14β,20-epoxydihydroquinopimaric acid methyl ester | 13447-14-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 14β,20-epoxydihydroquinopimaric acid methyl ester
• 英文别名: methyl (1S,3S,5S,9R,10R,11R,13R,14R,18R,19R)-14,18-dimethyl-8-oxo-3-propan-2-yl-4-oxahexacyclo[11.8.0.01,9.03,11.05,10.014,19]henicosane-18-carboxylate
• CAS: 13447-14-8
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: YHAJHXZFOPDKPM-FSWJIBDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  14β,20-epoxydihydroquinopimaric acid methyl ester 在 溴 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以74%的产率得到methyl (16S)-16-bromo-20-isopropyl-5,9-dimethyl-17-oxo-14-oxahexacyclo[10.6.2(1,10).0(4,9).0(13,18)]-heneicosane-5-carboxylate
  参考文献：
  名称：

  Regioselective bromination of quinopimaric acid derivatives

  摘要：

  Regioselective bromination of 14 beta-hydroxydihydroquinopimaric acid methyl ester in acetic acid and methanol gave the corresponding 16S-bromo-, 19R-bromo-, and 16S,19R-dibromo-14 beta,20-epoxy derivatives whose structure was determined by X-ray analysis and NMR spectroscopy. The reactions of 16S-bromo ketones with thiourea afforded 2,1,3-thiadiazoles fused to diterpene fragment.

  DOI：

  10.1134/s107042801008004x
• 作为产物：
  描述：

  1β-hydroxyquinopimarate 在 盐酸 、 溶剂黄146 作用下， 反应 5.0h， 以18%的产率得到methyl (3aS,3a1R,6R,6aR,7aR,7bR,11R,11aR,13aS,13bR)-5,5,7b,11-tetramethyl-1-oxooctadecahydro-2H-6,13a-methanophenanthro[3,2,1-de]chromene-11-carboxylate
  参考文献：
  名称：

  Molecular structure of methyl-10,14,19,19-tetramethyl-4-oxo-20-oxahexacyclo [15.3.1.16.18.06.15.09.14017.21]docosane-10-carboxylate

  摘要：

  合成了 10,14,19,19-四甲基-4-氧代-20-氧杂六环[15.3.1.16.18.06.15.09.14017.21]二十二烷-10-羧酸甲酯 III，并确定了其分子结构。化合物 III C27H40O4 在单斜晶系中结晶，晶胞参数如下：a = 12.8081(11) Å，b = 7.0384(6) Å，c = 12.8904(12) Å，β = 105.828(2)o，P21 空间群，Z = 2，d = 1.273 mg/m3。

  DOI：

  10.1007/s10947-010-0059-2

文献信息

• Regioselective bromination of quinopimaric acid derivatives
  作者：I. E. Smirnova、O. B. Kazakova、E. V. Tret’yakova、L. V. Spirikhin、I. V. Glukhov、Yu. V. Nelyubina

  DOI：10.1134/s107042801008004x

  日期：2010.8

  Regioselective bromination of 14 beta-hydroxydihydroquinopimaric acid methyl ester in acetic acid and methanol gave the corresponding 16S-bromo-, 19R-bromo-, and 16S,19R-dibromo-14 beta,20-epoxy derivatives whose structure was determined by X-ray analysis and NMR spectroscopy. The reactions of 16S-bromo ketones with thiourea afforded 2,1,3-thiadiazoles fused to diterpene fragment.
• Molecular structure of methyl-10,14,19,19-tetramethyl-4-oxo-20-oxahexacyclo [15.3.1.16.18.06.15.09.14017.21]docosane-10-carboxylate
  作者：I. E. Smirnova、E. V. Tretyakova、O. B. Kazakova

  DOI：10.1007/s10947-010-0059-2

  日期：2010.4

  The synthesis of methyl-10,14,19,19-tetramethyl-4-oxo-20-oxahexacyclo[15.3.1.16.18.06.15.09.14017.21] docosane-10-carboxylate III is performed and its molecular structure is determined. Compound III C27H40O4 crystallizes in the monoclinic system with the cell parameters as follows: a = 12.8081(11) Å, b = 7.0384(6) Å, c = 12.8904(12) Å, β = 105.828(2)o, P21 space group, Z = 2, d = 1.273 mg/m3.

  合成了 10,14,19,19-四甲基-4-氧代-20-氧杂六环[15.3.1.16.18.06.15.09.14017.21]二十二烷-10-羧酸甲酯 III，并确定了其分子结构。化合物 III C27H40O4 在单斜晶系中结晶，晶胞参数如下：a = 12.8081(11) Å，b = 7.0384(6) Å，c = 12.8904(12) Å，β = 105.828(2)o，P21 空间群，Z = 2，d = 1.273 mg/m3。