tetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-2,4,6,8,10-pentaene | 55178-88-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: tetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-2,4,6,8,10-pentaene
• 英文别名: 2,3-Naphtobarrelan；1,2,3,4-Tetrahydro-1,4-ethanoanthracene；tetracyclo[10.2.2.02,11.04,9]hexadeca-2,4,6,8,10-pentaene
• CAS: 55178-88-6
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: GWIMEYSSSXDNBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  tetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-2,4,6,8,10-pentaene 在 palladium on activated charcoal sodium 、 叔丁醇 、 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 168000.0h， 以75 mg的产率得到tetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-2(11),3,9-triene
  参考文献：
  名称：

  Reactions of 3,10-epoxycyclo[10.2.2.02,11.04,9]hexadeca-4,6,8,13-tetraene: a new intramolecular 1,5-oxygen migration

  摘要：

  Bromination of 3,10-epoxycyclo[10.2.2.0(2,11).0(4.9)]hexadeca-4,6,8,13-tetraene gave 13-bromo-11-oxapentacyclo[8.7.0.0(2,4).0(12,17)]-heptadeca-4,6,8-triene-3-ol, 12-bromo-1,2,3,4-tetrahydro-1,4-ethano-antracen-ll-ol, 13-hydroxy-3,14-dibromotetracyclo[10.2.2.0(2,11).0(4,9)]hexadeca-2,4,6,8,10-pentaene, and 13-hydroxy-3,10,14-tribromotetracyclo[10.2.2.0(2,11).0(4,9)]hexadeca-2,4,6,8,10-pentaene by cleavage of the carbon-oxygen bonds and intramolecular 1,5-migration of the oxygen atom of 1,4-epoxide. Reactions of epoxide 14,18-dioxahexacyclo[10.3.2.1(3.10).0(2,11).0(4,9).0(13,15)] octadeca-4,6,8-triene obtained from 3,10-epoxycyclo[10.2.2.0(2,11).0(4,9)]hexadeca-4,6,8,13-tetraene gave also similar products, in acidic media. Compound 3,10-epoxycyclo[10.2.2.0(2,11).0(4,9)]hexadeca-4,6,8,13-tetraene was converted into tetracyclo[10.2.2.0(2,11).0(4.9)] hexadeca-2(11),3,9-triene in two ways. The reactions, especially intramolecular oxygen migration, are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.012
• 作为产物：
  描述：

  1,4,4a,9,9a,10-Hexahydro-1,4-ethanoanthracene-9,10-diol 在 palladium on activated charcoal 吡啶 、 氢气 、 三氯氧磷 作用下， 以 乙酸乙酯 为溶剂， 生成 tetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-2,4,6,8,10-pentaene
  参考文献：
  名称：

  4b，5、12、12a-四氢-5、12-乙基-13 H-茚并[2,3- b ]蒽，4b，5、10、10a-四氢-5,10 - ethano -11 H的合成-茚并[2,3- b ]萘的和-1,2,3，9α-二六氢-1,4-（围绝经期naphthaleno）-fluorenes

  摘要：

  合成内切-和外切-13-氧4B，图5，图12，图12a-四氢5,12-ethanoindeno [2,3- b ]蒽（23 ;方案1和2），外切-和内切-11 -oxo-4b，5、10、10a-四氢-5、10-乙基茚并[2,3- b ]萘（31 ;方案3），1,2,3,4,4a，9a-hexahydro-1 ，4-（围naphthaleno）芴-9-酮（36 ;方案4），以及立体异构酮对相应的烃23和36，进行说明。

  DOI：

  10.1002/hlca.19750580208

文献信息

• Hyperfine coupling patterns in the 2,3-naphthobarrelene and 2,3-naphthobarrelane radical anions
  作者：John R. Dodd、George V. Sanzero

  DOI：10.1021/ja00850a023

  日期：1975.8
• The Synthesis of 4b, 5, 12, 12a-Tetrahydro-5, 12-ethano-13H-indeno[2,3-b]anthracenes, 4b, 5, 10, 10a - tetrahydro-5,10-ethano-11H-indeno[2,3-b]naphtalenes and 1,2,3,4,4a, 9a-Hexahydro-1,4-(peri-naphthaleno)-fluorenes
  作者：Walter Amrein、Kurt Schaffner

  DOI：10.1002/hlca.19750580208

  日期：——

  The synthesis of endo- and exo-13-oxo-4b, 5, 12, 12a-tetrahydro-5, 12-ethanoindeno[2,3-b]anthracene (23; Schemes 1 and 2), exo- and endo-11-oxo-4b, 5, 10, 10a-tetrahydro-5, 10-ethano-indeno[2,3-b]naphthalene (31; Scheme 3), 1,2,3,4,4a,9a-hexahydro−1,4-(peri-naphthaleno)-fluoren-9-one (36; Scheme 4), and the corresponding hydrocarbons of the stereoisomeric ketone pairs 23 and 36, is described.

  合成内切-和外切-13-氧4B，图5，图12，图12a-四氢5,12-ethanoindeno [2,3- b ]蒽（23 ;方案1和2），外切-和内切-11 -oxo-4b，5、10、10a-四氢-5、10-乙基茚并[2,3- b ]萘（31 ;方案3），1,2,3,4,4a，9a-hexahydro-1 ，4-（围naphthaleno）芴-9-酮（36 ;方案4），以及立体异构酮对相应的烃23和36，进行说明。
• Reactions of 3,10-epoxycyclo[10.2.2.02,11.04,9]hexadeca-4,6,8,13-tetraene: a new intramolecular 1,5-oxygen migration
  作者：Abdullah Menzek、Aliye Altundaş

  DOI：10.1016/j.tet.2006.10.012

  日期：2006.12

  Bromination of 3,10-epoxycyclo[10.2.2.0(2,11).0(4.9)]hexadeca-4,6,8,13-tetraene gave 13-bromo-11-oxapentacyclo[8.7.0.0(2,4).0(12,17)]-heptadeca-4,6,8-triene-3-ol, 12-bromo-1,2,3,4-tetrahydro-1,4-ethano-antracen-ll-ol, 13-hydroxy-3,14-dibromotetracyclo[10.2.2.0(2,11).0(4,9)]hexadeca-2,4,6,8,10-pentaene, and 13-hydroxy-3,10,14-tribromotetracyclo[10.2.2.0(2,11).0(4,9)]hexadeca-2,4,6,8,10-pentaene by cleavage of the carbon-oxygen bonds and intramolecular 1,5-migration of the oxygen atom of 1,4-epoxide. Reactions of epoxide 14,18-dioxahexacyclo[10.3.2.1(3.10).0(2,11).0(4,9).0(13,15)] octadeca-4,6,8-triene obtained from 3,10-epoxycyclo[10.2.2.0(2,11).0(4,9)]hexadeca-4,6,8,13-tetraene gave also similar products, in acidic media. Compound 3,10-epoxycyclo[10.2.2.0(2,11).0(4,9)]hexadeca-4,6,8,13-tetraene was converted into tetracyclo[10.2.2.0(2,11).0(4.9)] hexadeca-2(11),3,9-triene in two ways. The reactions, especially intramolecular oxygen migration, are discussed. (c) 2006 Elsevier Ltd. All rights reserved.