8,16-dimethoxy[2.2]metacyclophane | 116073-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 8,16-dimethoxy[2.2]metacyclophane
• 英文别名: 15,16-Dimethoxytricyclo[9.3.1.14,8]hexadeca-1(15),4(16),5,7,11,13-hexaene
• CAS: 116073-05-3；132486-38-5
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: XETMVCHPCBNZFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  8,16-dimethoxy[2.2]metacyclophane 在 copper(II) nitrate 作用下， 生成 5-nitro-8,16-dimethoxy<2.2>metacyclophane
  参考文献：
  名称：

  [2.2]Metacyclophanes的重氮偶联

  摘要：

  [2.2]在内部位置带有羟基、甲氧基或甲基的Metacyclophanes(=MCPs)对重氮盐表现出比相应的苯酚、苯甲醚或甲苯更强的反应性。还结合偶氮苯组分的紫外光谱估计了这种反应性。

  DOI：

  10.1246/cl.1992.579
• 作为产物：
  描述：

  2,6-二甲基大茴香醚 在 正丁基锂 、 potassium tert-butylate 、 1,2-二溴乙烷 作用下， 生成 8,16-dimethoxy[2.2]metacyclophane
  参考文献：
  名称：

  Methoxymetacyclophanes from 2,6-dimethylanisole

  摘要：

  [n]Metacyclophanes 2 (n = 8-15), [n.n]metacyclophanes 3 (n = 2,5-10), and [5.5.5]metacyclophane 4 were obtained by reacting dianion 1 from 2,6-dimethylanisole with alpha,omega-dihalides. The favored conformations of these cyclophanes were deduced from their NMR spectra and molecular mechanics calculations. An X-ray study showed dimeric cyclophane 3 (n = 9) to crystallize in essentially the conformation calculated to be of lowest energy. The methoxyl groups move through the large ring rapidly on the NMR time scale when the ring is larger than 18-membered for monomeric cyclophanes 2, 16- or 17-membered for dimeric cyclophanes 3, and in trimeric cyclophane 4 with its 24-membered ring.

  DOI：

  10.1021/jo00005a010

文献信息

• New Synthetic Method of [2.2]Cyclophanes via Diselena[3.3]cyclophanes
  作者：Hiroyuki Higuchi、Keita Tani、Tetsuo Otsubo、Yoshiteru Sakata、Soichi Misumi

  DOI：10.1246/bcsj.60.4027

  日期：1987.11

  Syntheses of cyclic diselenides through diselenolates and the following deselenation reactions by means of three ways were studied. The preparation of the cyclic diselenides in the presence of excess sodium borohydride gave thirty-eight diselenides containing diselena[3.3]cyclophanes and alicyclic diseleno compounds in high yields in addition to two triple-bridged selenacyclophanes. Photodeselenation

  研究了二硒化物合成环状二硒化物以及通过三种途径进行的脱硒反应。在过量硼氢化钠存在下制备环状二硒化物，得到了 38 种二硒化物，其中含有二硒 [3.3] 环芳烃和脂环式二硒化物，以及两个三桥联硒环芳烃。三（二甲氨基）膦中二硒化物的光脱硒以比其他两种方法（即苯-史蒂文斯重排/雷尼镍氢解和热解脱硒）高得多的产率提供了一系列 [2.2] 环烷。650℃。本研究表明，光脱硒方法与其前体二硒化物的合成相结合，远优于传统的脱硫方法。
• Diazo Coupling of [2.2]Metacyclophanes
  作者：Akihiko Tsuge、Tetsuji Moriguchi、Shuntaro Mataka、Masashi Tashiro

  DOI：10.1246/cl.1992.579

  日期：1992.4

  [2.2]Metacyclophanes(=MCPs) which carry hydroxy, methoxy or methyl group at the inner position exhibited a stronger reactivity toward diazonium salts than the corresponding phenol, anisole or toluene, respectively. Such a reactivity was also estimated in connection with the UV spectra of the azo benzene component.

  [2.2]在内部位置带有羟基、甲氧基或甲基的Metacyclophanes(=MCPs)对重氮盐表现出比相应的苯酚、苯甲醚或甲苯更强的反应性。还结合偶氮苯组分的紫外光谱估计了这种反应性。
• 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.
• BATES, ROBERT B.;GANGWAR, SANJEEV;KANE, VINAYAK V.;SUVANNACHUT, KESSARA;T+, J. ORG. CHEM., 56,(1991) N, C. 1696-1699
  作者：BATES, ROBERT B.、GANGWAR, SANJEEV、KANE, VINAYAK V.、SUVANNACHUT, KESSARA、T+

  DOI：——

  日期：——
• HIGUCHI, HIROYUKI;TANI, KEITA;OTSUBO, TETSUO;SAKATA, YOSHITERU;MISUMI, SO+, BULL. CHEM. SOC. JAP., 60,(1987) N 11, 4027-4036
  作者：HIGUCHI, HIROYUKI、TANI, KEITA、OTSUBO, TETSUO、SAKATA, YOSHITERU、MISUMI, SO+

  DOI：——

  日期：——