(+/-)-dimethyl 3,6b,8,9,9a,9b-hexahydro-7H-cyclopentaacenaphthylene-3,9b-dicarboxylate | 143332-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-dimethyl 3,6b,8,9,9a,9b-hexahydro-7H-cyclopentaacenaphthylene-3,9b-dicarboxylate
• 英文别名: (+/-)-dimethyl 3,6b,8,9,9a,9b-hexahydro-7H-cyclopenta[a]acenaphthylene-3,9b-dicarboxylate；dimethyl (3S,6bR,9aS,9bR)-3,6b,7,8,9,9a-hexahydrocyclopenta[a]acenaphthylene-3,9b-dicarboxylate
• CAS: 143332-06-3
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: UUPWSVSCIZRHPP-MBIOBJJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-萘二甲酸二甲酯 、 环戊烯 以 苯 为溶剂， 以70%的产率得到(+/-)-dimethyl 3,6b,8,9,9a,9b-hexahydro-7H-cyclopentaacenaphthylene-3,9b-dicarboxylate
  参考文献：
  名称：

  A novel 1,8-photoaddition of dimethyl 1,4-naphthalenedicarboxylate to alkenes

  摘要：

  Irradiation of dimethyl 1,4-naphthalenedicarboxylate (1) with various alkenes 2, and 10a-d is found to give novel 1,8-adducts 3, 11a-d, 12a,b,d, and 13b,d. The 1,8-photoaddition proceeds with retention of the stereochemistry of the alkenes in the reactions with trans- and cis-2-butene (5 and 7). Because there is no evidence for a preformed ground-state complex between 1 and the alkenes, the 1,8-addition proceeds from the singlet excited state of 1. Fluorescence of 1 is inefficiently but significantly quenched by alkenes, and an exciplex emission is observed on quenching by 10c. A possible mechanism for the 1,8-photoaddition, involving exciplex formation and an almost synchronous two-bond formation in the exciplex to give a zwitterionic intermediate 15 followed by suprafacial proton transfer, is proposed.

  DOI：

  10.1021/ja00046a009

文献信息

• A novel 1,8-photoaddition of dimethyl 1,4-naphthalenedicarboxylate to alkenes
  作者：Yasuo Kubo、Takeo Inoue、Hidefusa Sakai

  DOI：10.1021/ja00046a009

  日期：1992.9

  Irradiation of dimethyl 1,4-naphthalenedicarboxylate (1) with various alkenes 2, and 10a-d is found to give novel 1,8-adducts 3, 11a-d, 12a,b,d, and 13b,d. The 1,8-photoaddition proceeds with retention of the stereochemistry of the alkenes in the reactions with trans- and cis-2-butene (5 and 7). Because there is no evidence for a preformed ground-state complex between 1 and the alkenes, the 1,8-addition proceeds from the singlet excited state of 1. Fluorescence of 1 is inefficiently but significantly quenched by alkenes, and an exciplex emission is observed on quenching by 10c. A possible mechanism for the 1,8-photoaddition, involving exciplex formation and an almost synchronous two-bond formation in the exciplex to give a zwitterionic intermediate 15 followed by suprafacial proton transfer, is proposed.