahedral or larger structure. Also disclosed are novel cyclophanes formed by the disclosed method.

  本文公开了一种制备环烷的新方法，该方法包括将包含两个或两个以上硫醇基团的连接分子与金属盐和氧化剂接触，形成二硫化环烷。然后将二硫化环烷脱硫，形成包含硫醚桥的硫代环烷。这种硫代环烷还可以进一步脱硫，形成不饱和烃环烷，然后再还原形成饱和烃环烷。各种环烷可合成为环状，如二聚体、三聚体或四聚体等，也可合成为四面体或更大的结构。同时公开的还有通过公开方法形成的新型环烷。