(+/-)-4-methyl-7-methylene-3,4,5,6,7,8-hexahydroazulen-1(2H)-one | 146644-12-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-4-methyl-7-methylene-3,4,5,6,7,8-hexahydroazulen-1(2H)-one
• 英文别名: 4-Methyl-7-methylidene-2,3,4,5,6,8-hexahydroazulen-1-one
• CAS: 146644-12-4
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: YLCLGGQOXFWKRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (+/-)-4-methyl-7-methylene-3,4,5,6,7,8-hexahydroazulen-1(2H)-one 在 platinum(IV) oxide sodium hydroxide 、 氨 、 双氧水 、 氧气 、 二甲基氯化铝 、 lithium 、 diborane(6) 作用下， 以 正己烷 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 33.0h， 生成 (+/-)-(3aR*,4aS*,5R*,7aS*,8R*,9aS*)-3a,4,4a,5,6,7,7a,8,9,9a-decahydro-4a,8-dimethylazuleno<6,5-b>furan-2(3H)-one
  参考文献：
  名称：

  Allylsilane-based annulations. Direct stereoselective syntheses of (.+-.)-graveolide and (.+-.)-aromaticin

  摘要：

  An allylsilane-based annulation was used to construct a functionalized perhydroazulene. The C(1), C(5), and C(10) stereocenters, characteristic of the helenanolides, were established using a reductive alkylation strategy. Stereoselective syntheses of the pseudoguaianolides graveolide and aromaticin were achieved.

  DOI：

  10.1021/jo00057a012
• 作为产物：
  描述：

  3-(1-methylethenyl)-2-<2-<(trimethylsilyl)methyl>allyl>-2-cyclopenten-1-one 在 二氯乙基铝 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以77%的产率得到(+/-)-4-methyl-7-methylene-3,4,5,6,7,8-hexahydroazulen-1(2H)-one
  参考文献：
  名称：

  Allylsilane-based annulations. Direct stereoselective syntheses of (.+-.)-graveolide and (.+-.)-aromaticin

  摘要：

  An allylsilane-based annulation was used to construct a functionalized perhydroazulene. The C(1), C(5), and C(10) stereocenters, characteristic of the helenanolides, were established using a reductive alkylation strategy. Stereoselective syntheses of the pseudoguaianolides graveolide and aromaticin were achieved.

  DOI：

  10.1021/jo00057a012

文献信息

• Allylsilane-based annulations. Direct stereoselective syntheses of (.+-.)-graveolide and (.+-.)-aromaticin
  作者：George Majetich、Jee Seop Song、Alistair J. Leigh、Stephen M. Condon

  DOI：10.1021/jo00057a012

  日期：1993.2

  An allylsilane-based annulation was used to construct a functionalized perhydroazulene. The C(1), C(5), and C(10) stereocenters, characteristic of the helenanolides, were established using a reductive alkylation strategy. Stereoselective syntheses of the pseudoguaianolides graveolide and aromaticin were achieved.