2,2,11,11-tetradeuterio-6,15-dimethoxy<3.3>metacyclophane | 121696-68-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2,11,11-tetradeuterio-6,15-dimethoxy<3.3>metacyclophane
• 英文别名: Tricyclo[11.3.1.15,9]octadeca-1(17),5,7,9(18),13,15-hexaene-3,3,11,11-d4, 7,15-dimethoxy-；3,3,11,11-tetradeuterio-7,15-dimethoxytricyclo[11.3.1.15,9]octadeca-1(17),5(18),6,8,13,15-hexaene
• CAS: 121696-68-2
• 化学式: C₂₀H₂₄O₂
• 分子量: 300.378
• InChiKey: RPKYKJXUMXPJPN-KHORGVISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,11,11-tetradeuterio-6,15-dimethoxy<3.3>metacyclophane 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 生成 12,12,21,21-tetradeuterio-1,4-dioxa-<4.3.3>(1,3,5)cyclophane
  参考文献：
  名称：

  Conformational analysis of 12,12,21,21-tetradeuterio-1,4-dioxa-[4.3.3](1,3,5)Cyclophane

  摘要：

  DOI：

  10.1016/s0040-4039(00)82324-2
• 作为产物：
  描述：

  1,3-二-(溴甲基)-5-甲氧基苯 在 偶氮二异丁腈 、 三氟化硼乙醚 、 oxonium 、 氘代三正丁基锡 作用下， 以 溶剂黄146 、 xylene 为溶剂， 生成 2,2,11,11-tetradeuterio-6,15-dimethoxy<3.3>metacyclophane
  参考文献：
  名称：

  Conformational analysis of 12,12,21,21-tetradeuterio-1,4-dioxa-[4.3.3](1,3,5)Cyclophane

  摘要：

  DOI：

  10.1016/s0040-4039(00)82324-2

文献信息

• Conformational analysis of [3.3]cyclophanes. 4. A conformational study of [3.3]metacyclophanes through variable-temperature proton NMR and optical rotation
  作者：Katsuya Sako、Teruo Shinmyozu、Hiroyuki Takemura、Masahiko Suenaga、Takahiko Inazu

  DOI：10.1021/jo00050a031

  日期：1992.11

  Conformational behavior of 2,2,11,11-tetradeuterio[3.3]metacyclophanes 1-d4 and 2-d4 has been studied by a variable-temperature (VT) H-1 NMR method. In order to simplify the interpretation of the H-1 NMR spectrum, four deuteriums were introduced at C-2 and C-11 positions of the trimethylene bridges of [3.3]metacyclophanes by reductive desulfurization of 2,11-bis(1,4-dithiabutane-1,4-diyl)[3.3]metacyclophanes 4 and 5 with tri-n-butyltin deuteride. Our previous conformational study of tetradeuterio-1,4-dioxa[4.3.3]cyclophane (3-d4) revealed that the temperature-dependent phenomenon in the H-1 NMR spectrum of 1 was ascribed to the inversion the trimethylene bridges. The work also suggested the presence of benzene ring inversion. To confirm this, optically active [3.3]metacyclophanechromium tricarbonyl complexes (-)- and (+)-17 were prepared by means of the HPLC separation of racemic complex (+/-)-17 using a chiral stationary phase. Racemization occurred when (-)- and (+)-17 were decomplexed at 20-degrees-C. This result as well as the fact that the energy barrier (DELTAG(double dagger)) for the benzene ring inversion could not be detected by the VT NMR method indicated that the barrier is much lower than that of trimethylene bridge inversion (DELTAG(double dagger) = 11-12 kcal/mol). The most stable conformer of 1-d4 and 2-d4 is a syn(chair-chair), and the less stable conformer is estimated to be a syn(chair-boat) on the basis of the H-1 NMR data.
• Conformational analysis of 12,12,21,21-tetradeuterio-1,4-dioxa-[4.3.3](1,3,5)Cyclophane
  作者：Katsuya Sako、Takafumi Hirakawa、Naoki Fujimoto、Teruo Shinmyozu、Takahiko Inazu、Hideaki Horimoto

  DOI：10.1016/s0040-4039(00)82324-2

  日期：1988.1