2-methylene-1β,7β-bicyclo[3.5.0]dec-5-en-8-one | 177093-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methylene-1β,7β-bicyclo[3.5.0]dec-5-en-8-one
• 英文别名: (3aS,8aS)-4-methylidene-2,3,3a,5,6,8a-hexahydroazulen-1-one
• CAS: 177093-36-6
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: FYGXDOQHNOIVBF-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylene-1β,7β-bicyclo[3.5.0]dec-5-en-8-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 26.0h， 生成 8α-acetoxy-8β-methyl-2-methylene-1β,7β-bicyclo[3.5.0]dec-5-ene
  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：

  2-methylene-1β,7β-bicyclo[3.5.0]dec-5-en-8-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 0.05h， 以71.5%的产率得到2-methylene-1β,7β-bicyclo[3.5.0]dec-5-en-8-one
  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