5α,8α-epoxy-8β-methyl-2-methylene-1β,7β-bicyclo[3.5.0]decan-5β-ol | 177314-57-7

• 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: 5α,8α-epoxy-8β-methyl-2-methylene-1β,7β-bicyclo[3.5.0]decan-5β-ol
• 英文别名: (1R,4S,8S,10S)-1-methyl-5-methylidene-11-oxatricyclo[6.2.1.04,10]undecan-8-ol
• CAS: 177314-57-7
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: BGVLJDGNTNXOKJ-KXNHARMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5α,8α-epoxy-8β-methyl-2-methylene-1β,7β-bicyclo[3.5.0]decan-5β-ol 在 四甲基乙二胺 、 甲基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.25h， 生成 8β-methyl-2-methylene-1β,7β-bicyclo[3.5.0]dec-4-en-8α-ol
  参考文献：
  名称：

  Total Synthesis of Dictamnol, a Trinor-Guaiane Type Sesquiterpene from the Roots of Dictamnus dasycarpus TURCZ.

  摘要：

  Dictamnol (1), a trinor-guaiane type seequiterpene from the roots of Dictamnus dasycarpus TURCZ., was synthesized from 4α-acetoxy-3, 4, 4a, 5, 6, 8aβ-hexahydro-4aα-methyl-2H, 8H-naphthalene-1, 7-dione (3) by the utilization of an intramolecular base-induced rearrangement with sodium tert-amylate as a key step (27→28). Compound 3 was prepared from a chiral dione, (S)3, 4, 8, 8a-tetrahydro-8aα-methyl-2H, 7H-naphthalene-1, 6-dione (2) according to the procedure of de Groot et al. [J. Org. Chem., 48, 4380 (1983)] and was transformed into dictamnol (1) via 22, 23, 24, 26, 27, 28, and 30. Thus, the absolute configuration of dictamnol is as represented by formula 1.

  DOI：

  10.1248/cpb.44.646
• 作为产物：
  描述：

  8β-methyl-2-methylene-1β,7β-bicyclo[3.5.0]decane-5,8α-diol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以98.3%的产率得到5α,8α-epoxy-8β-methyl-2-methylene-1β,7β-bicyclo[3.5.0]decan-5β-ol
  参考文献：
  名称：

  Total Synthesis of Dictamnol, a Trinor-Guaiane Type Sesquiterpene from the Roots of Dictamnus dasycarpus TURCZ.

  摘要：

  Dictamnol (1), a trinor-guaiane type seequiterpene from the roots of Dictamnus dasycarpus TURCZ., was synthesized from 4α-acetoxy-3, 4, 4a, 5, 6, 8aβ-hexahydro-4aα-methyl-2H, 8H-naphthalene-1, 7-dione (3) by the utilization of an intramolecular base-induced rearrangement with sodium tert-amylate as a key step (27→28). Compound 3 was prepared from a chiral dione, (S)3, 4, 8, 8a-tetrahydro-8aα-methyl-2H, 7H-naphthalene-1, 6-dione (2) according to the procedure of de Groot et al. [J. Org. Chem., 48, 4380 (1983)] and was transformed into dictamnol (1) via 22, 23, 24, 26, 27, 28, and 30. Thus, the absolute configuration of dictamnol is as represented by formula 1.

  DOI：

  10.1248/cpb.44.646