dimethyl (3aR,9bS)-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,3-dicarboxylate | 928621-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: dimethyl (3aR,9bS)-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,3-dicarboxylate
• CAS: 928621-03-8
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: BGYWUDCVVJFZDW-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (3aR,9bS)-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,3-dicarboxylate 、 尿素 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以69%的产率得到(5Z)-5-[(3aR,9bS)-2-oxo-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-3-ylidene]imidazolidine-2,4-dione
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Cyclodimerization of Oxa- and Azabicyclic Alkenes

  摘要：

  Asymmetric homo-cyclodimerization of oxabicyclic alkenes proceeded with high efficiency in the presence of a cationic rhodium/(R)-binap catalyst to give high yields of chiral tetrahydrofurans of up to 99% ee. The cationic rhodium complex also catalyzed the asymmetric cross-cyclodimerization between oxabicyclic alkenes and dimethyl 2-butynedioate, which gave dihydrofurans as [3+2] cycloadducts with high enantioselectivity (99% ee).

  DOI：

  10.1021/ja068488c
• 作为产物：
  描述：

  丁炔二酸二甲酯 在 Crabtree's catalyst 、 [RhCl((R)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl)]2 NaB(3,5-bis(trifluoromethyl)phenyl)^F₄ 、 氢气 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 dimethyl (3aR,9bS)-3a,4,5,9b-tetrahydrobenzo[g][1]benzofuran-2,3-dicarboxylate
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Cyclodimerization of Oxa- and Azabicyclic Alkenes

  摘要：

  Asymmetric homo-cyclodimerization of oxabicyclic alkenes proceeded with high efficiency in the presence of a cationic rhodium/(R)-binap catalyst to give high yields of chiral tetrahydrofurans of up to 99% ee. The cationic rhodium complex also catalyzed the asymmetric cross-cyclodimerization between oxabicyclic alkenes and dimethyl 2-butynedioate, which gave dihydrofurans as [3+2] cycloadducts with high enantioselectivity (99% ee).

  DOI：

  10.1021/ja068488c