[1RS,2RS,3RS,10SR,11SR,12SR]-3,10-epoxytetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-4,6,8,13-tetraene | 487021-59-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: [1RS,2RS,3RS,10SR,11SR,12SR]-3,10-epoxytetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-4,6,8,13-tetraene
• 英文别名: 3,10-epoxytetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-4,6,8,13-tetraene；(1R,2S,3S,10R,11R,12S)-17-oxapentacyclo[10.2.2.13,10.02,11.04,9]heptadeca-4,6,8,13-tetraene
• CAS: 487021-59-0
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: USDJNWGFKJNHPR-QDMSHXQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  6.0
• 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：

  [1RS,2RS,3RS,10SR,11SR,12SR]-3,10-epoxytetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-4,6,8,13-tetraene 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 9.0h， 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：

  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：

  1,4-二氢-1,4-环氧萘 、 1,3-环己二烯 以 氯仿 为溶剂， 反应 672.0h， 以65%的产率得到[1RS,2RS,3RS,10SR,11SR,12SR]-3,10-epoxytetracyclo[10.2.2.0^2,11.0^4,9]hexadeca-4,6,8,13-tetraene
  参考文献：
  名称：

  1,4-二氢萘-1,4-环氧化物与环己二烯和 7-（甲氧羰基）环庚三烯的环加成反应：加成的选择性

  摘要：

  萘-1,4-环氧化物 (1) 与 7-(甲氧基羰基) 环庚三烯 (2) 和环己二烯 (4) 的环加成反应仅产生类型 3 和 5 的加合物。观察到环加成和溴化反应的选择性，但在后者中也发生了相邻基团的参与。讨论了产物的形成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300569

文献信息

• Cycloaddition Reactions of 1,4-Dihydronaphthalene-1,4-epoxide with Cyclohexadiene and 7-(Methoxycarbonyl)cycloheptatriene: Selectivity in Additions
  作者：Abdullah Menzek、Aliye Altundaş、Ufuk Çoruh、Nihat Akbulut、Ezequiel M. Vázquez López、Tuncer Hökelek、Ahmet Erdönmez

  DOI：10.1002/ejoc.200300569

  日期：2004.3

  Cycloaddition reactions of naphthalene-1,4-epoxide (1) with both 7-(methoxycarbonyl)cycloheptatriene (2) and cyclohexadiene (4) give adducts of type 3 and 5 exclusively. Selectivity was observed for the cycloaddition and bromination reactions, but neighboring group participation also occurrs in the latter. The formation of the products is discussed. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  萘-1,4-环氧化物 (1) 与 7-(甲氧基羰基) 环庚三烯 (2) 和环己二烯 (4) 的环加成反应仅产生类型 3 和 5 的加合物。观察到环加成和溴化反应的选择性，但在后者中也发生了相邻基团的参与。讨论了产物的形成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• 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.