三环[6.2.1.02.7]十一碳-4,9-二烯-3,6-二酮 | 1200-89-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 三环[6.2.1.02.7]十一碳-4,9-二烯-3,6-二酮
• 英文名称: 1,4,4a,8a-tetrahydro-1,4-methanonaphthalene-5,8-dione
• 英文别名: 1,4-Methano-1,4,4a,8a-tetrahydro-naphthalin-5,8-dion；(2R,7S)-tricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione
• CAS: 1200-89-1；51175-59-8；54353-48-9；100897-81-2
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: FQLRTGXTYFCECH-COMYQFAHSA-N

物化性质

• 熔点：
  77-79 °C(lit.)
• 沸点：
  265.17°C (rough estimate)
• 密度：
  1.0844 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  三环[6.2.1.02.7]十一碳-4,9-二烯-3,6-二酮 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 36.5h， 生成 5,8-bis(4-diphenylphosphoranylbenzyloxy)-1,4-dihydro-1,4-methanonaphthalene
  参考文献：
  名称：

  Polymeric Phosphine Ligand from Ring-Opening Metathesis Polymerization of a Norbornene Derivative. Applications in the Heck, Sonogashira, and Negishi Reactions

  摘要：

  The phosphine-containing polymer 1 is obtained by ruthenium-catalyzed ring-opening metathesis polymerization of the norbornene derivative 2. Polymer 1 is employed as the polymer support in the palladium-catalyzed Heck, Sonogashira, and Negishi reactions, and the corresponding (methoxymethylphenyl)diphenylphosphine (6) ligand is used for comparison. The polymer-supported catalysts retain most of their catalytic activities in these coupling reactions in the recycling processes.

  DOI：

  10.1021/jo035318z
• 作为产物：
  描述：

  环戊二烯 、 对苯醌 以 甲醇 为溶剂， 反应 6.0h， 以95%的产率得到三环[6.2.1.02.7]十一碳-4,9-二烯-3,6-二酮
  参考文献：
  名称：

  Polymeric Phosphine Ligand from Ring-Opening Metathesis Polymerization of a Norbornene Derivative. Applications in the Heck, Sonogashira, and Negishi Reactions

  摘要：

  The phosphine-containing polymer 1 is obtained by ruthenium-catalyzed ring-opening metathesis polymerization of the norbornene derivative 2. Polymer 1 is employed as the polymer support in the palladium-catalyzed Heck, Sonogashira, and Negishi reactions, and the corresponding (methoxymethylphenyl)diphenylphosphine (6) ligand is used for comparison. The polymer-supported catalysts retain most of their catalytic activities in these coupling reactions in the recycling processes.

  DOI：

  10.1021/jo035318z

文献信息

• Structural Manifestations of the Retro Diels−Alder Reaction
  作者：Brett R. Pool、Jonathan M. White

  DOI：10.1021/ol006553w

  日期：2000.11.1

  Examination of selected cyclohexene derivatives which are fixed into the boat conformation reveals structural deviations from "normal" C-C bond distances consistent with the early stages of the retro Diels-Alder reaction.

  选定的固定在船形结构中的环己烯衍生物的检测显示与“正常” CC键距的结构偏差，与逆Diels-Alder反应的早期阶段一致。
• The synthesis of epi-epoxydon utilising the Baylis–Hillman reaction
  作者：Thorsten Genski、Richard J.K. Taylor

  DOI：10.1016/s0040-4039(02)00529-4

  日期：2002.5

  -(+/-)-epi-Epoxydon was synthesised by means of a triethylaluminium/ tri-n-butylphosphine-catalysed Baylis-Hillman reaction between an O-protected epoxidised hydroxyquinol core and paraformaldehyde, constituting the first application of the Baylis-Hillman reaction to a highly functionalised beta-substituted enone. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Polymeric Phosphine Ligand from Ring-Opening Metathesis Polymerization of a Norbornene Derivative. Applications in the Heck, Sonogashira, and Negishi Reactions
  作者：Yun-Chin Yang、Tien-Yau Luh

  DOI：10.1021/jo035318z

  日期：2003.12.1

  The phosphine-containing polymer 1 is obtained by ruthenium-catalyzed ring-opening metathesis polymerization of the norbornene derivative 2. Polymer 1 is employed as the polymer support in the palladium-catalyzed Heck, Sonogashira, and Negishi reactions, and the corresponding (methoxymethylphenyl)diphenylphosphine (6) ligand is used for comparison. The polymer-supported catalysts retain most of their catalytic activities in these coupling reactions in the recycling processes.