(4aR,6bS,8aS,12aR,12bS,14bS)-4,4,6b,8a,9,9,12b,14b-Octamethyl-4a,5,6,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14b-hexadecahydro-4H-picen-3-one | 134028-32-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,6bS,8aS,12aR,12bS,14bS)-4,4,6b,8a,9,9,12b,14b-Octamethyl-4a,5,6,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14b-hexadecahydro-4H-picen-3-one
• 英文别名: (4aR,6aS,6bS,8aS,12aR,14bS)-4,4,6a,6b,8a,9,9,14b-octamethyl-5,6,7,8,10,11,12,12a,13,14-decahydro-4aH-picen-3-one
• CAS: 134028-32-3
• 化学式: C₃₀H₄₆O
• 分子量: 422.695
• InChiKey: JDMALDKFHILQAY-QQJZURGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  31
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  swertanone 在 硫酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 144.25h， 生成 (4aR,6bS,8aS,12aR,12bS,14bS)-4,4,6b,8a,9,9,12b,14b-Octamethyl-4a,5,6,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14b-hexadecahydro-4H-picen-3-one
  参考文献：
  名称：

  Peracid oxidation products of swertanone, the novel triterpene of Swertia chirata

  摘要：

  While treatment of swertanone (1a) with mineral acids and Lewis acids yielded isoswertanone (2a) as the only isolable product, its reaction with m-chloroperbenzoic acid afforded 7-alpha, 8-alpha-epoxyswertanone (7), 7-alpha -hydroxy-swert-8-en-3-one (8), swerta-7, 9(11)-dien-3-one (3a), its 7-alpha, 8-alpha -epoxide (4a), 7-alpha -hydroxy-friedogammacer-14-en-3-one (5a) and its 14-alpha, 15-alpha -epoxide (6a). The structures of the products have been elucidated mainly on the basis of H-1 and C-13 NMR spectroscopy and, in some cases, by chemical correlation.Assignments of C-13 NMR signals of the products have been done and those of some of the signals of 1a, swertenyl acetate (1b) and swertenol (16) have been revised. In this connection, spectra of bauerenyl acetate (18), isobauerenyl acetate (19) and multiflorenyl acetate (20) have been recorded.

  DOI：

  10.1016/s0040-4020(01)96141-1