methyl 8-phenyl-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-9-carboxylate | 264912-67-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 8-phenyl-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-9-carboxylate
• CAS: 264912-67-6
• 化学式: C₁₈H₁₄O₃
• 分子量: 278.307
• InChiKey: KVELSNWQWCBAKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-苄基-1-丁氧基-N-[(三甲基硅烷基)甲基]甲胺 、 methyl 8-phenyl-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-9-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 4,9-epoxy-9-phenyl-2-phenylmethyl-1,3,4,9,10,11-hexahydrobenzo[f]isoindole-10-carboxylate
  参考文献：
  名称：

  A Diastereoselective Switch in the Access to Isobenzofuran-Derived α-Selenoesters

  摘要：

  [GRAPHICS]The cycloaddition of 1-phenylisobenzofuran (PIBF) with methyl acrylate yields, in a moderate endo/exo ratio, the expected era-bridged adduct, which can be deprotonated and condensed on diphenyl diselenide to provide, in a stereoconvergent step, the "endo" alpha-selenoester. Its "exo" epimer is obtained by reacting PIBF and methyl alpha-phenylselenoacrylate. These adducts can be oxidized to give a common unsaturated bridged ester that can react with an imminium ylide to provide the expected pyrrolidine stereoselectively.

  DOI：

  10.1021/ol005560h
• 作为产物：
  描述：

  3-methyloxycarbonyl-3-phenylselenyl-1,4-epoxy-4-phenyl-1,2,3,4-tetrahydronaphthalene 在 双氧水 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 8-phenyl-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-9-carboxylate
  参考文献：
  名称：

  A Diastereoselective Switch in the Access to Isobenzofuran-Derived α-Selenoesters

  摘要：

  [GRAPHICS]The cycloaddition of 1-phenylisobenzofuran (PIBF) with methyl acrylate yields, in a moderate endo/exo ratio, the expected era-bridged adduct, which can be deprotonated and condensed on diphenyl diselenide to provide, in a stereoconvergent step, the "endo" alpha-selenoester. Its "exo" epimer is obtained by reacting PIBF and methyl alpha-phenylselenoacrylate. These adducts can be oxidized to give a common unsaturated bridged ester that can react with an imminium ylide to provide the expected pyrrolidine stereoselectively.

  DOI：

  10.1021/ol005560h