3β-hydroxy-11-oxo-18α-oleanen-(12)-oic acid-(28)-methyl ester | 112572-45-9

• 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: 3β-hydroxy-11-oxo-18α-oleanen-(12)-oic acid-(28)-methyl ester
• 英文别名: 3β-Hydroxy-11-oxo-18α-oleanen-(12)-saeure-(28)-methylester；methyl (4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-4a-carboxylate
• CAS: 112572-45-9
• 化学式: C₃₁H₄₈O₄
• 分子量: 484.72
• InChiKey: WWQDFVOIJWUDSM-WHOKMKORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-11-oxo-18α-oleanen-(12)-oic acid-(28)-methyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以8%的产率得到methyl 3β,11-dihydroxy-12-oxoolean-9(11),13(18)-diene-28-oate
  参考文献：
  名称：

  Zaprutko, Lucjusz; Gzella, Andrzej; Wrzeciono, Urszula, Liebigs Annalen der Chemie, 1990, # 4, p. 373 - 378

  摘要：

  DOI：
• 作为产物：
  描述：

  18α-H methyl 11-keto-oleanolate acetate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以61.4%的产率得到3β-hydroxy-11-oxo-18α-oleanen-(12)-oic acid-(28)-methyl ester
  参考文献：
  名称：

  三萜类化合物。第二部分 - 18β-和 18α-11-氧代齐墩果酸衍生物的碳 13 核磁共振谱

  摘要：

  已指定五对 18β- 和 18°-11-氧代齐墩果酸衍生物的 13C NMR 光谱。C-12、C-13、C-17、C-18 和 C-28 的化学位移对于 D/E 结立体化学的测定具有诊断价值。

  DOI：

  10.1002/mrc.1260250309

文献信息

• Kitasato, Acta Phytochimica, 1933, vol. 7, p. 180
  作者：Kitasato

  DOI：——

  日期：——
• Kitasato; Sone, Acta Phytochimica, 1932, vol. 6, p. 211
  作者：Kitasato、Sone

  DOI：——

  日期：——
• Zur Kenntnis der Triterpene. 42. Mitteilung. Über einige Keto-derivate der Oleanolsäure
  作者：L. Ruzicka、S. L. Cohen、M. Furter、F. Ch. van der Sluys-Veer

  DOI：10.1002/hlca.193802101211

  日期：——
• Triterpenoide. X. Über neue isomere Triterpenlactone
  作者：A. Gzella、L. Zaprutko、U. Wrzeciono

  DOI：10.1107/s0108270196012887

  日期：1997.2.15

  The X-ray crystal structure analyses of three new triterpene lactones (C29H42O6), namely 9 beta-hydroxy-28-methoxy-11,28-dioxo-1,2-dinor-10 alpha,18 beta-olean-12-en-3-10 beta-olide, (3), and its 18 alpha- and 9 alpha,18 alpha-isomers, (4) and (5) [9 beta-hydroxy-28-methoxy-11,28-dioxo-1,2-dinor-10 alpha,18 alpha-olean-12-en-3,10 beta-olide and 9 alpha-hydroxy-28-methoxy-11,28-dioxo-1,2-dinor-10 alpha,18 alpha-olean-12-en-3,10 beta-olide, respectively], are described. Compounds(3)-(5) were obtained by treatment of 3 beta-hydroxy-11-oxo-18 alpha-olean-12-en-28-oic acid methyl ester, (1), with sodium dichromate in acetic acid. In compounds (3)-(5), the six-membered ring A of (1) is replaced by a gamma-lactone ring. In contrast to compound (1), the C25 methyl group at C10 has an alpha configuration. The newly introduced hydroxyl group at C9 is beta oriented in compounds (3) and (4), and alpha oriented in (5). Ring B in (3) has a boat form, but in (4) and (5) it has different equivalent chair conformations. Ring C in (3) has a sofa form, in (4), it has a slightly distorted half-chair form and in (5), it has a conformation intermediate between the half-chair and sofa forms. Rings D and E have chair conformations in all three compounds and are trans-fused in compounds (4), (5) and (1), and cis-fused in (3). In contrast to compound (1), rings A/B in compounds (3)-(5) and rings BIC in compounds (3) and (4) are cis-fused. In compounds (3)-(5), formation of hydrogen bonds has been observed. Inversion of the alpha configuration to a beta configuration at C18 in oleanolic acid derivatives [transformation of (1) to (3)] has been observed for the first time. The triterpene lactones (3)(5) are the first known oleanane derivatives with cis-fused A/B [(3)-(5)] and B/C rings [(3) and (4)].
• ZAPRUTKO, LUCJUSZ;GZELLA, ANDRZEJ;WRZECIONO, URSZULA, LIEBIGS ANN. CHEM.,(1990) N, C. 373-378
  作者：ZAPRUTKO, LUCJUSZ、GZELLA, ANDRZEJ、WRZECIONO, URSZULA

  DOI：——

  日期：——