(Z)-5,5,10,10-tetramethoxylcarbonyl-1-methoxytetradeca-2-ene-7,12-diyne | 844821-47-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-5,5,10,10-tetramethoxylcarbonyl-1-methoxytetradeca-2-ene-7,12-diyne
• 英文别名: tetramethyl (Z)-1-methoxytetradec-2-en-7,12-diyne-4,4,9,9-tetracarboxylate
• CAS: 844821-47-2
• 化学式: C₂₃H₃₀O₉
• 分子量: 450.486
• InChiKey: FVLRKCATWWLGFY-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  苯硼酸 、 (Z)-5,5,10,10-tetramethoxylcarbonyl-1-methoxytetradeca-2-ene-7,12-diyne 在 [Rh(OH)(cod)]2 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 以53%的产率得到(Z)-1,1-dimethoxylcarbonyl-3-[3,3-dimethoxylcarbonyl-5-((Z)-1-phenylethylidene)cyclopentylidene]-4-vinylcyclopentane
  参考文献：
  名称：

  Rhodium-Catalyzed Cyclization of 1,6-Enynes Triggered by Addition of Arylboronic Acids

  摘要：

  1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by beta-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.

  DOI：

  10.1021/ja0435079
• 作为产物：
  描述：

  dimethyl propargylmalonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (Z)-5,5,10,10-tetramethoxylcarbonyl-1-methoxytetradeca-2-ene-7,12-diyne
  参考文献：
  名称：

  Rhodium-Catalyzed Cyclization of 1,6-Enynes Triggered by Addition of Arylboronic Acids

  摘要：

  1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by beta-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.

  DOI：

  10.1021/ja0435079

文献信息

• Rhodium-Catalyzed Cyclization of 1,6-Enynes Triggered by Addition of Arylboronic Acids
  作者：Tomoya Miura、Masahiko Shimada、Masahiro Murakami

  DOI：10.1021/ja0435079

  日期：2005.2.1

  1,6-Enynes reacted with arylboronic acids in the presence of a catalytic amount of a rhodium(I) complex under mild conditions to give (Z)-1-(1-arylethylidene)-2-vinylcyclopentanes. The regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond triggered the cyclization process. Intramolecular carborhodation onto the pendent alkene in a 5-exo mode furnished a five-membered ring. Finally, the rhodium(I) methoxide generated by beta-methoxy elimination reacted with the arylboronic acid to promote the next catalytic cycle.