methyl 1,2-seco-2,1α-lactone-1,3-epoxy-3β-hydroxy-11-oxo-12-oleanen-28-oate | 161822-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: methyl 1,2-seco-2,1α-lactone-1,3-epoxy-3β-hydroxy-11-oxo-12-oleanen-28-oate
• 英文别名: 3β-hydroxy-28-methoxy-11,28-dixo-2-oxaolean-12-ene-3,1-carbolactone；methyl (1R,2S,3S,7S,12S,15S,16R,19R,21R)-21-hydroxy-2,9,9,15,16,20,20-heptamethyl-4,22-dioxo-23,24-dioxahexacyclo[19.2.1.02,19.03,16.06,15.07,12]tetracos-5-ene-12-carboxylate
• CAS: 161822-79-3
• 化学式: C₃₁H₄₄O₇
• 分子量: 528.686
• InChiKey: XQZUMXMUAIREIC-KKQNDZAXSA-N

物化性质

• 沸点：
  602.6±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 methyl 1,2-seco-2,1α-lactone-1,3-epoxy-3β-hydroxy-11-oxo-12-oleanen-28-oate 以 乙醚 为溶剂， 反应 10.0h， 以73.7%的产率得到dimethyl 1,3,11-trioxo-1,2-secoolean-12-ene-2,28-dioate
  参考文献：
  名称：

  Zaprutko, L., Polish Journal of Chemistry, 1994, vol. 68, # 9, p. 1753 - 1766

  摘要：

  DOI：
• 作为产物：
  描述：

  齐墩果酸甲酯 在 chromium(VI) oxide 、 硫酸 、 溶剂黄146 作用下， 生成 methyl 1,2-seco-2,1α-lactone-1,3-epoxy-3β-hydroxy-11-oxo-12-oleanen-28-oate
  参考文献：
  名称：

  Triterpenoide. VII. Über die Struktur von neuen 2-oxa- und 1,2-seco-Derivaten des Olenanolsäuremethylesters

  摘要：

  The X-ray crystal structure analysis of 3 beta-hydroxy-28-methoxy-11,28-dioxo-2-oxaolean-12-ene-3,1-carbolactone, (2), and dimethyl 1,3,11-trioxo-1,2-secoolean-12-ene-2,28-dioate, (3), confirms the structure of (2) and (3) previously derived by spectroscopic methods. The hydroxyl group at C(3) in (2) and the side chain at C(5) in (3) are in equatorial positions. In (3), the C(1)=O(4) carbonyl group is antiperiplanar with respect to the C(25) methyl group, the C(3)=O(1) carbonyl group synperiplanar relative to the C(5)-C(6) bond and anticlinal to the C(2)=O(3) carbonyl group. In both compounds, C(28), O(6), O(7) and C(31) in the C(17) ester group are coplanar; the torsion angles C(18)-C(17)-C(28)-O(6) are quite different. The position of the ester group in (2) is stabilized by an intermolecular hydrogen bond. In both compounds, ring C has a slightly distorted sofa conformation; all other rings have deformed chair conformations. Rings D and E are cis-fused.

  DOI：

  10.1107/s010827019400973x

文献信息

• Zaprutko, L., Polish Journal of Chemistry, 1994, vol. 68, # 9, p. 1753 - 1766
  作者：Zaprutko, L.

  DOI：——

  日期：——
• Triterpenoide. VII. Über die Struktur von neuen 2-oxa- und 1,2-seco-Derivaten des Olenanolsäuremethylesters
  作者：A. Gzella、U. Wrzeciono、L. Zaprutko

  DOI：10.1107/s010827019400973x

  日期：1995.5.15

  The X-ray crystal structure analysis of 3 beta-hydroxy-28-methoxy-11,28-dioxo-2-oxaolean-12-ene-3,1-carbolactone, (2), and dimethyl 1,3,11-trioxo-1,2-secoolean-12-ene-2,28-dioate, (3), confirms the structure of (2) and (3) previously derived by spectroscopic methods. The hydroxyl group at C(3) in (2) and the side chain at C(5) in (3) are in equatorial positions. In (3), the C(1)=O(4) carbonyl group is antiperiplanar with respect to the C(25) methyl group, the C(3)=O(1) carbonyl group synperiplanar relative to the C(5)-C(6) bond and anticlinal to the C(2)=O(3) carbonyl group. In both compounds, C(28), O(6), O(7) and C(31) in the C(17) ester group are coplanar; the torsion angles C(18)-C(17)-C(28)-O(6) are quite different. The position of the ester group in (2) is stabilized by an intermolecular hydrogen bond. In both compounds, ring C has a slightly distorted sofa conformation; all other rings have deformed chair conformations. Rings D and E are cis-fused.