5,13-di-tert-butyl-17-oxa[2.2.1](1,3,2)cyclophane | 197577-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噁庚英
• 英文名称: 5,13-di-tert-butyl-17-oxa[2.2.1](1,3,2)cyclophane
• 英文别名: 5,13-di-tert-butyl-8,16-epoxy[2.2]metacyclophane；3,10-Ditert-butyl-14-oxatetracyclo[10.3.2.05,15.08,13]heptadeca-1,3,5(15),8(13),9,11-hexaene
• CAS: 197577-56-3
• 化学式: C₂₄H₃₀O
• 分子量: 334.502
• InChiKey: DKRGKOAGEURHFS-UHFFFAOYSA-N

物化性质

• 沸点：
  449.3±45.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,13-di-tert-butyl-17-oxa[2.2.1](1,3,2)cyclophane 在 三氯化铝 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 24.0h， 以75%的产率得到18-oxa[2.2.1](1,3,2)cyclophane
  参考文献：
  名称：

  Medium-Sized Cyclophanes. 43.¹ First Evidence for anti−syn-Ring Inversion under the Nitration of 5,13-Di-tert-butyl-8,16-dimethoxy[2.2]metacyclophane

  摘要：

  Nitration of 5,13-di-tert-butyl-8,16-dimethoxy[2.2]MC (metacyclophane = MCP) (1) with various nitrating reagents led to ipso-nitration at the tert-butyl group to give 5-tert-butyl-8,16-dimethoxy-13-nitro[2.2]MCP (2), as well as the corresponding 8,16-epoxy[2.2]MCP (4) arising from intramolecular condensation reaction via anti-syn-ring inversion of the nitration intermediate. This novel intramolecular condensation reaction to afford 8,16-epoxy[2.2]MCP (4) was also observed in the presence of Nafion-H under chlorobenzene reflux. The mechanism of the ipso-nitration as well as the present novel intramolecular condensation reaction is also discussed.

  DOI：

  10.1021/jo970192p
• 作为产物：
  描述：

  5,13-di-tert-butyl-8,16-dimethoxy-[2.2]metacyclophane 在 Nafion-H 作用下， 以 氯苯 为溶剂， 反应 12.0h， 以34%的产率得到5,13-di-tert-butyl-17-oxa[2.2.1](1,3,2)cyclophane
  参考文献：
  名称：

  Medium-Sized Cyclophanes. 43.¹ First Evidence for anti−syn-Ring Inversion under the Nitration of 5,13-Di-tert-butyl-8,16-dimethoxy[2.2]metacyclophane

  摘要：

  Nitration of 5,13-di-tert-butyl-8,16-dimethoxy[2.2]MC (metacyclophane = MCP) (1) with various nitrating reagents led to ipso-nitration at the tert-butyl group to give 5-tert-butyl-8,16-dimethoxy-13-nitro[2.2]MCP (2), as well as the corresponding 8,16-epoxy[2.2]MCP (4) arising from intramolecular condensation reaction via anti-syn-ring inversion of the nitration intermediate. This novel intramolecular condensation reaction to afford 8,16-epoxy[2.2]MCP (4) was also observed in the presence of Nafion-H under chlorobenzene reflux. The mechanism of the ipso-nitration as well as the present novel intramolecular condensation reaction is also discussed.

  DOI：

  10.1021/jo970192p

文献信息

• Pyrolysis of Dimethoxy[<i>n</i>.2]Metacyclophanes: An Intramolecular Condensation Reaction to Give Oxa[<i>n</i>.2.1](1,3,2)Cyclophanes
  作者：Jung-Hee Do、Yuta Yamada、Bigyan Sharma、Takehiko Yamato

  DOI：10.3184/174751912x13296759770106

  日期：2012.3

  1](1,3,2)cyclophane in 35% yield arising from intramolecular condensation reaction of syn-8,16-dimethoxy[2.2]metacyclophane; similar results were also obtained in the pyrolysis of the higher anti- and syn-dimethoxy[3.2] metacyclophane to afford the corresponding 18-oxa[3.2.1](1,3,2)cyclophane. The mechanism of this novel intramolecular condensation reaction is discussed.

  反 8,16-二甲氧基[2.2] 间环烷在 500°C 下热解得到 17-氧杂[2.2.1](1,3,2)环烷，产率 35%二甲氧基[2.2]间环芳烷；在较高的反和顺二甲氧基[3.2]元环烷的热解中也获得了类似的结果，以提供相应的18-氧杂[3.2.1](1,3,2)环烷。讨论了这种新型分子内缩合反应的机理。
• Medium-Sized Cyclophanes. 43.¹ First Evidence for <i>anti</i>−<i>syn</i>-Ring Inversion under the Nitration of 5,13-Di-<i>tert</i>-butyl-8,16-dimethoxy[2.2]metacyclophane
  作者：Takehiko Yamato、Hideo Kamimura、Tsuyoshi Furukawa

  DOI：10.1021/jo970192p

  日期：1997.10.1

  Nitration of 5,13-di-tert-butyl-8,16-dimethoxy[2.2]MC (metacyclophane = MCP) (1) with various nitrating reagents led to ipso-nitration at the tert-butyl group to give 5-tert-butyl-8,16-dimethoxy-13-nitro[2.2]MCP (2), as well as the corresponding 8,16-epoxy[2.2]MCP (4) arising from intramolecular condensation reaction via anti-syn-ring inversion of the nitration intermediate. This novel intramolecular condensation reaction to afford 8,16-epoxy[2.2]MCP (4) was also observed in the presence of Nafion-H under chlorobenzene reflux. The mechanism of the ipso-nitration as well as the present novel intramolecular condensation reaction is also discussed.