4-Phenyl-6-methyl-1,5-dihydropentalene | 122902-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Phenyl-6-methyl-1,5-dihydropentalene
• 英文别名: 6-methyl-4-phenyl-1,5-dihydropentalene；4-Methyl-6-phenyl-1,5-dihydropentalen
• CAS: 122902-54-9
• 化学式: C₁₅H₁₄
• 分子量: 194.276
• InChiKey: RGIARUWOSFJFME-UHFFFAOYSA-N

物化性质

• 熔点：
  64-66 °C
• 沸点：
  338.6±12.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-Phenyl-6-methyl-1,5-dihydropentalene 以 二氯甲烷 为溶剂， 反应 26.17h， 生成 anti,endo-1,6-dimethyl-11-phenyl-14-oxa-4,6,8-triazahexacyclo<9.5.1.13,9.02,10.04,8.012,16>octadec-2(10)-ene-5,7,13,15-tetrone
  参考文献：
  名称：

  Generation and interception of isodicyclopentadiene tautomers by diene transmissive Diels-Alder reaction of a 1,5-dihydropentalene with a variety of dienophiles

  摘要：

  The cycloaddition of N-methyl-1,2,4-triazoline-3,5-dione (MTAD), dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA), and p-benzoquinone (BQ) with 6-methyl-4-phenyl-1,5-dihydropentalene (1) afforded the mono- and bis-adducts which depended on the dienophilic strength and reaction conditions (temperature, concentration). Thus, for the highly reactive dienophiles MTAD and DMAD, exclusively the bis-adducts (2, 3) were isolated in high yields as products of diene transmissive Diels-Alder reactions; the corresponding mono-adducts (substituted isodicyclopentadienes) were not detected even as transients. The pi-facial selectivity was high (>95% anti selectivity for 2 and 3) for the second addition step, but it decreased to 75% when high substrate concentrations were used (formation of 25% of the syn product 3b). In the case of the less reactive dienophiles MA or BQ, the corresponding intermediary mono-adducts could be detected by H-1 NMR spectroscopy and their conversion to the more stable isodicyclopentadiene tautomers (e.g. 4a to 4b) monitored directly in the reaction mixture. Both tautomers could be trapped intermolecularly for the MA case by addition of MTAD (5, 7) or another equivalent of MA (6, 8). The intramolecular cycloaddition of the isodicyclopentadiene tautomer derived from BQ and 1, namely the mono-adduct 10b, led to the cage compound 11. The double cycloaddition of dienophiles to 1,5-dihydropentalenes provides an efficient and convenient methodology for the synthesis of complex polycyclic ring skeletons.

  DOI：

  10.1021/jo00040a047
• 作为产物：
  描述：

  1-Phenyl-3-methyl-1,2-dihydropentalene 在 aluminum oxide 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到4-Phenyl-6-methyl-1,5-dihydropentalene
  参考文献：
  名称：

  Griesbeck, Axel G., Chemische Berichte, 1991, vol. 124, # 2, p. 403 - 405

  摘要：

  DOI：

文献信息

• Pyrrolidine-catalyzed reactions between .alpha.,.beta.-unsaturated carbonyl compounds and cyclopentadiene: a convenient approach to 1,2- and 1,5-dihydropentalenes
  作者：Axel G. Griesbeck

  DOI：10.1021/jo00282a004

  日期：1989.10
• Synthesis, Structure, and Properties of Twofold Bridged Sesquinorbornenes
  作者：Axel G. Griesbeck、Thomas Deufel、Georg Hohlneicher、Rupert Rebentisch、Jörg Steinwascher

  DOI：10.1002/(sici)1099-0690(199809)1998:9<1759::aid-ejoc1759>3.0.co;2-i

  日期：1998.9

  The twofold bridged sesquinorbornenes 2 and 6 were prepared using sequential [4 + 2] cycloadditions of benzoquinone with 1,5-dihydropentalenes 1 and 5. These syntheses were improved using dilution conditions or a more reactive substituted benzoquinone. Results from semiempirical and ab initio DFT calculations indicated remarkably high pyramidalization angles (phi = 46-47 degrees) for the central C-C double-bond atoms. The chemical reactivity with triplet and singlet oxygen, dimethyldioxirane and N-methyl-1,2,4-triazoline-3,5-dione supports these structural assignments.
• Griesbeck, Axel G., Chemische Berichte, 1990, vol. 123, p. 549 - 554
  作者：Griesbeck, Axel G.

  DOI：——

  日期：——
• GRIESBECK, AXEL G., J. ORG. CHEM., 54,(1989) N1, C. 4981-4982
  作者：GRIESBECK, AXEL G.

  DOI：——

  日期：——
• Griesbeck, Axel G., Chemische Berichte, 1991, vol. 124, # 2, p. 403 - 405
  作者：Griesbeck, Axel G.

  DOI：——

  日期：——