trans-Octahydro-3a-methyl-2(1H)-azulenone | 74676-02-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-Octahydro-3a-methyl-2(1H)-azulenone
• 英文别名: trans-1-methylbicyclo<5.3.0>decan-9-one；(3aR,8aR)-8a-methyl-1,3,3a,4,5,6,7,8-octahydroazulen-2-one
• CAS: 74676-02-1；74676-05-4；92286-88-9
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: QDUBQCGOONTUGL-MWLCHTKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  Methyl (2E/Z,3aα,8aβ)-2-butylideneoctahydro-3a(1H)-azulenecarboxylate 在 吡啶 、 lithium aluminium tetrahydride 、 二甲基硫 、 三乙基硼氢化锂 、 臭氧 作用下， 以 四氢呋喃 为溶剂， 反应 68.08h， 生成 trans-Octahydro-3a-methyl-2(1H)-azulenone
  参考文献：
  名称：

  Formation of trans ring-fused compounds by an alkylation-radical cyclization sequence

  摘要：

  Enolates derived from bicyclic lactones of type 1 (Scheme I) can be alkylated with 2-propynylic halides to give products 2, in which the unsaturated alkyl group is syn to the adjacent ring-fusion hydrogen. Reaction of 2 with sodium phenyl selenide and then with diazomethane produces esters 3, and these give trans ring-fused bicyclic compounds 4 when treated with triphenyltin hydride in the presence of a radical initiator. The bicyclic compounds afford ketones on double-bond cleavage, and the angular ester function can be converted into a methyl group. Similar processes occur if an aldehyde is used in the first step instead of a halide. The methodology is general.

  DOI：

  10.1021/jo00076a057

文献信息

• Palladium(II)-promoted cyclizations of olefinic silyl enol ethers. Preparations of .sigma.-(1-substituted 3-oxocyclopentyl)methylpalladium(II) complexes and their oxidative rearrangements
  作者：Yoshihiko Ito、Hirokazu Aoyama、Takeo Saegusa

  DOI：10.1021/ja00533a038

  日期：1980.6