18-oxa[2.2.1](1,3,2)cyclophane | 14807-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 18-oxa[2.2.1](1,3,2)cyclophane
• 英文别名: 10,11-dihydro-4,6-ethano-dibenzo[b,f]oxepine；14-oxatetracyclo[10.3.2.05,15.08,13]heptadeca-1(15),2,4,8,10,12-hexaene
• CAS: 14807-37-5
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: IDGAIBKFDUUGOK-UHFFFAOYSA-N

物化性质

• 沸点：
  413.7±40.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  5,13-di-tert-butyl-8,16-dimethoxy-[2.2]metacyclophane 在 三氯化铝 、 Nafion-H 作用下， 以 硝基甲烷 、 苯 为溶剂， 反应 24.0h， 生成 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

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。