1,3-di-tert-butyl-1,4-dihydro-1,4-ethanonaphthalene-9,10-dione | 24478-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,3-di-tert-butyl-1,4-dihydro-1,4-ethanonaphthalene-9,10-dione
• 英文别名: 1,3-Di-tert-butyl-9.10-dioxo-1.4-dihydro-1.4-aethano-naphthalin；(1R,8R)-1,12-ditert-butyltricyclo[6.2.2.02,7]dodeca-2,4,6,11-tetraene-9,10-dione
• CAS: 24478-77-1
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: ZYSHDLCCCGOLPK-MGPUTAFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 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：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-di-tert-butyl-1,4-dihydro-1,4-ethanonaphthalene-9,10-dione 以 四氢呋喃 为溶剂， 反应 1.0h， 以0.085 g的产率得到1,3-Di-t-butylnaphthalin
  参考文献：
  名称：

  Efficient Diels–Alder Reaction of 1,2-Benzoquinones with Arynes and Its Utility in One-Pot Reactions

  摘要：

  A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.

  DOI：

  10.1021/ol302997q
• 作为产物：
  描述：

  3,5-二叔丁基邻苯醌 、 2-(三甲基硅)苯基三氟甲烷磺酸盐 在 potassium fluoride 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到1,3-di-tert-butyl-1,4-dihydro-1,4-ethanonaphthalene-9,10-dione
  参考文献：
  名称：

  Efficient Diels–Alder Reaction of 1,2-Benzoquinones with Arynes and Its Utility in One-Pot Reactions

  摘要：

  A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.

  DOI：

  10.1021/ol302997q

文献信息

• Photochemistry of some benzopyrazinobarrelenes
  作者：Chun-Chen Liao、Pwa-Hwa Yang

  DOI：10.1039/c39910000626

  日期：——

  The photorearrangements of the benzopyrazinobarrelenes 1–4 to give benzopyrazinosemibullvalenes have been studied in order to examine the competing aptitude of benzene and pyrazine intramolecularly.

  为了研究苯和吡嗪在分子内的竞争能力，我们研究了苯并吡嗪桶烯 1-4 的光重排反应，从而得到苯并吡嗪巯基戊烯。
• Ried,W.; Eng,J.T.S., Justus Liebigs Annalen der Chemie, 1969, vol. 727, p. 219 - 221
  作者：Ried,W.、Eng,J.T.S.

  DOI：——

  日期：——
• Efficient Diels–Alder Reaction of 1,2-Benzoquinones with Arynes and Its Utility in One-Pot Reactions
  作者：Trinadh Kaicharla、Sachin Suresh Bhojgude、Akkattu T. Biju

  DOI：10.1021/ol302997q

  日期：2012.12.21

  A new protocol for the efficient Diels-Alder reaction of 1,2-benzoquinones with arynes is reported. The aryne generated by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates undergoes a facile Diels-Alder reaction with 1,2-benzoquinones, affording the dioxobenzobicyclooctadienes in moderate to excellent yields. In addition, this methodology has been applied to the one-pot synthesis of benzoquinoxalinobarrelene and naphthalene derivatives.