1,4-diphenyl-14-bromo-8,12b-dihydro-8,12b-ethanobenz[a]aceanthrylene-endo-13,14-dicarboxylic acid anhydride

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 1,4-diphenyl-14-bromo-8,12b-dihydro-8,12b-ethanobenz[a]aceanthrylene-endo-13,14-dicarboxylic acid anhydride
• 英文别名: (1S,13S,20R,24S)-24-bromo-3,6-diphenyl-22-oxaheptacyclo[11.6.5.11,8.02,7.014,19.020,24.012,25]pentacosa-2,4,6,8(25),9,11,14,16,18-nonaene-21,23-dione
• 化学式: C₃₆H₂₁BrO₃
• 分子量: 581.465
• InChiKey: SFQVLLIGRBKBLO-SXKGIHEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴代马来酸酐 、 1,4-diphenyl-benz[a]aceanthrylene 以 甲苯 为溶剂， 反应 10.0h， 以56%的产率得到1,4-diphenyl-14-bromo-8,12b-dihydro-8,12b-ethanobenz[a]aceanthrylene-endo-13,14-dicarboxylic acid anhydride
  参考文献：
  名称：

  Stereochemical π-Facial Selectivity of the Diels−Alder Reaction of Benz[a]aceanthrylene and 1,4-Diphenylbenz[a]aceanthrylene

  摘要：

  The Diels-Alder (D-A) reaction of the twisted hydrocarbon 1,4-diphenylbenz[a]aceanthrylene (4) with dienophiles maleic anhydride, bromomaleic anhydride, and N-phenylmaleimide and with benzyne is reported. The stereochemistry of the products derived from the D-A reaction of 4 is compared with the products derived from reaction of planar benz[a]aceanthrylene (5) with maleic anhydride as a model. The endo regiochemical pi-facial selectivity of 4 appears to be the result of the steric effect of a phenyl substituent as the transition state is reached. Compound 5 produces both endo and exo D-A adducts when treated with maleic anhydride, X-ray crystallographic analysis verifies the topology of the bromomaleic anhydride adduct of 4 and the maleic anhydride adduct of 5.

  DOI：

  10.1021/jo971610t

文献信息

• Stereochemical π-Facial Selectivity of the Diels−Alder Reaction of Benz[<i>a</i>]aceanthrylene and 1,4-Diphenylbenz[<i>a</i>]aceanthrylene
  作者：Benjamin F. Plummer、Saadia Faiz、Ted Wiederhold、Marilyn Wooten、Joseph K. Agyin、Kurt L. Krause、Mitchell D. Miller、William H. Watson

  DOI：10.1021/jo971610t

  日期：1997.12.1

  The Diels-Alder (D-A) reaction of the twisted hydrocarbon 1,4-diphenylbenz[a]aceanthrylene (4) with dienophiles maleic anhydride, bromomaleic anhydride, and N-phenylmaleimide and with benzyne is reported. The stereochemistry of the products derived from the D-A reaction of 4 is compared with the products derived from reaction of planar benz[a]aceanthrylene (5) with maleic anhydride as a model. The endo regiochemical pi-facial selectivity of 4 appears to be the result of the steric effect of a phenyl substituent as the transition state is reached. Compound 5 produces both endo and exo D-A adducts when treated with maleic anhydride, X-ray crystallographic analysis verifies the topology of the bromomaleic anhydride adduct of 4 and the maleic anhydride adduct of 5.