5-Methoxy-1,3-benzoldimethanthiol | 124537-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-Methoxy-1,3-benzoldimethanthiol
• 英文别名: 3,5-bis(mercaptomethyl)anisole；[3-Methoxy-5-(sulfanylmethyl)phenyl]methanethiol
• CAS: 124537-05-9
• 化学式: C₉H₁₂OS₂
• 分子量: 200.326
• InChiKey: GXZLCQXSSLAWEE-UHFFFAOYSA-N

物化性质

• 沸点：
  335.1±32.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  11.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Methoxy-1,3-benzoldimethanthiol 在 氢氧化钾 、 三甲氧基磷 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.0h， 生成 anti-5,13-Dimethoxy<2,2>metacyclophan
  参考文献：
  名称：

  Chinone. XIII. Synthese von 4,5,9,10-Tetrahydropyren-2,7-dion und Versuch zur Darstellung von Pyren-2,7-dion

  摘要：

  The titel quinones 7 and 9 are of interest as electron acceptors for organic conductors. The synthesis of their conjugate hydroquinones 6 and 8 via the metacyclophane derivative 3 is described. The tetrahydropyrene-2,7-dione 7 - obtained by oxidation of 6 - possesses only a limited stability, whereas pyrene-2,7-dion (9) proved to unstable to be isolated.

  DOI：

  10.1002/prac.19943360203
• 作为产物：
  描述：

  在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 5-Methoxy-1,3-benzoldimethanthiol
  参考文献：
  名称：

  Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure

  摘要：

  Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-alpha,alpha'-dithiol (9), p-xylene-alpha,alpha'-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide Bb or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol as with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by H-1 NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex.

  DOI：

  10.1021/jo950957y

文献信息

• 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。
• Syntheses, structural properties, and charge-transfer complexes of pyrenophanes
  作者：Akihiko Tsuge、Megumi Otsuka、Tetsuji Moriguch、Kazunori Sakata

  DOI：10.1039/b509719c

  日期：——

  benzene components has been confirmed for the pyrenophanes having the substituent at the outer position of the opposite benzene ring (perpendicular conformation). The NH-pi interaction between the inner amino group on the opposite benzene ring and the pyrene ring was observed. Formation of charge-transfer complexes of the pyrenophanes and tetracyanoethylene (TCNE) was performed. It has been found out

  制备了在苯环的内部位置或外部位置带有各种官能团的Dithia [3.3]（4,9）苯并吡喃庚烷。在相对的苯环的内部位置具有取代基的吡喃芬酮显示出the和苯成分以平行方式（平行构象）存在的构象。相反，对于在相对的苯环的外部位置具有取代基的吡咯烷酮，已经确认了以the和苯成分的垂直取向为特征的构象（垂直构象）。观察到相对苯环上的内部氨基与the环之间的NH-pi相互作用。进行了庚烯和四氰基乙烯（TCNE）的电荷转移复合物的形成。
• Spectral Properties and Charge-transfer Complexes of the Cyclophanes Having the Pyrene Moiety
  作者：Akihiko Tsuge、Yukihiro Ikeura、Tetsuji Moriguchi、Minoru Yamaji

  DOI：10.1246/cl.2007.1016

  日期：2007.8.5

  cyclophanes having the pyrene moiety have been synthesized. The fluorescence and phosphorescence properties have been examined in terms of their structure. It has been found out that their charge-transfer complexes reflect the transannular π-π interaction based on the structure.

  已经合成了具有芘部分的新型环芳。已经根据它们的结构检查了荧光和磷光特性。已经发现它们的电荷转移复合物反映了基于结构的跨环π-π相互作用。
• 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。
• Synthesis of functionalised cyclophanes with cage structure; via an unusual termolecular collision
  作者：Perumal Rajakumar、Arunachalam Kannan

  DOI：10.1016/s0040-4039(00)61420-x

  日期：1993.12

  Coupling of the tetrathiol 11 with two equivalents of the dibromide 6,7 and 8 under high dilution technique in the presence of KOH in benzene - ethanol afforded the cyclophanes 1a, 1c & 1b respectively. Similarly cyclophane 1d was obtained from the tetrathiol 11 and tetrabromide 9.