dimethyl (3aR,9bS)-3a,9b-dihydrobenzo[g][1]benzofuran-2,3-dicarboxylate | 928620-94-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: dimethyl (3aR,9bS)-3a,9b-dihydrobenzo[g][1]benzofuran-2,3-dicarboxylate
• CAS: 928620-94-4
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: FFFXMVZIUVEUDA-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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,9b-dihydrobenzo[g][1]benzofuran-2,3-dicarboxylate 在 Crabtree's catalyst 氢气 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 1.0h， 以93%的产率得到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
• 作为产物：
  描述：

  1,4-epoxy-1,4-dihydronaphthalene 、 丁炔二酸二甲酯 在 [RhCl((R)-2,2'-bis(diphenylphosphine)-1,1'-binaphthyl)]2 NaB(3,5-bis(trifluoromethyl)phenyl)^F₄ 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以95%的产率得到dimethyl (3aR,9bS)-3a,9b-dihydrobenzo[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

文献信息

• Rhodium-Catalyzed Asymmetric Cyclodimerization of Oxa- and Azabicyclic Alkenes
  作者：Takahiro Nishimura、Takahiro Kawamoto、Keigo Sasaki、Eiji Tsurumaki、Tamio Hayashi

  DOI：10.1021/ja068488c

  日期：2007.2.1

  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).