syn-9-nitro-2,11-dithia[3.3]methacyclophane | 55323-87-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: syn-9-nitro-2,11-dithia[3.3]methacyclophane
• 英文别名: syn-9-nitro-2,11-dithia[3.3]metacyclophane；9-Nitro-2,11-dithia<3.3>metabenzenophan；9-Nitro-2,11-dithia[3.3]metabenzenophan；17-Nitro-3,11-dithiatricyclo[11.3.1.15,9]octadeca-1(17),5(18),6,8,13,15-hexaene
• CAS: 55323-87-0
• 化学式: C₁₆H₁₅NO₂S₂
• 分子量: 317.433
• InChiKey: MROYCGOHGBXQSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  96.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  syn-9-nitro-2,11-dithia[3.3]methacyclophane 在 palladium on activated charcoal sodium azide 、 硫酸 、 氢气 、 sodium nitrite 作用下， 以 丙酮 、 苯 为溶剂， 反应 3.51h， 生成 17-Azido-3,11-dithiatricyclo[11.3.1.15,9]octadeca-1(17),5(18),6,8,13,15-hexaene
  参考文献：
  名称：

  Moriguchi, Tetsuji; Sakata, Kazunori; Tsuge, Akihiko, Journal of Chemical Research, Miniprint, 1999, # 10, p. 2601 - 2609

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-双(溴甲基)-2-硝基苯 以51%的产率得到
  参考文献：
  名称：

  VOEGTLE F.; GRUETZE J.; NAETSCHER R.; WIEDER W.; WEBER E.; GRUEN R., CHEM. BER. , 1975, 108, NO 5, 1694-1711

  摘要：

  DOI：

文献信息

• Conformational and Intramolecular Hydrogen-Bonding Properties of Substituted Dithia[3.3]metacyclophanes
  作者：Tetsuji Moriguchi、Kazunori Sakata、Akihiko Tsuge

  DOI：10.1246/cl.1999.167

  日期：1999.2

  Conformational properties and intramolecular hydrogen-bondings of dithia[3.3]metacyclophanes carrying one or two amino group on their internal positions were studied by 1H-NMR, IR spectra and X-ray structural analyses. It was found out that intramolecular hydrogen-bonding network between amino protons and bridge sulfur atoms is formed and it is closely related to the conformations of cyclophanes.

  通过1H-NMR、IR光谱和X射线结构分析研究了在其内部位置带有一个或两个氨基的二硫杂[3.3]环芳烃的构象特性和分子内氢键。发现氨基质子与桥硫原子之间形成了分子内氢键网络，它与环芳的构象密切相关。
• Intra- and intermolecular interactions in substituted dithia[3.3]metacyclophanes
  作者：Tetsuji Moriguchi、Kazunori Sakata、Akihiko Tsuge

  DOI：10.1039/b100285f

  日期：——

  The conformational properties of and intramolecular hydrogen-bonding in dithia[3.3]metacyclophanes carrying one or two amino groups on their internal positions were examined by their 1H-NMR and IR spectra and by X-ray structural analyses. It was suggested that an intramolecular hydrogen-bonding network between the amino protons and bridge sulfur atoms is closely related to the conformations of the cyclophanes. Crystal structural analyses of dithia[3.3]metacyclophanes carrying an amino and a nitro group on their internal positions were also carried out. It has been found that the molecules assemble as one-dimensional array columns in the crystal owing to the intermolecular π–π interaction and this columnar structure is deformed by the occurrence of intermolecular hydrogen-bonding.

  通过 1H-NMR 和红外光谱以及 X 射线结构分析，研究了内部位置带有一个或两个氨基的二硫杂[3.3]偏环烷的构象特性和分子内氢键。研究表明，氨基质子和桥硫原子之间的分子内氢键网络与环烷的构象密切相关。此外，还对内部位置带有氨基和硝基的二硫杂[3.3]偏环烷进行了晶体结构分析。研究发现，由于分子间的π-π相互作用，分子在晶体中组合成一维阵列柱，这种柱状结构会因分子间氢键的发生而变形。