endo-2-formyl-3-methylenebicyclo<2.2.1>hept-5-ene | 82431-31-0

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: endo-2-formyl-3-methylenebicyclo<2.2.1>hept-5-ene
• 英文别名: endo(1S*,2R*,4R*)-3-methylenebicyclo[2.2.1]hept-5-enyl-2-carbaldehyde；(1S,2R,4R)-3-methylidenebicyclo[2.2.1]hept-5-ene-2-carbaldehyde
• CAS: 82431-31-0
• 化学式: C₉H₁₀O
• 分子量: 134.178
• InChiKey: FQLOPVIJRLVXPI-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  endo-2-formyl-3-methylenebicyclo<2.2.1>hept-5-ene 以 苯 为溶剂， 反应 14.0h， 以28%的产率得到8-methylene-4-oxatetracyclo<4.2.1.0^2,5.0^3,7>nonane
  参考文献：
  名称：

  Synthesis of the D2d-dinoradamantane derivatives having two coaxially oriented unsaturated centers. 6-Methylene-D2d-dinoradamantan-2-one and D2d-dinoradamantane-2,6-dione

  摘要：

  DOI：

  10.1021/jo00139a017
• 作为产物：
  描述：

  (1S,2R,3S,4R)-3-Chlorocarbonyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 、 双氧水 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 63.0h， 生成 endo-2-formyl-3-methylenebicyclo<2.2.1>hept-5-ene
  参考文献：
  名称：

  Synthesis of the D2d-dinoradamantane derivatives having two coaxially oriented unsaturated centers. 6-Methylene-D2d-dinoradamantan-2-one and D2d-dinoradamantane-2,6-dione

  摘要：

  DOI：

  10.1021/jo00139a017

文献信息

• Transition Metal-Catalyzed [4 + 2 + 2] Cycloadditions of Bicyclo[2.2.1]hepta-2,5-dienes (Norbornadienes) and Bicyclo[2.2.2]octa-2,5-dienes¹
  作者：Yan Chen、Rattana Kiattansakul、Bin Ma、John K. Snyder

  DOI：10.1021/jo010268o

  日期：2001.10.1

  The transition-metal-catalyzed [4 + 2 + 2] cycloadditions of norbornadienes, bicyclo[2.2.2]octa-2,5-diene, and benzobarrelene with 1,3-butadienes proceed in excellent yields using cobalt-based catalytic systems. Two key distinctions between these [4 + 2 + 2] cycloadditions and the corresponding transition-metal-catalyzed [2 + 2 +2] reactions of norbornadiene are the requirement of a bimetal catalytic

  降冰片二烯，双环[2.2.2] octa-2,5-二烯和苯并三氢戊烯与1,3-丁二烯的过渡金属催化[4 + 2 + 2]环加成反应均使用钴基催化体系，收率很高。这些[4 + 2 + 2]环加成反应和降冰片二烯相应的过渡金属催化的[2 + 2 +2]反应之间的两个主要区别是前者具有双膦配体的双金属催化体系和在区域中的唯一区域选择性的要求。 2-取代的降冰片二烯的[4 + 2 + 2]反应生成1-取代的加合物。这些区别可能表明[4 + 2 + 2]和[2 + 2 + 2]反应有两种不同的机制。
• Synthesis and Properties of 2,4,6-Trimethylenetricyclo[3.3.0.03,7]octane (Stellatriene) and Its Alkyl Derivatives. Candidates for a Two-Step Cope Rearrangement
  作者：Rolf Gleiter、Christoph Sigwart

  DOI：10.1021/jo00084a019

  日期：1994.3

  The synthesis of 2,4,6-trimethylenetricyclo[3.3.0.0(3,7)] octane (stellatriene, 9), its hexamethyl derivative 37, and the spirocyclic derivatives 67 and 68, substituted at the carbon atom of the saturated bridge of the tricyclic system, are described. Key steps in the syntheses include an intramolecular Paterno-Buchi reaction leading to tetracyclic oxetanes (e.g., 22b, 39, 47, 59, and 60) as well as the cleavage of the oxetane ring induced by various bases. During the synthesis several dienones were prepared (35, 41, 50, 63, and 64). The trienes and the dienones rearrange to triquinane derivatives at temperatures between 25 and 50 degrees C. The half-lives of the molecules in solution have been determined, which indicate only a moderate effect of the methyl groups on the stability. The rearranged products can best be explained by assuming a stepwise Cope rearrangement via two allylic fragments.
• NAKAZAKI, MASAO;NAEMURA, KOICHIRO;HARADA, HIROSHI;NARUTAKI, HIDEYA, J. ORG. CHEM., 1982, 47, N 18, 3470-3474
  作者：NAKAZAKI, MASAO、NAEMURA, KOICHIRO、HARADA, HIROSHI、NARUTAKI, HIDEYA

  DOI：——

  日期：——
• Gleiter, Rolf; Sigwart, Christoph; Kissler, Bernd, Angewandte Chemie, 1989, vol. 101, # 11, p. 1561 - 1563
  作者：Gleiter, Rolf、Sigwart, Christoph、Kissler, Bernd

  DOI：——

  日期：——