| 1049755-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• CAS: 1049755-85-2
• 化学式: C₃₁H₂₀O₆S₂
• 分子量: 552.628
• InChiKey: CRXNVBZWBGBUFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  39.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 喹啉 、 铜 作用下， 反应 0.33h， 以40%的产率得到3,25-Dioxa-29,31-dithiaheptacyclo[25.5.1.04,13.07,12.015,24.016,21.030,33]tritriaconta-1(32),4(13),5,7,9,11,15(24),16,18,20,22,27,30(33)-tridecaene
  参考文献：
  名称：

  Oxa-bridged cyclophanes featuring thieno[2,3-b]thiophene and C2-symmetric binol or bis-naphthol rings: synthesis, structures, and conformational studies

  摘要：

  Oxa-bridged cyclophanes 4/6 and 8/10 featuring thieno[2,3-b]thiophene ring and binol or bis-naphthol have been synthesized. The Structures are assigned by 2D NMR data and the identity of 4 is also independently established by a single X-ray crystallography. From dynamic NMR analysis, the Arrhenius energy of activation Delta G(#) for bridge inversions in 4 and 6 was calculated to be 15.3 and 12.9 kcal/mol, respectively. A higher Delta G(#) for 4, relative to the ester free 6 is attributable to the steric compression stemming from C2/C5 ester substituents to the bridge inversion processes. While the methylene bridges undergo inversion in 4 and 6, the naphthyl-naphthyl pseudo-rotation appears to be restricted even at higher temperatures. This is Supported by retention of the optical purity of the chiral (-) 4 under thermal condition. For the case of bis-naphthol cyclophane 8, we observed the flipping of both the -OCH2- and the naphthyl-CH2-naphthyl bridges with Delta G(#) of ca. 11.4 kcal/mol. However, the ester free cyclophane 10 remained conformationally mobile even at -55 degrees C and its AGO was assumed to be <11.4 kcal/mol. The presence of an extra -CH2- linker in bis-naphthol cyclophanes 8/10 renders them relatively more conformationally mobile compared to binol cyclophanes 4/6, possessing a rigid naphthyl-naphthyl geometry. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.076
• 作为产物：
  描述：

  Diethyl 3,25-dioxa-29,31-dithiaheptacyclo[25.5.1.04,13.07,12.015,24.016,21.030,33]tritriaconta-1(32),4(13),5,7,9,11,15(24),16,18,20,22,27,30(33)-tridecaene-28,32-dicarboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以66%的产率得到
  参考文献：
  名称：

  Oxa-bridged cyclophanes featuring thieno[2,3-b]thiophene and C2-symmetric binol or bis-naphthol rings: synthesis, structures, and conformational studies

  摘要：

  Oxa-bridged cyclophanes 4/6 and 8/10 featuring thieno[2,3-b]thiophene ring and binol or bis-naphthol have been synthesized. The Structures are assigned by 2D NMR data and the identity of 4 is also independently established by a single X-ray crystallography. From dynamic NMR analysis, the Arrhenius energy of activation Delta G(#) for bridge inversions in 4 and 6 was calculated to be 15.3 and 12.9 kcal/mol, respectively. A higher Delta G(#) for 4, relative to the ester free 6 is attributable to the steric compression stemming from C2/C5 ester substituents to the bridge inversion processes. While the methylene bridges undergo inversion in 4 and 6, the naphthyl-naphthyl pseudo-rotation appears to be restricted even at higher temperatures. This is Supported by retention of the optical purity of the chiral (-) 4 under thermal condition. For the case of bis-naphthol cyclophane 8, we observed the flipping of both the -OCH2- and the naphthyl-CH2-naphthyl bridges with Delta G(#) of ca. 11.4 kcal/mol. However, the ester free cyclophane 10 remained conformationally mobile even at -55 degrees C and its AGO was assumed to be <11.4 kcal/mol. The presence of an extra -CH2- linker in bis-naphthol cyclophanes 8/10 renders them relatively more conformationally mobile compared to binol cyclophanes 4/6, possessing a rigid naphthyl-naphthyl geometry. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.076