endo-11-isopropylidene-tricyclo(6.2.1.0)undeca-4,9-dien-3,6-dione | 119615-98-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: endo-11-isopropylidene-tricyclo(6.2.1.0)undeca-4,9-dien-3,6-dione
• 英文别名: (1R,2S,7R,8S)-11-propan-2-ylidenetricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione
• CAS: 119615-98-4
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: BBLUQAHHLKKXHA-LPQAMYBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  endo-11-isopropylidene-tricyclo(6.2.1.0)undeca-4,9-dien-3,6-dione 在 盐酸 、 溴 、 silver nitrate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 Acetic acid (1S,2S,3R,4R)-8-acetoxy-2-bromo-9-isopropylidene-3-methoxy-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl ester
  参考文献：
  名称：

  Singh, Ashok Kumar; Yadav, Sudha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 5, p. 486 - 489

  摘要：

  DOI：
• 作为产物：
  描述：

  exo-(1RS,4SR,4aSR,8aRS)-1,4,4a,8a-tetrahydro-9-isopropylidene-1,4-methanonaphthalene 以 氯仿 为溶剂， 生成 endo-11-isopropylidene-tricyclo(6.2.1.0)undeca-4,9-dien-3,6-dione
  参考文献：
  名称：

  Buttrus, Nabeel H.; Cornforth, Sir John; Hitchcock, Peter B., Journal of the Chemical Society. Perkin transactions I, 1987, p. 851 - 858

  摘要：

  DOI：

文献信息

• Fulvene cycloaddition reactions in water: influence on rate and selectivity
  作者：Axel G Griesbeck

  DOI：10.1016/0040-4039(88)85194-3

  日期：1988.1

  The thermal cycloaddition reaction between dimethylpentafulvene and 1,4-benzoquinone or maleic anhydride was investigated under several solvent and concentration conditions. In aqueous media the reaction rates were highly accelerated and the - ratio for could be controlled from 9:1 to 1:9 depending on the formal concentration in water.

  在几种溶剂和浓缩条件下，研究了二甲基戊烯戊烯与1,4-苯醌或马来酸酐之间的热环加成反应。在水性介质中，反应速率被大大加速，并且取决于水中的形式浓度，β-的比率可以控制在9：1至1：9之间。
• Synthese von 7-Alkyliden-tricyclo[6.3.0.02,6]undeca-4,9-dien-3,11-dionen
  作者：Axel G. Griesbeck

  DOI：10.1002/prac.19923340703

  日期：——

  The cycloaddition reaction of 6-alkyl- as well as 6,6-dialkyl substituted pentafulvenes 1a - f with 1,4-benzoquinone proceeded efficiently and highly endo-stereoselectively when water was used as the solvent. The adducts 2a - f easily underwent intramolecular photocycloaddition when irradiated in acetone or cyclohexane. The resulting trishomocubanediones 3a - f could be transformed into linearly fused tricyclopentanoids 4a - f via flash vacuum thermolysis.
• Unprecedented Microwave Effects on the Cycloaddition of Fulvenes. A New Approach to the Construction of Polycyclic Ring Systems
  作者：Bor-Cherng Hong、Yeong-Jou Shr、Ju-Hsiou Liao

  DOI：10.1021/ol017304q

  日期：2002.2.1

  [GRAPHICS]Novel cycloaddition reactions between fulvenes and various alkenes and alkynes are promoted by the use of microwave irradiation. These processes result in the formation of intriguing polycyclic ring systems such as those found in isobarbatene, alcyopterosin, and enokipodin A. Importantly, these reactions do not occur under conventional thermolytic conditions.
• GRIESBECK, AXEL G., TETRAHEDRON LETT, 29,(1988) N 28, C. 3477-3480
  作者：GRIESBECK, AXEL G.

  DOI：——

  日期：——