methyl (2S)-2-[(5R,8R,8aR)-8-hydroxy-3,8-dimethyl-2-oxo-1,4,5,6,7,8a-hexahydroazulen-5-yl]propanoate | 23515-82-4

• 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: methyl (2S)-2-[(5R,8R,8aR)-8-hydroxy-3,8-dimethyl-2-oxo-1,4,5,6,7,8a-hexahydroazulen-5-yl]propanoate
• CAS: 23515-82-4
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: GRWGGPYMFGMRDD-RKTKGFPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Isophoto-α-santoninlacton 在 溶剂黄146 、 锌 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 生成 methyl (2S)-2-[(5R,8R,8aR)-8-hydroxy-3,8-dimethyl-2-oxo-1,4,5,6,7,8a-hexahydroazulen-5-yl]propanoate
  参考文献：
  名称：

  Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones. Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin

  摘要：

  Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00986-3

文献信息

• Stereoselective synthesis of α-bulnesene, 4-epi-α-bulnesene, and 5-epi-α-bulnesene
  作者：Edward Piers、Kin Fai Cheng

  DOI：10.1139/v70-372

  日期：1970.7.15

  Lithium-ammonia reduction of the hydroguaiazulene derivative 6, followed by oxidation of the resulting diol 13, gave, in a highly stereoselective manner, the keto alcohol 14. The latter was converted into 5-epi-a-bulnesene (2). In a similar sequence of reactions, 4-epi-a-bulnesene (3) was obtained from compound 9. Photochemical rearrangement of the previously obtained dienone 25 gave the hydroguaiazulene

  氢化愈创甘油醚衍生物 6 的锂-氨还原，然后氧化所得二醇 13，以高度立体选择性的方式得到酮醇 14。后者转化为 5-epi-a-bulnesene (2)。在类似的反应序列中，从化合物 9 中获得 4-epi-a-bulnesene (3)。先前获得的二烯酮 25 的光化学重排得到了氢愈创甘油醚衍生物 27。后者依次进行乙酰化、氢化和硼氢化钠还原得到差向异构二醇 31 和 32 的混合物。当该混合物用吡啶中的对甲苯磺酸处理时，所得烯烃二酯 35 依次进行氢化 [三(三苯基膦) 氯铑] 和氢化铝锂还原，结晶得到二醇37。