methyl (1R,4R,8R)-8-cyclohexyloxy-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-4-carboxylate | 159951-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl (1R,4R,8R)-8-cyclohexyloxy-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-4-carboxylate
• CAS: 159951-54-9
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: BLRAGTKFDRQRJQ-YWPYICTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (S)-(-)- α-甲基苄胺 、 methyl (1R,4R,8R)-8-cyclohexyloxy-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-4-carboxylate 生成 N-(S)-α-methylbenzyl amide of 1-cyclohexyloxy-2-carbomethoxy-cyclohex-3-en-5-ol-2-carboxylic acid
  参考文献：
  名称：

  Marko, Istvan E.; Evans, Graham R.; Declercq, Jean-Paul, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 5-6, p. 295 - 298

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氧代-2H-吡喃-3-甲酸甲酯 、 环己基乙烯醚 在 (R)-1,1'-Bi-2-naphthol 、 N,N-二异丙基乙胺 、 ytterbium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以90%的产率得到methyl (1R,4R,8R)-8-cyclohexyloxy-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-4-carboxylate
  参考文献：
  名称：

  Remarkable effect of basic ligands in the lanthanide-catalysed enantioselective cycloadditions of 3-carbomethoxy-2-pyrone (3-CMP)

  摘要：

  The key-role of basic ligands in attaining high enantiomeric excess in the lanthanide catalysed asymmetric cycloadditions of 3-CMP is reported, A model, rationalising all our previous observations is discussed. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00876-9

文献信息

• Catalytic, enantioselective, inverse electron-demand diels-alder (IEDDA) reactions of 3-carbomethoxy-2-pyrone (3-CMP)
  作者：István E Markó、Graham R Evans

  DOI：10.1016/s0040-4039(00)77029-8

  日期：1994.4

  Cycloaddition reactions between 5-CMP 1 and various vinyl ethers and vinyl sulphides, catalysed by the Yb(OTf)(3)-Binol complex, afford bicyclic lactones 3 in moderate to excellent enantiomeric excesses.
• Marko, Istvan E.; Evans, Graham R.; Declercq, Jean-Paul, Bulletin des Societes Chimiques Belges, 1994, vol. 103, # 5-6, p. 295 - 298
  作者：Marko, Istvan E.、Evans, Graham R.、Declercq, Jean-Paul、Feneau-Dupont, Janine、Tinant, Bernard

  DOI：——

  日期：——
• Remarkable effect of basic ligands in the lanthanide-catalysed enantioselective cycloadditions of 3-carbomethoxy-2-pyrone (3-CMP)
  作者：István E Markó、Isabelle Chellé-Regnaut、Bernard Leroy、Stuart L. Warriner

  DOI：10.1016/s0040-4039(97)00876-9

  日期：1997.6

  The key-role of basic ligands in attaining high enantiomeric excess in the lanthanide catalysed asymmetric cycloadditions of 3-CMP is reported, A model, rationalising all our previous observations is discussed. (C) 1997 Elsevier Science Ltd.
• Tinant, B.; Feneau-Dupont, J.; Declerq, J. P., Bulletin des Societes Chimiques Belges, 1997, vol. 106, # 3, p. 169 - 170
  作者：Tinant, B.、Feneau-Dupont, J.、Declerq, J. P.、Evans, R. G.、Marko, I. E.

  DOI：——

  日期：——