2-formyl-3-oxoolean-12-en-28-oic acid methyl ester | 90544-35-7

• 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: 2-formyl-3-oxoolean-12-en-28-oic acid methyl ester
• 英文别名: (+)-2ξ-formyl-3-oxo-olean-12-en-28-oic acid methyl ester；(+)-2ξ-Formyl-3-oxo-olean-12-en-28-saeure-methylester；3-Oxo-2ξ-formyl-oleanen-(12)-saeure-(28)-methylester
• CAS: 90544-35-7
• 化学式: C₃₂H₄₈O₄
• 分子量: 496.731
• InChiKey: DWHOUJGTKIOPDN-QFTGLFCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  36.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-formyl-3-oxoolean-12-en-28-oic acid methyl ester 在 盐酸羟胺 作用下， 以76.1%的产率得到olean-2,12-dieno<2,3-d>isoxazol-28-oic acid methyl ester
  参考文献：
  名称：

  Triterpenoide. XIV. [2,3-d]Isoxazoltriterpenderivate

  摘要：

  The X-ray crystal structure analyses of two triterpene isoxazoles, namely olean-2,12-dieno[2,3-d]isoxazol-28-oic acid methyl ester {methyl isoxazolo[4,5-b]olean-2,12-dien-28-oate, C32H47NO3, (2a)} and 19 beta,28-epoxy-18 alpha-olean-2-eno[2,3-d]isoxazole {19 beta,28-epoxy-isoxazolo[4,5-b]-18 alpha-olean-2-ene, C31H47NO2, (4a)} are described. These compounds were obtained by treatment of 2-formyl- or 2-hydroxymethylene derivatives of 3-oxoolean-12-en-28-oic methyl ester, (la) and (Ib), and 19 beta,28-epoxy-18H alpha-oleanan-3-one, (3a) and (3b), with hydroxylamine hydrochloride according to the method described by Govardhan, Reddy, Ramaiah & Rao [J. Indian Chem. Sac. (1983), pp. 858-860] for the synthesis of ring-A-fused triterpene [3,2-c]isoxazoles. The structures of the obtained [2,3-d]isoxazoles, (2a) and (4a), were confirmed by the comparison of the bond lengths and bond angles found for the isoxazole rings of compounds (2a) and (4a) with the corresponding data given in the literature. The isoxazole rings in both compounds are planar. Ring A in (2a) and (4a) has a conformation between the half-chair and sofa form. Rings B, D and E in (2a), and B, C, D and E in (4a) have the chair conformation. Ring C in (2a) has a distorted sofa form. In (2a), the rings A/B, B/C and C/D are trans-fused and the rings D/E cis-fused, In (4a), the A/B, B/C, C/D and D/E ring junctions are trans. The axial O2 and C28 atoms in (4a) are beta oriented and form, together with the C17, C18 and C19 atoms, the five-membered ring F, which has an envelope conformation.

  DOI：

  10.1107/s010827019900013x
• 作为产物：
  描述：

  齐墩果酸甲酯 在 chromium(VI) oxide 、 乙醚 、 sodium ethanolate 、 溶剂黄146 作用下， 生成 2-formyl-3-oxoolean-12-en-28-oic acid methyl ester
  参考文献：
  名称：

  Polyterpene and Polyterpenoide C.ÜberUmsetzungen an den Ringen and E derOleanolsäure。北三叶草肯特尼斯desKohlenstoffgerüstes五环萜三萜

  摘要：

  DOI：

  10.1002/hlca.19360190118

文献信息

• Terpenoids. XXXI.¹ The Structure and Stereochemistry of Medicagenic Acid²
  作者：Carl Djerassi、D. B. Thomas、A. L. Livingston、C. Ray Thompson

  DOI：10.1021/ja01576a057

  日期：1957.10