2,5-etheno<4.3.2>propella-3,8,10-trien-7-one | 131236-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-etheno<4.3.2>propella-3,8,10-trien-7-one
• 英文别名: tetracyclo[4.3.2.22,5.01,6]trideca-3,8,10,12-tetraen-7-one
• CAS: 131236-19-6
• 化学式: C₁₃H₁₀O
• 分子量: 182.222
• InChiKey: VBVHDQDSEALALV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,5-etheno<4.3.2>propella-3,8,10-trien-7-one 以 甲醇 为溶剂， 反应 0.33h， 生成 hexacyclo[6.5.0.01,11.02,7.05,11.06,9]trideca-3,12-dien-10-one
  参考文献：
  名称：

  .pi.-Facial selectivity in Diels-Alder reactions of [4.3.2]propella-2,4,8,10-tetraen-7-one and its derivatives. Synthesis of 2,5-etheno[4.3.2]propella-3,8,10-trien-7-ones

  摘要：

  The Diels-Alder additions of dimethyl acetylenedicarboxylate, methyl propiolate, and maleic anhydride to [4.3.2]propella-2,4,8,10-tetraen-7-one (1), and its 8,9- and 10,11-dihydro derivatives, 2 and 3, and [4.3.2]propella-2,4,7,10-tetraene (4) occur steroselectively at the face of cyclohexadiene ring syn to five-membered ring. The-pi-facial selectivity of the additions is rationalized in terms of difference in dihedral angles between the cyclohexadiene and two flanking rings. Treatment of the adduct of maleic anhydride to 1 with Ni(PPh3)2(CO)2 gives 2,5-etheno[4.3.2]propella-3,8,10-trien-7-one (5a). The electronic absorption spectrum of 5a exhibits characteristic longer wave absorptions compared with the corresponding partly saturated derivatives, suggesting the existence of longicyclic interaction among its four-pi-bonds. Irradiation of 5a results in transannular [2 + 2] cycloaddition rather than cleavage into antiaromatic bicyclo[3.2.0]heptatrienone and benzene.

  DOI：

  10.1021/jo00003a020
• 作为产物：
  描述：

  <4.3.2>Propella-2,4,8,10-tetraen-7-one 在 双三苯基膦二羰基镍 作用下， 以 二乙二醇二甲醚 、 苯 为溶剂， 反应 5.67h， 生成 2,5-etheno<4.3.2>propella-3,8,10-trien-7-one
  参考文献：
  名称：

  .pi.-Facial selectivity in Diels-Alder reactions of [4.3.2]propella-2,4,8,10-tetraen-7-one and its derivatives. Synthesis of 2,5-etheno[4.3.2]propella-3,8,10-trien-7-ones

  摘要：

  The Diels-Alder additions of dimethyl acetylenedicarboxylate, methyl propiolate, and maleic anhydride to [4.3.2]propella-2,4,8,10-tetraen-7-one (1), and its 8,9- and 10,11-dihydro derivatives, 2 and 3, and [4.3.2]propella-2,4,7,10-tetraene (4) occur steroselectively at the face of cyclohexadiene ring syn to five-membered ring. The-pi-facial selectivity of the additions is rationalized in terms of difference in dihedral angles between the cyclohexadiene and two flanking rings. Treatment of the adduct of maleic anhydride to 1 with Ni(PPh3)2(CO)2 gives 2,5-etheno[4.3.2]propella-3,8,10-trien-7-one (5a). The electronic absorption spectrum of 5a exhibits characteristic longer wave absorptions compared with the corresponding partly saturated derivatives, suggesting the existence of longicyclic interaction among its four-pi-bonds. Irradiation of 5a results in transannular [2 + 2] cycloaddition rather than cleavage into antiaromatic bicyclo[3.2.0]heptatrienone and benzene.

  DOI：

  10.1021/jo00003a020

文献信息

• TSUJI, TAKASHI;OHKITA, MASAKAZU;NISHIDA, SHINYA, J. ORG. CHEM., 56,(1991) N, C. 997-1003
  作者：TSUJI, TAKASHI、OHKITA, MASAKAZU、NISHIDA, SHINYA

  DOI：——

  日期：——
• .pi.-Facial selectivity in Diels-Alder reactions of [4.3.2]propella-2,4,8,10-tetraen-7-one and its derivatives. Synthesis of 2,5-etheno[4.3.2]propella-3,8,10-trien-7-ones
  作者：Takashi Tsuji、Masakazu Ohkita、Shinya Nishida

  DOI：10.1021/jo00003a020

  日期：1991.2

  The Diels-Alder additions of dimethyl acetylenedicarboxylate, methyl propiolate, and maleic anhydride to [4.3.2]propella-2,4,8,10-tetraen-7-one (1), and its 8,9- and 10,11-dihydro derivatives, 2 and 3, and [4.3.2]propella-2,4,7,10-tetraene (4) occur steroselectively at the face of cyclohexadiene ring syn to five-membered ring. The-pi-facial selectivity of the additions is rationalized in terms of difference in dihedral angles between the cyclohexadiene and two flanking rings. Treatment of the adduct of maleic anhydride to 1 with Ni(PPh3)2(CO)2 gives 2,5-etheno[4.3.2]propella-3,8,10-trien-7-one (5a). The electronic absorption spectrum of 5a exhibits characteristic longer wave absorptions compared with the corresponding partly saturated derivatives, suggesting the existence of longicyclic interaction among its four-pi-bonds. Irradiation of 5a results in transannular [2 + 2] cycloaddition rather than cleavage into antiaromatic bicyclo[3.2.0]heptatrienone and benzene.